# 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_13a
_database_code_depnum_ccdc_archive 'CCDC 1045940'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-2,7(1H,6H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N5 O2 S'
_chemical_formula_sum            'C8 H11 N5 O2 S'
_chemical_formula_weight         241.28

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   6.8510(5)
_cell_length_b                   7.7360(6)
_cell_length_c                   19.3150(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.218(2)
_cell_angle_gamma                90.00
_cell_volume                     1019.44(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2058
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8078
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2712
_reflns_number_gt                2192
_reflns_threshold_expression     I>2/s(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'

_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)+(0.0507P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
S1 S 0.76058(6) 0.03735(5) 1.02485(2) 0.01609(11) Uani 1 1 d . . .
O1 O 1.34506(16) 0.24268(15) 0.84731(6) 0.0175(3) Uani 1 1 d . . .
O2 O 0.63100(19) -0.27194(15) 0.86930(6) 0.0228(3) Uani 1 1 d . . .
N1 N 1.03725(19) 0.12662(17) 0.81695(7) 0.0139(3) Uani 1 1 d . . .
N2 N 1.0569(2) 0.39317(17) 0.85976(7) 0.0153(3) Uani 1 1 d . . .
N3 N 0.6950(2) 0.06143(17) 0.81931(7) 0.0147(3) Uani 1 1 d . . .
H3N H 0.5754 0.1050 0.8142 0.018 Uiso 1 1 d R . .
N4 N 0.71437(19) 0.01152(17) 0.89022(7) 0.0141(3) Uani 1 1 d . . .
N5 N 0.82354(19) 0.28683(17) 0.93313(7) 0.0150(3) Uani 1 1 d . . .
C1 C 0.8391(2) 0.1949(2) 0.80806(8) 0.0139(3) Uani 1 1 d . . .
H1A H 0.8125 0.2436 0.7602 0.017 Uiso 1 1 calc R . .
C2 C 1.1651(2) 0.25326(19) 0.84180(8) 0.0137(3) Uani 1 1 d . . .
C3 C 0.8524(2) 0.3425(2) 0.86148(8) 0.0146(3) Uani 1 1 d . . .
H3A H 0.7620 0.4395 0.8462 0.018 Uiso 1 1 calc R . .
C4 C 0.6822(2) -0.1562(2) 0.90948(8) 0.0161(3) Uani 1 1 d . . .
C5 C 0.7225(2) -0.1769(2) 0.98723(8) 0.0172(3) Uani 1 1 d . . .
H5A H 0.8405 -0.2491 0.9982 0.021 Uiso 1 1 calc R . .
H5B H 0.6100 -0.2339 1.0066 0.021 Uiso 1 1 calc R . .
C6 C 0.7692(2) 0.1323(2) 0.94191(8) 0.0134(3) Uani 1 1 d . . .
C7 C 1.0987(3) -0.0138(2) 0.77379(9) 0.0193(3) Uani 1 1 d . . .
H7A H 1.2377 -0.0387 0.7861 0.029 Uiso 1 1 calc R . .
H7B H 1.0788 0.0199 0.7247 0.029 Uiso 1 1 calc R . .
H7C H 1.0208 -0.1172 0.7814 0.029 Uiso 1 1 calc R . .
C8 C 1.1425(3) 0.5385(2) 0.89927(9) 0.0202(3) Uani 1 1 d . . .
H8A H 1.2848 0.5389 0.8969 0.030 Uiso 1 1 calc R . .
H8B H 1.1137 0.5282 0.9479 0.030 Uiso 1 1 calc R . .
H8C H 1.0869 0.6466 0.8797 0.030 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7683(16) . ?
S1 C5 1.8188(17) . ?
O1 C2 1.2306(19) . ?
O2 C4 1.215(2) . ?
N1 C2 1.371(2) . ?
N1 C1 1.4522(19) . ?
N1 C7 1.455(2) . ?
N2 C2 1.374(2) . ?
N2 C8 1.453(2) . ?
N2 C3 1.458(2) . ?
N3 N4 1.4176(18) . ?
N3 C1 1.458(2) . ?
N3 H3N 0.8827 . ?
N4 C4 1.373(2) . ?
N4 C6 1.394(2) . ?
N5 C6 1.268(2) . ?
N5 C3 1.480(2) . ?
C1 C3 1.536(2) . ?
C1 H1A 1.0000 . ?
C3 H3A 1.0000 . ?
C4 C5 1.510(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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 C5 91.83(7) . . ?
C2 N1 C1 110.01(12) . . ?
C2 N1 C7 121.69(13) . . ?
C1 N1 C7 121.31(13) . . ?
C2 N2 C8 122.74(14) . . ?
C2 N2 C3 109.62(13) . . ?
C8 N2 C3 122.64(13) . . ?
N4 N3 C1 109.35(12) . . ?
N4 N3 H3N 102.5 . . ?
C1 N3 H3N 110.3 . . ?
C4 N4 C6 118.61(13) . . ?
C4 N4 N3 121.06(13) . . ?
C6 N4 N3 120.33(13) . . ?
C6 N5 C3 117.74(13) . . ?
N1 C1 N3 111.31(12) . . ?
N1 C1 C3 101.14(12) . . ?
N3 C1 C3 115.20(13) . . ?
N1 C1 H1A 109.6 . . ?
N3 C1 H1A 109.6 . . ?
C3 C1 H1A 109.6 . . ?
O1 C2 N1 125.86(14) . . ?
O1 C2 N2 126.15(14) . . ?
N1 C2 N2 107.99(13) . . ?
N2 C3 N5 108.05(12) . . ?
N2 C3 C1 100.54(12) . . ?
N5 C3 C1 114.01(13) . . ?
N2 C3 H3A 111.2 . . ?
N5 C3 H3A 111.2 . . ?
C1 C3 H3A 111.2 . . ?
O2 C4 N4 124.55(15) . . ?
O2 C4 C5 124.97(15) . . ?
N4 C4 C5 110.48(14) . . ?
C4 C5 S1 107.91(11) . . ?
C4 C5 H5A 110.1 . . ?
S1 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
S1 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N5 C6 N4 126.83(15) . . ?
N5 C6 S1 123.19(12) . . ?
N4 C6 S1 109.95(11) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N3 N4 C4 -145.46(14) . . . . ?
C1 N3 N4 C6 33.72(18) . . . . ?
C2 N1 C1 N3 -148.79(13) . . . . ?
C7 N1 C1 N3 60.07(19) . . . . ?
C2 N1 C1 C3 -25.93(16) . . . . ?
C7 N1 C1 C3 -177.07(14) . . . . ?
N4 N3 C1 N1 67.37(15) . . . . ?
N4 N3 C1 C3 -47.01(16) . . . . ?
C1 N1 C2 O1 -171.17(15) . . . . ?
C7 N1 C2 O1 -20.2(2) . . . . ?
C1 N1 C2 N2 9.18(17) . . . . ?
C7 N1 C2 N2 160.19(14) . . . . ?
C8 N2 C2 O1 -10.9(2) . . . . ?
C3 N2 C2 O1 -166.41(15) . . . . ?
C8 N2 C2 N1 168.71(14) . . . . ?
C3 N2 C2 N1 13.23(17) . . . . ?
C2 N2 C3 N5 91.52(15) . . . . ?
C8 N2 C3 N5 -63.98(18) . . . . ?
C2 N2 C3 C1 -28.21(16) . . . . ?
C8 N2 C3 C1 176.29(14) . . . . ?
C6 N5 C3 N2 -118.88(15) . . . . ?
C6 N5 C3 C1 -8.04(19) . . . . ?
N1 C1 C3 N2 31.24(14) . . . . ?
N3 C1 C3 N2 151.37(13) . . . . ?
N1 C1 C3 N5 -84.10(15) . . . . ?
N3 C1 C3 N5 36.04(18) . . . . ?
C6 N4 C4 O2 178.80(15) . . . . ?
N3 N4 C4 O2 -2.0(2) . . . . ?
C6 N4 C4 C5 -2.10(19) . . . . ?
N3 N4 C4 C5 177.10(13) . . . . ?
O2 C4 C5 S1 -172.19(14) . . . . ?
N4 C4 C5 S1 8.70(16) . . . . ?
C6 S1 C5 C4 -10.10(12) . . . . ?
C3 N5 C6 N4 -6.8(2) . . . . ?
C3 N5 C6 S1 171.11(11) . . . . ?
C4 N4 C6 N5 172.32(15) . . . . ?
N3 N4 C6 N5 -6.9(2) . . . . ?
C4 N4 C6 S1 -5.83(17) . . . . ?
N3 N4 C6 S1 174.97(11) . . . . ?
C5 S1 C6 N5 -169.05(14) . . . . ?
C5 S1 C6 N4 9.18(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3N O1 1_455 0.88 2.05 2.8709(18) 153 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_14b
_database_code_depnum_ccdc_archive 'CCDC 1045941'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-2,8(3H,7H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 N5 O2 S, C H4 O'
_chemical_formula_sum            'C11 H19 N5 O3 S'
_chemical_formula_weight         301.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   '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                   26.710(4)
_cell_length_b                   7.5095(10)
_cell_length_c                   14.0757(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.942(2)
_cell_angle_gamma                90.00
_cell_volume                     2802.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3066
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10581
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         28.99
_reflns_number_total             3653
_reflns_number_gt                3251
_reflns_threshold_expression     I>2/s(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'

_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)+(0.0796P)²+0.6998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3653
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.451355(10) 0.16767(4) 1.00223(2) 0.01647(11) Uani 1 1 d . . .
O1 O 0.66759(3) 0.00309(13) 0.96313(7) 0.0242(2) Uani 1 1 d . . .
O2 O 0.56327(3) 0.30951(13) 1.18706(6) 0.0211(2) Uani 1 1 d . . .
N1 N 0.62987(4) 0.23879(14) 1.03204(7) 0.0167(2) Uani 1 1 d . . .
N2 N 0.60642(4) 0.17999(13) 0.87790(7) 0.0163(2) Uani 1 1 d . . .
N3 N 0.54129(4) 0.31367(13) 1.02531(7) 0.0136(2) Uani 1 1 d . . .
N4 N 0.50013(4) 0.30613(13) 0.86568(7) 0.0160(2) Uani 1 1 d . . .
N5 N 0.54115(4) 0.41107(14) 0.84304(7) 0.0166(2) Uani 1 1 d . . .
H5N H 0.5439 0.4076 0.7764 0.020 Uiso 1 1 d R . .
C1 C 0.59159(4) 0.36967(15) 1.00110(8) 0.0139(2) Uani 1 1 d . . .
H1A H 0.6010 0.4904 1.0273 0.017 Uiso 1 1 calc R . .
C2 C 0.63778(4) 0.12823(16) 0.95723(9) 0.0172(2) Uani 1 1 d . . .
C3 C 0.58996(4) 0.36489(15) 0.89167(8) 0.0148(2) Uani 1 1 d . . .
H3A H 0.6158 0.4489 0.8717 0.018 Uiso 1 1 calc R . .
C4 C 0.53350(4) 0.27295(16) 1.11781(8) 0.0155(2) Uani 1 1 d . . .
C5 C 0.48464(5) 0.17275(16) 1.12213(9) 0.0174(2) Uani 1 1 d . . .
H5A H 0.4640 0.2334 1.1662 0.021 Uiso 1 1 calc R . .
H5B H 0.4917 0.0500 1.1457 0.021 Uiso 1 1 calc R . .
C6 C 0.50200(4) 0.26972(15) 0.95443(8) 0.0136(2) Uani 1 1 d . . .
C7 C 0.66825(4) 0.26234(18) 1.11483(9) 0.0209(3) Uani 1 1 d . . .
H7A H 0.6845 0.1462 1.1319 0.025 Uiso 1 1 calc R . .
H7B H 0.6518 0.3036 1.1702 0.025 Uiso 1 1 calc R . .
C8 C 0.70841(5) 0.3962(2) 1.09477(11) 0.0305(3) Uani 1 1 d . . .
H8A H 0.7323 0.4128 1.1526 0.046 Uiso 1 1 calc R . .
H8B H 0.6924 0.5103 1.0759 0.046 Uiso 1 1 calc R . .
H8C H 0.7264 0.3517 1.0429 0.046 Uiso 1 1 calc R . .
C9 C 0.61084(5) 0.11014(18) 0.78255(9) 0.0210(3) Uani 1 1 d . . .
H9A H 0.5770 0.1094 0.7450 0.025 Uiso 1 1 calc R . .
H9B H 0.6228 -0.0146 0.7885 0.025 Uiso 1 1 calc R . .
C10 C 0.64662(6) 0.2166(2) 0.72851(11) 0.0319(3) Uani 1 1 d . . .
H10A H 0.6479 0.1633 0.6653 0.048 Uiso 1 1 calc R . .
H10B H 0.6804 0.2155 0.7645 0.048 Uiso 1 1 calc R . .
H10C H 0.6346 0.3397 0.7209 0.048 Uiso 1 1 calc R . .
O1S O 0.67424(4) -0.33128(14) 0.88312(10) 0.0389(3) Uani 1 1 d . . .
H1SO H 0.6698 -0.2174 0.9151 0.047 Uiso 1 1 d R . .
C1S C 0.72470(6) -0.3548(2) 0.86833(12) 0.0339(3) Uani 1 1 d . . .
H1SA H 0.7342 -0.2629 0.8244 0.051 Uiso 1 1 calc R . .
H1SB H 0.7290 -0.4727 0.8406 0.051 Uiso 1 1 calc R . .
H1SC H 0.7462 -0.3451 0.9296 0.051 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7578(12) . ?
S1 C5 1.8104(13) . ?
O1 C2 1.2281(15) . ?
O2 C4 1.2126(15) . ?
N1 C2 1.3771(17) . ?
N1 C1 1.4470(14) . ?
N1 C7 1.4667(14) . ?
N2 C2 1.3686(15) . ?
N2 C9 1.4590(16) . ?
N2 C3 1.4763(15) . ?
N3 C4 1.3774(15) . ?
N3 C6 1.3972(14) . ?
N3 C1 1.4862(14) . ?
N4 C6 1.2738(16) . ?
N4 N5 1.4169(14) . ?
N5 C3 1.4397(14) . ?
N5 H5N 0.9502 . ?
C1 C3 1.5361(16) . ?
C1 H1A 1.0000 . ?
C3 H3A 1.0000 . ?
C4 C5 1.5139(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 C8 1.5214(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5189(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1S C1S 1.3997(19) . ?
O1S H1SO 0.9801 . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?

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 C5 91.93(5) . . ?
C2 N1 C1 110.33(9) . . ?
C2 N1 C7 121.55(10) . . ?
C1 N1 C7 123.90(10) . . ?
C2 N2 C9 122.61(10) . . ?
C2 N2 C3 108.82(10) . . ?
C9 N2 C3 121.15(10) . . ?
C4 N3 C6 115.87(10) . . ?
C4 N3 C1 121.57(9) . . ?
C6 N3 C1 121.65(10) . . ?
C6 N4 N5 113.60(9) . . ?
N4 N5 C3 116.07(9) . . ?
N4 N5 H5N 111.2 . . ?
C3 N5 H5N 106.8 . . ?
N1 C1 N3 111.37(9) . . ?
N1 C1 C3 102.66(9) . . ?
N3 C1 C3 107.85(8) . . ?
N1 C1 H1A 111.5 . . ?
N3 C1 H1A 111.5 . . ?
C3 C1 H1A 111.5 . . ?
O1 C2 N2 126.89(12) . . ?
O1 C2 N1 124.59(11) . . ?
N2 C2 N1 108.51(10) . . ?
N5 C3 N2 115.54(9) . . ?
N5 C3 C1 112.67(10) . . ?
N2 C3 C1 100.42(9) . . ?
N5 C3 H3A 109.3 . . ?
N2 C3 H3A 109.3 . . ?
C1 C3 H3A 109.3 . . ?
O2 C4 N3 123.39(11) . . ?
O2 C4 C5 124.40(11) . . ?
N3 C4 C5 112.19(10) . . ?
C4 C5 S1 107.56(8) . . ?
C4 C5 H5A 110.2 . . ?
S1 C5 H5A 110.2 . . ?
C4 C5 H5B 110.2 . . ?
S1 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
N4 C6 N3 125.92(11) . . ?
N4 C6 S1 121.88(8) . . ?
N3 C6 S1 112.08(9) . . ?
N1 C7 C8 111.90(11) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 113.40(11) . . ?
N2 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1S O1S H1SO 110.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N4 N5 C3 41.15(14) . . . . ?
C2 N1 C1 N3 96.88(11) . . . . ?
C7 N1 C1 N3 -106.00(12) . . . . ?
C2 N1 C1 C3 -18.29(12) . . . . ?
C7 N1 C1 C3 138.83(11) . . . . ?
C4 N3 C1 N1 55.96(14) . . . . ?
C6 N3 C1 N1 -112.68(11) . . . . ?
C4 N3 C1 C3 167.88(10) . . . . ?
C6 N3 C1 C3 -0.76(14) . . . . ?
C9 N2 C2 O1 -11.46(19) . . . . ?
C3 N2 C2 O1 -161.57(12) . . . . ?
C9 N2 C2 N1 169.74(11) . . . . ?
C3 N2 C2 N1 19.63(13) . . . . ?
C1 N1 C2 O1 -178.81(11) . . . . ?
C7 N1 C2 O1 23.43(18) . . . . ?
C1 N1 C2 N2 0.03(13) . . . . ?
C7 N1 C2 N2 -157.73(11) . . . . ?
N4 N5 C3 N2 57.76(14) . . . . ?
N4 N5 C3 C1 -56.87(13) . . . . ?
C2 N2 C3 N5 -150.99(10) . . . . ?
C9 N2 C3 N5 58.39(14) . . . . ?
C2 N2 C3 C1 -29.51(11) . . . . ?
C9 N2 C3 C1 179.87(10) . . . . ?
N1 C1 C3 N5 151.16(9) . . . . ?
N3 C1 C3 N5 33.47(13) . . . . ?
N1 C1 C3 N2 27.67(11) . . . . ?
N3 C1 C3 N2 -90.02(10) . . . . ?
C6 N3 C4 O2 -176.96(11) . . . . ?
C1 N3 C4 O2 13.78(18) . . . . ?
C6 N3 C4 C5 4.92(14) . . . . ?
C1 N3 C4 C5 -164.34(10) . . . . ?
O2 C4 C5 S1 175.39(10) . . . . ?
N3 C4 C5 S1 -6.51(12) . . . . ?
C6 S1 C5 C4 5.07(8) . . . . ?
N5 N4 C6 N3 -4.45(16) . . . . ?
N5 N4 C6 S1 171.19(8) . . . . ?
C4 N3 C6 N4 175.16(11) . . . . ?
C1 N3 C6 N4 -15.59(17) . . . . ?
C4 N3 C6 S1 -0.85(12) . . . . ?
C1 N3 C6 S1 168.41(8) . . . . ?
C5 S1 C6 N4 -178.89(10) . . . . ?
C5 S1 C6 N3 -2.70(9) . . . . ?
C2 N1 C7 C8 81.60(15) . . . . ?
C1 N1 C7 C8 -73.07(15) . . . . ?
C2 N2 C9 C10 -88.81(15) . . . . ?
C3 N2 C9 C10 57.74(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1S H1SO O1 1_555 0.98 1.79 2.7664(15) 172 ?
N5 H5N N4 2_656 0.95 2.32 3.1121(15) 140 ?
N5 H5N O2 6_565 0.95 2.55 3.1442(14) 121 ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.069

