# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_La
_database_code_depnum_ccdc_archive 'CCDC 1420844'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 S2'
_chemical_formula_sum            'C16 H18 N4 S2'
_chemical_formula_weight         330.46

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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 '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                   19.017(2)
_cell_length_b                   5.1090(5)
_cell_length_c                   17.805(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.507(12)
_cell_angle_gamma                90.00
_cell_volume                     1706.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4292
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            8821
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1522
_reflns_number_gt                1217
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+12.0000P] 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         1522
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38288(7) 0.0922(3) 0.67809(7) 0.0650(4) Uani 1 1 d . . .
C4 C 0.3140(2) 0.1177(8) 0.5994(2) 0.0400(9) Uani 1 1 d . . .
C3 C 0.2862(3) 0.4273(11) 0.6760(3) 0.0633(13) Uani 1 1 d . . .
H3 H 0.2588 0.5639 0.6900 0.076 Uiso 1 1 calc R . .
C2 C 0.3440(3) 0.3434(11) 0.7221(3) 0.0641(14) Uani 1 1 d . . .
C1 C 0.3766(4) 0.4425(14) 0.7999(3) 0.101(2) Uani 1 1 d . . .
H1A H 0.4245 0.5003 0.7989 0.151 Uiso 1 1 calc R . .
H1B H 0.3772 0.3042 0.8365 0.151 Uiso 1 1 calc R . .
H1C H 0.3489 0.5862 0.8138 0.151 Uiso 1 1 calc R . .
C6 C 0.4361(2) -0.1065(8) 0.5156(2) 0.0441(10) Uani 1 1 d . . .
C7 C 0.4354(2) 0.1007(10) 0.4653(3) 0.0566(12) Uani 1 1 d . . .
H7 H 0.3923 0.1697 0.4412 0.068 Uiso 1 1 calc R . .
C5 C 0.3666(2) -0.2273(9) 0.5306(3) 0.0515(11) Uani 1 1 d . . .
H5A H 0.3489 -0.3450 0.4890 0.062 Uiso 1 1 calc R . .
H5B H 0.3764 -0.3311 0.5768 0.062 Uiso 1 1 calc R . .
C8 C 0.5005(2) -0.2055(9) 0.5492(3) 0.0537(12) Uani 1 1 d . . .
H8 H 0.5015 -0.3461 0.5825 0.064 Uiso 1 1 calc R . .
N2 N 0.31109(18) -0.0394(7) 0.5387(2) 0.0508(10) Uani 1 1 d . . .
H2 H 0.2748 -0.0284 0.5030 0.061 Uiso 1 1 calc R . .
N1 N 0.26819(19) 0.3028(8) 0.6057(2) 0.0540(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0663(8) 0.0686(9) 0.0523(8) -0.0042(6) -0.0134(6) 0.0033(7)
C4 0.035(2) 0.048(2) 0.037(2) 0.0043(19) 0.0042(16) -0.0058(19)
C3 0.074(3) 0.065(3) 0.054(3) -0.006(3) 0.019(3) 0.000(3)
C2 0.084(4) 0.064(3) 0.043(3) -0.004(2) 0.004(2) -0.012(3)
C1 0.138(6) 0.103(5) 0.053(4) -0.019(3) -0.007(3) -0.007(5)
C6 0.041(2) 0.045(2) 0.045(2) -0.002(2) 0.0046(18) 0.0020(19)
C7 0.041(2) 0.061(3) 0.065(3) 0.014(2) 0.002(2) 0.007(2)
C5 0.046(2) 0.051(3) 0.057(3) -0.005(2) 0.009(2) -0.004(2)
C8 0.050(3) 0.053(3) 0.056(3) 0.015(2) 0.003(2) 0.001(2)
N2 0.0379(18) 0.062(2) 0.050(2) -0.0120(19) 0.0004(15) -0.0021(17)
N1 0.048(2) 0.064(3) 0.051(2) -0.0064(19) 0.0103(17) 0.0001(19)

_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 C2 1.732(6) . ?
S1 C4 1.758(4) . ?
C4 N1 1.303(5) . ?
C4 N2 1.340(5) . ?
C3 C2 1.329(7) . ?
C3 N1 1.394(6) . ?
C2 C1 1.510(7) . ?
C6 C8 1.367(6) . ?
C6 C7 1.385(6) . ?
C6 C5 1.523(6) . ?
C7 C8 1.394(6) 5_656 ?
C5 N2 1.452(5) . ?
C8 C7 1.394(6) 5_656 ?

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 S1 C4 89.3(2) . . ?
N1 C4 N2 124.5(4) . . ?
N1 C4 S1 113.9(3) . . ?
N2 C4 S1 121.6(3) . . ?
C2 C3 N1 117.6(5) . . ?
C3 C2 C1 129.1(6) . . ?
C3 C2 S1 109.3(4) . . ?
C1 C2 S1 121.5(5) . . ?
C8 C6 C7 118.6(4) . . ?
C8 C6 C5 120.9(4) . . ?
C7 C6 C5 120.5(4) . . ?
C6 C7 C8 119.9(4) . 5_656 ?
N2 C5 C6 114.6(4) . . ?
C6 C8 C7 121.6(4) . 5_656 ?
C4 N2 C5 122.9(4) . . ?
C4 N1 C3 109.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_Lb
_database_code_depnum_ccdc_archive 'CCDC 1420845'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 S2'
_chemical_formula_sum            'C16 H18 N4 S2'
_chemical_formula_weight         330.46

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'
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   ' 	I 2/c'
_symmetry_space_group_name_Hall  '-I 2yc'

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

_cell_length_a                   13.4747(14)
_cell_length_b                   9.6657(10)
_cell_length_c                   13.4889(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.678(8)
_cell_angle_gamma                90.00
_cell_volume                     1691.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3716
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      26.85

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            9560
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.23
_reflns_number_total             1518
_reflns_number_gt                1273
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.3000P] 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         1518
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33771(4) 0.17117(5) -0.04484(4) 0.0512(3) Uani 1 1 d . . .
N1 N 0.36585(11) 0.43421(16) -0.05347(11) 0.0476(4) Uani 1 1 d . . .
N2 N 0.50817(12) 0.31732(15) 0.05247(13) 0.0514(5) Uani 1 1 d . . .
H2 H 0.5400 0.3942 0.0706 0.062 Uiso 1 1 calc R . .
C7 C 0.65771(15) 0.2961(2) 0.26182(16) 0.0527(5) Uani 1 1 d . . .
H7 H 0.5953 0.3274 0.2704 0.063 Uiso 1 1 calc R . .
C8 C 0.75216(15) 0.17434(18) 0.16374(15) 0.0476(5) Uani 1 1 d . . .
H8 H 0.7546 0.1230 0.1061 0.057 Uiso 1 1 calc R . .
C6 C 0.65840(13) 0.22030(18) 0.17410(14) 0.0426(5) Uani 1 1 d . . .
C5 C 0.55956(16) 0.18938(19) 0.09235(18) 0.0537(6) Uani 1 1 d . . .
H5A H 0.5749 0.1373 0.0368 0.064 Uiso 1 1 calc R . .
H5B H 0.5146 0.1337 0.1216 0.064 Uiso 1 1 calc R . .
C2 C 0.23641(13) 0.2713(2) -0.11666(14) 0.0483(5) Uani 1 1 d . . .
C3 C 0.26721(14) 0.4041(2) -0.11177(14) 0.0498(5) Uani 1 1 d . . .
H3 H 0.2235 0.4733 -0.1465 0.060 Uiso 1 1 calc R . .
C4 C 0.41198(14) 0.32051(16) -0.01218(15) 0.0408(5) Uani 1 1 d . . .
C1 C 0.13420(17) 0.2081(3) -0.17081(19) 0.0665(6) Uani 1 1 d . . .
H1A H 0.0875 0.2796 -0.2040 0.100 Uiso 1 1 calc R . .
H1B H 0.1064 0.1612 -0.1216 0.100 Uiso 1 1 calc R . .
H1C H 0.1434 0.1432 -0.2215 0.100 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0386(4) 0.0415(4) 0.0626(4) -0.00171(18) -0.0051(3) -0.00564(17)
N1 0.0356(8) 0.0433(9) 0.0545(9) 0.0071(6) -0.0036(7) -0.0001(6)
N2 0.0355(9) 0.0385(8) 0.0644(11) 0.0062(7) -0.0138(8) -0.0045(6)
C7 0.0299(10) 0.0570(12) 0.0665(13) -0.0029(9) 0.0051(9) 0.0030(8)
C8 0.0417(11) 0.0479(11) 0.0500(11) -0.0013(8) 0.0068(9) 0.0002(7)
C6 0.0318(10) 0.0377(9) 0.0504(10) 0.0069(8) -0.0026(8) -0.0003(7)
C5 0.0412(11) 0.0398(10) 0.0656(13) 0.0044(8) -0.0107(9) 0.0029(7)
C2 0.0317(10) 0.0595(12) 0.0464(11) -0.0019(8) -0.0018(8) -0.0013(8)
C3 0.0352(10) 0.0556(12) 0.0503(11) 0.0054(8) -0.0028(8) 0.0066(8)
C4 0.0322(10) 0.0408(10) 0.0435(10) 0.0013(7) 0.0002(8) -0.0029(7)
C1 0.0369(11) 0.0861(16) 0.0641(14) -0.0048(12) -0.0075(10) -0.0120(11)

_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 C2 1.7386(19) . ?
S1 C4 1.7438(17) . ?
N1 C4 1.310(2) . ?
N1 C3 1.380(2) . ?
N2 C4 1.353(2) . ?
N2 C5 1.448(2) . ?
N2 H2 0.8600 . ?
C7 C8 1.380(3) 7_655 ?
C7 C6 1.394(3) . ?
C7 H7 0.9300 . ?
C8 C7 1.381(3) 7_655 ?
C8 C6 1.381(3) . ?
C8 H8 0.9300 . ?
C6 C5 1.512(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 C3 1.346(3) . ?
C2 C1 1.503(3) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C4 89.47(9) . . ?
C4 N1 C3 109.79(15) . . ?
C4 N2 C5 122.52(14) . . ?
C4 N2 H2 118.7 . . ?
C5 N2 H2 118.7 . . ?
C8 C7 C6 121.33(18) 7_655 . ?
C8 C7 H7 119.3 7_655 . ?
C6 C7 H7 119.3 . . ?
C7 C8 C6 120.58(18) 7_655 . ?
C7 C8 H8 119.7 7_655 . ?
C6 C8 H8 119.7 . . ?
C8 C6 C7 118.09(16) . . ?
C8 C6 C5 120.81(18) . . ?
C7 C6 C5 121.10(17) . . ?
N2 C5 C6 109.92(15) . . ?
N2 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N2 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C3 C2 C1 129.88(19) . . ?
C3 C2 S1 108.56(13) . . ?
C1 C2 S1 121.55(17) . . ?
C2 C3 N1 117.77(16) . . ?
C2 C3 H3 121.1 . . ?
N1 C3 H3 121.1 . . ?
N1 C4 N2 123.69(15) . . ?
N1 C4 S1 114.39(14) . . ?
N2 C4 S1 121.90(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C7 C8 C6 C7 -0.4(3) 7_655 . . . ?
C7 C8 C6 C5 179.42(17) 7_655 . . . ?
C8 C7 C6 C8 0.4(3) 7_655 . . . ?
C8 C7 C6 C5 -179.42(17) 7_655 . . . ?
C4 N2 C5 C6 -171.56(18) . . . . ?
C8 C6 C5 N2 -121.4(2) . . . . ?
C7 C6 C5 N2 58.4(3) . . . . ?
C4 S1 C2 C3 1.29(15) . . . . ?
C4 S1 C2 C1 -177.98(18) . . . . ?
C1 C2 C3 N1 178.2(2) . . . . ?
S1 C2 C3 N1 -0.9(2) . . . . ?
C4 N1 C3 C2 -0.1(3) . . . . ?
C3 N1 C4 N2 -177.31(18) . . . . ?
C3 N1 C4 S1 1.2(2) . . . . ?
C5 N2 C4 N1 -176.38(19) . . . . ?
C5 N2 C4 S1 5.2(3) . . . . ?
C2 S1 C4 N1 -1.49(16) . . . . ?
C2 S1 C4 N2 177.06(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.23
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1420846'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N4 S2, 2(Br), 2(H2 O)'
_chemical_formula_sum            'C16 H24 Br2 N4 O2 S2'
_chemical_formula_weight         528.31

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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5072(6)
_cell_length_b                   8.4305(7)
_cell_length_c                   9.1386(7)
_cell_angle_alpha                73.216(4)
_cell_angle_beta                 85.375(5)
_cell_angle_gamma                74.943(5)
_cell_volume                     534.72(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3157
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      26.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             266
_exptl_absorpt_coefficient_mu    4.003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_T_max  0.619
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            6700
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1900
_reflns_number_gt                1593
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.5391P] 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         1900
_refine_ls_number_parameters     127
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23771(11) 0.18338(10) 0.52649(8) 0.0419(2) Uani 1 1 d . . .
N1 N 0.2408(3) -0.0888(3) 0.4622(3) 0.0427(6) Uani 1 1 d . . .
H1 H 0.2491 -0.1944 0.4693 0.051 Uiso 1 1 calc R . .
N2 N 0.3348(3) -0.1376(3) 0.7151(3) 0.0422(6) Uani 1 1 d . . .
H2 H 0.3635 -0.2464 0.7285 0.051 Uiso 1 1 calc R . .
C1 C 0.1335(5) 0.3653(4) 0.2212(4) 0.0607(10) Uani 1 1 d . . .
H1A H 0.1003 0.3494 0.1281 0.091 Uiso 1 1 calc R . .
H1B H 0.2384 0.4137 0.2029 0.091 Uiso 1 1 calc R . .
H1C H 0.0317 0.4411 0.2564 0.091 Uiso 1 1 calc R . .
C2 C 0.1803(4) 0.1971(4) 0.3395(3) 0.0429(7) Uani 1 1 d . . .
C3 C 0.1894(4) 0.0418(4) 0.3283(3) 0.0440(7) Uani 1 1 d . . .
H3 H 0.1636 0.0218 0.2383 0.053 Uiso 1 1 calc R . .
C4 C 0.2762(4) -0.0363(4) 0.5786(3) 0.0360(7) Uani 1 1 d . . .
C6 C 0.3529(4) -0.0729(4) 0.8441(3) 0.0414(7) Uani 1 1 d . . .
H6A H 0.3973 0.0300 0.8071 0.050 Uiso 1 1 calc R . .
H6B H 0.4432 -0.1576 0.9149 0.050 Uiso 1 1 calc R . .
C7 C 0.1718(4) -0.0333(4) 0.9269(3) 0.0333(6) Uani 1 1 d . . .
C8 C 0.0995(4) -0.1669(4) 1.0161(3) 0.0397(7) Uani 1 1 d . . .
H8 H 0.1657 -0.2795 1.0276 0.048 Uiso 1 1 calc R . .
C9 C 0.0708(4) 0.1330(4) 0.9121(3) 0.0386(7) Uani 1 1 d . . .
H9 H 0.1176 0.2234 0.8533 0.046 Uiso 1 1 calc R . .
Br1 Br 0.58675(5) 0.56535(4) 0.20261(4) 0.05838(14) Uani 1 1 d . . .
O1 O 0.2458(4) 0.5910(3) 0.4525(4) 0.0627(7) Uani 1 1 d D . .
H1P H 0.334(4) 0.579(5) 0.388(4) 0.080(14) Uiso 1 1 d D . .
H1Q H 0.293(12) 0.530(10) 0.541(5) 0.26(5) Uiso 1 1 d 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 0.0510(5) 0.0380(4) 0.0382(4) -0.0109(3) -0.0020(3) -0.0125(4)
N1 0.0495(15) 0.0405(15) 0.0435(14) -0.0188(12) 0.0049(12) -0.0142(12)
N2 0.0499(15) 0.0336(13) 0.0376(14) -0.0095(11) 0.0043(11) -0.0030(12)
C1 0.074(2) 0.058(2) 0.047(2) -0.0012(17) -0.0131(18) -0.023(2)
C2 0.0416(17) 0.051(2) 0.0368(16) -0.0081(14) -0.0017(13) -0.0168(15)
C3 0.0457(18) 0.057(2) 0.0343(16) -0.0137(14) 0.0013(14) -0.0205(16)
C4 0.0327(15) 0.0384(17) 0.0375(16) -0.0139(13) 0.0073(12) -0.0087(13)
C6 0.0404(16) 0.0472(18) 0.0335(16) -0.0088(13) -0.0021(13) -0.0075(14)
C7 0.0371(15) 0.0372(16) 0.0258(14) -0.0089(12) -0.0010(12) -0.0091(13)
C8 0.0478(18) 0.0301(15) 0.0362(16) -0.0073(12) 0.0005(13) -0.0032(14)
C9 0.0475(18) 0.0368(17) 0.0320(15) -0.0052(12) 0.0032(13) -0.0171(14)
Br1 0.0664(3) 0.0492(2) 0.0558(2) -0.00556(16) -0.00464(17) -0.01699(18)
O1 0.0700(18) 0.0540(16) 0.0670(18) -0.0237(14) -0.0015(15) -0.0121(14)

_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 C4 1.725(3) . ?
S1 C2 1.760(3) . ?
N1 C4 1.333(4) . ?
N1 C3 1.391(4) . ?
N1 H1 0.8600 . ?
N2 C4 1.325(4) . ?
N2 C6 1.462(4) . ?
N2 H2 0.8600 . ?
C1 C2 1.490(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.326(4) . ?
C3 H3 0.9300 . ?
C6 C7 1.509(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C9 1.384(4) . ?
C7 C8 1.394(4) . ?
C8 C9 1.389(4) 2_557 ?
C8 H8 0.9300 . ?
C9 C8 1.389(4) 2_557 ?
C9 H9 0.9300 . ?
O1 H1P 0.861(19) . ?
O1 H1Q 0.87(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
C4 S1 C2 91.19(14) . . ?
C4 N1 C3 114.3(3) . . ?
C4 N1 H1 122.9 . . ?
C3 N1 H1 122.9 . . ?
C4 N2 C6 123.1(2) . . ?
C4 N2 H2 118.5 . . ?
C6 N2 H2 118.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 129.7(3) . . ?
C3 C2 S1 109.5(2) . . ?
C1 C2 S1 120.8(2) . . ?
C2 C3 N1 114.5(3) . . ?
C2 C3 H3 122.7 . . ?
N1 C3 H3 122.7 . . ?
N2 C4 N1 125.2(3) . . ?
N2 C4 S1 124.3(2) . . ?
N1 C4 S1 110.5(2) . . ?
N2 C6 C7 111.8(2) . . ?
N2 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C9 C7 C8 118.6(3) . . ?
C9 C7 C6 121.7(3) . . ?
C8 C7 C6 119.6(3) . . ?
C9 C8 C7 120.5(3) 2_557 . ?
C9 C8 H8 119.8 2_557 . ?
C7 C8 H8 119.8 . . ?
C7 C9 C8 120.9(3) . 2_557 ?
C7 C9 H9 119.6 . . ?
C8 C9 H9 119.6 2_557 . ?
H1P O1 H1Q 105(6) . . ?

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
C4 S1 C2 C3 1.2(2) . . . . ?
C4 S1 C2 C1 -178.0(3) . . . . ?
C1 C2 C3 N1 179.0(3) . . . . ?
S1 C2 C3 N1 -0.2(3) . . . . ?
C4 N1 C3 C2 -1.4(4) . . . . ?
C6 N2 C4 N1 -173.3(3) . . . . ?
C6 N2 C4 S1 7.6(4) . . . . ?
C3 N1 C4 N2 -177.0(3) . . . . ?
C3 N1 C4 S1 2.2(3) . . . . ?
C2 S1 C4 N2 177.3(3) . . . . ?
C2 S1 C4 N1 -1.9(2) . . . . ?
C4 N2 C6 C7 83.3(3) . . . . ?
N2 C6 C7 C9 -105.6(3) . . . . ?
N2 C6 C7 C8 71.7(3) . . . . ?
C9 C7 C8 C9 0.3(5) . . . 2_557 ?
C6 C7 C8 C9 -177.2(3) . . . 2_557 ?
C8 C7 C9 C8 -0.3(5) . . . 2_557 ?
C6 C7 C9 C8 177.1(3) . . . 2_557 ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.398
_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_2
_database_code_depnum_ccdc_archive 'CCDC 1420847'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N4 S2, 2(N O3)'
_chemical_formula_sum            'C16 H20 N6 O6 S2'
_chemical_formula_weight         456.50

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                   7.0178(17)
_cell_length_b                   16.125(4)
_cell_length_c                   9.208(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.814(15)
_cell_angle_gamma                90.00
_cell_volume                     1007.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2455
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      21.75

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            12061
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1812
_reflns_number_gt                1298
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+4.0000P] 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         1812
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.2246(2) 0.38083(8) 0.55342(15) 0.0515(4) Uani 1 1 d . . .
N1 N 0.2324(6) 0.2728(2) 0.3560(4) 0.0441(10) Uani 1 1 d . . .
H1 H 0.2355 0.2494 0.2727 0.053 Uiso 1 1 calc R . .
N2 N 0.2343(7) 0.4111(2) 0.2686(5) 0.0548(12) Uani 1 1 d . . .
H2 H 0.2382 0.4624 0.2950 0.066 Uiso 1 1 calc R . .
C7 C 0.5567(8) 0.4724(3) 0.1469(5) 0.0471(12) Uani 1 1 d . . .
H7 H 0.5955 0.4541 0.2459 0.057 Uiso 1 1 calc R . .
C6 C 0.3712(8) 0.4507(3) 0.0578(5) 0.0429(12) Uani 1 1 d . . .
C8 C 0.3146(8) 0.4788(3) -0.0895(5) 0.0457(12) Uani 1 1 d . . .
H8 H 0.1910 0.4651 -0.1502 0.055 Uiso 1 1 calc R . .
C5 C 0.2335(9) 0.3938(3) 0.1142(5) 0.0531(14) Uani 1 1 d . . .
H5A H 0.1006 0.4003 0.0512 0.064 Uiso 1 1 calc R . .
H5B H 0.2730 0.3367 0.1062 0.064 Uiso 1 1 calc R . .
C4 C 0.2296(7) 0.3550(3) 0.3730(5) 0.0426(11) Uani 1 1 d . . .
C3 C 0.2298(7) 0.2286(3) 0.4852(5) 0.0463(12) Uani 1 1 d . . .
H3 H 0.2311 0.1710 0.4891 0.056 Uiso 1 1 calc R . .
C2 C 0.2254(7) 0.2759(3) 0.6026(5) 0.0460(12) Uani 1 1 d . . .
C1 C 0.2206(8) 0.2514(3) 0.7581(6) 0.0571(14) Uani 1 1 d . . .
H1A H 0.2237 0.1921 0.7663 0.086 Uiso 1 1 calc R . .
H1B H 0.1020 0.2721 0.7790 0.086 Uiso 1 1 calc R . .
H1C H 0.3329 0.2744 0.8290 0.086 Uiso 1 1 calc R . .
O1 O 0.2090(6) 0.1896(2) 0.0863(4) 0.0586(10) Uani 1 1 d . . .
O2 O 0.2154(7) 0.0613(2) 0.0220(4) 0.0748(13) Uani 1 1 d . . .
O3 O 0.3266(6) 0.0964(2) 0.2530(4) 0.0639(11) Uani 1 1 d . . .
N3 N 0.2497(6) 0.1148(2) 0.1201(5) 0.0461(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0748(10) 0.0401(7) 0.0486(8) -0.0053(6) 0.0322(7) -0.0067(6)
N1 0.058(3) 0.033(2) 0.047(2) -0.0024(17) 0.025(2) -0.0036(19)
N2 0.091(4) 0.028(2) 0.054(3) -0.0038(18) 0.037(3) -0.012(2)
C7 0.067(4) 0.036(3) 0.039(3) 0.004(2) 0.015(3) -0.006(2)
C6 0.064(3) 0.028(2) 0.040(3) -0.0045(19) 0.019(2) -0.004(2)
C8 0.058(3) 0.038(3) 0.043(3) -0.002(2) 0.014(2) -0.007(2)
C5 0.079(4) 0.043(3) 0.044(3) -0.003(2) 0.030(3) -0.022(3)
C4 0.049(3) 0.036(3) 0.049(3) -0.004(2) 0.022(2) -0.005(2)
C3 0.055(3) 0.036(3) 0.051(3) 0.008(2) 0.020(3) 0.000(2)
C2 0.050(3) 0.048(3) 0.043(3) 0.003(2) 0.019(2) -0.003(2)
C1 0.066(4) 0.060(3) 0.051(3) 0.008(3) 0.024(3) 0.001(3)
O1 0.091(3) 0.0323(19) 0.054(2) 0.0028(16) 0.021(2) 0.0051(18)
O2 0.114(4) 0.043(2) 0.064(3) -0.0194(19) 0.016(2) -0.001(2)
O3 0.094(3) 0.045(2) 0.049(2) 0.0050(17) 0.011(2) 0.010(2)
N3 0.058(3) 0.031(2) 0.053(3) -0.003(2) 0.021(2) 0.0003(19)

_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 C4 1.721(5) . ?
S1 C2 1.751(5) . ?
N1 C4 1.335(6) . ?
N1 C3 1.391(6) . ?
N1 H1 0.8600 . ?
N2 C4 1.328(6) . ?
N2 C5 1.447(6) . ?
N2 H2 0.8600 . ?
C7 C6 1.395(7) . ?
C7 C8 1.400(7) 3_665 ?
C7 H7 0.9300 . ?
C6 C8 1.388(6) . ?
C6 C5 1.517(6) . ?
C8 C7 1.400(7) 3_665 ?
C8 H8 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 C2 1.331(7) . ?
C3 H3 0.9300 . ?
C2 C1 1.494(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O1 N3 1.261(5) . ?
O2 N3 1.226(5) . ?
O3 N3 1.241(5) . ?

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
C4 S1 C2 90.9(2) . . ?
C4 N1 C3 113.9(4) . . ?
C4 N1 H1 123.1 . . ?
C3 N1 H1 123.1 . . ?
C4 N2 C5 125.9(4) . . ?
C4 N2 H2 117.1 . . ?
C5 N2 H2 117.1 . . ?
C6 C7 C8 120.9(4) . 3_665 ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 3_665 . ?
C8 C6 C7 118.9(4) . . ?
C8 C6 C5 118.9(5) . . ?
C7 C6 C5 122.0(4) . . ?
C6 C8 C7 120.1(5) . 3_665 ?
C6 C8 H8 119.9 . . ?
C7 C8 H8 119.9 3_665 . ?
N2 C5 C6 112.1(4) . . ?
N2 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C4 N1 126.0(4) . . ?
N2 C4 S1 123.0(4) . . ?
N1 C4 S1 111.0(4) . . ?
C2 C3 N1 114.1(4) . . ?
C2 C3 H3 122.9 . . ?
N1 C3 H3 122.9 . . ?
C3 C2 C1 129.6(5) . . ?
C3 C2 S1 110.1(4) . . ?
C1 C2 S1 120.3(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 N3 O3 120.9(4) . . ?
O2 N3 O1 120.1(4) . . ?
O3 N3 O1 119.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C7 C6 C8 -0.4(8) 3_665 . . . ?
C8 C7 C6 C5 176.4(5) 3_665 . . . ?
C7 C6 C8 C7 0.4(8) . . . 3_665 ?
C5 C6 C8 C7 -176.5(4) . . . 3_665 ?
C4 N2 C5 C6 -140.1(5) . . . . ?
C8 C6 C5 N2 -142.4(5) . . . . ?
C7 C6 C5 N2 40.7(7) . . . . ?
C5 N2 C4 N1 3.3(9) . . . . ?
C5 N2 C4 S1 -178.3(4) . . . . ?
C3 N1 C4 N2 178.9(5) . . . . ?
C3 N1 C4 S1 0.2(6) . . . . ?
C2 S1 C4 N2 -178.9(5) . . . . ?
C2 S1 C4 N1 -0.2(4) . . . . ?
C4 N1 C3 C2 -0.1(7) . . . . ?
N1 C3 C2 C1 179.7(5) . . . . ?
N1 C3 C2 S1 -0.1(6) . . . . ?
C4 S1 C2 C3 0.2(4) . . . . ?
C4 S1 C2 C1 -179.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1420848'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N4 S2, 2(H2 O4 P), 2(H3 O4 P)'
_chemical_formula_sum            'C16 H30 N4 O16 P4 S2'
_chemical_formula_weight         722.44

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'
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'
P P 0.1023 0.0942 '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'
H H 0.0000 0.0000 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.0722(8)
_cell_length_b                   19.8911(19)
_cell_length_c                   9.3871(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.293(4)
_cell_angle_gamma                90.00
_cell_volume                     1491.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            13418
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2691
_reflns_number_gt                2473
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
DFIX 0.85 0.02 O2 H5P
DFIX 0.85 0.02 O20 H4P
DFIX 0.86 0.02 O5 H5P
DFIX 0.85 0.02 H5P O5
DFIX 1.54 0.02 H5X O5
DFIX 0.85 0.02 O5 H5P
DFIX 0.93 0.02 H5P O5
DFIX 0.86 0.02 H2P O2  H3P O3  O5 H5Q  O8 H8P  O7 H7P
DFIX 0.86 0.02 O2 H2P  O3 H3P  O5 H5Q  O8 H8P  O7 H7P
DFIX 0.86 0.02 O2 H2P  O3 H3P  O8 H8P  O7 H7P  O5 H5Q
;

_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)+(0.0000P)²+2.3000P] 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         2691
_refine_ls_number_parameters     211
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25925(10) -0.02432(3) 0.39158(7) 0.04848(19) Uani 1 1 d . . .
N2 N 0.3385(3) 0.08597(11) 0.2483(2) 0.0499(6) Uani 1 1 d . . .
H2 H 0.3636 0.1280 0.2462 0.060 Uiso 1 1 calc R . .
N1 N 0.3038(3) 0.09309(11) 0.4922(2) 0.0473(6) Uani 1 1 d . . .
H1 H 0.3244 0.1354 0.5004 0.057 Uiso 1 1 calc R . .
C6 C 0.1613(4) 0.02226(12) 0.0557(3) 0.0429(6) Uani 1 1 d . . .
C7 C 0.0335(4) 0.06789(13) 0.0167(3) 0.0486(7) Uani 1 1 d . . .
H7 H 0.0550 0.1137 0.0274 0.058 Uiso 1 1 calc R . .
C8 C 0.1252(4) -0.04638(13) 0.0380(3) 0.0492(7) Uani 1 1 d . . .
H8 H 0.2095 -0.0778 0.0634 0.059 Uiso 1 1 calc R . .
C5 C 0.3348(4) 0.04620(14) 0.1164(3) 0.0518(7) Uani 1 1 d . . .
H5A H 0.4074 0.0075 0.1366 0.062 Uiso 1 1 calc R . .
H5B H 0.3788 0.0732 0.0444 0.062 Uiso 1 1 calc R . .
C4 C 0.3048(3) 0.05975(12) 0.3704(3) 0.0413(6) Uani 1 1 d . . .
C3 C 0.2667(4) 0.05396(15) 0.6056(3) 0.0541(7) Uani 1 1 d . . .
H3 H 0.2604 0.0714 0.6966 0.065 Uiso 1 1 calc R . .
C2 C 0.2406(4) -0.01109(14) 0.5727(3) 0.0501(7) Uani 1 1 d . . .
C1 C 0.1967(5) -0.06911(17) 0.6628(3) 0.0722(10) Uani 1 1 d . . .
H1A H 0.1939 -0.0541 0.7596 0.108 Uiso 1 1 calc R . .
H1B H 0.2794 -0.1038 0.6630 0.108 Uiso 1 1 calc R . .
H1C H 0.0889 -0.0865 0.6233 0.108 Uiso 1 1 calc R . .
P1 P 0.44525(7) 0.26911(3) 0.37877(5) 0.02378(13) Uani 1 1 d . . .
O1 O 0.61016(19) 0.30599(8) 0.40071(16) 0.0338(4) Uani 1 1 d . . .
O2 O 0.3073(2) 0.32508(8) 0.35338(18) 0.0358(4) Uani 1 1 d D . .
O3 O 0.4271(2) 0.22289(8) 0.24451(16) 0.0357(4) Uani 1 1 d D . .
O4 O 0.4154(2) 0.22442(8) 0.50384(15) 0.0317(4) Uani 1 1 d . . .
P2 P 0.90803(7) 0.27046(3) 0.17404(6) 0.02840(14) Uani 1 1 d . . .
O6 O 1.0189(2) 0.26286(10) 0.31484(16) 0.0417(4) Uani 1 1 d . . .
O8 O 0.8302(2) 0.20161(8) 0.12634(18) 0.0369(4) Uani 1 1 d D . .
O7 O 1.0069(2) 0.29880(10) 0.05752(19) 0.0460(5) Uani 1 1 d D . .
O5 O 0.7688(2) 0.32326(8) 0.18074(19) 0.0376(4) Uani 1 1 d D . .
H8P H 0.753(3) 0.1994(16) 0.053(2) 0.064(10) Uiso 1 1 d D . .
H2P H 0.209(2) 0.3095(14) 0.338(3) 0.062(10) Uiso 1 1 d D . .
H7P H 1.004(4) 0.2800(15) -0.024(2) 0.073(11) Uiso 1 1 d D . .
H3P H 0.419(5) 0.2413(18) 0.161(2) 0.103(14) Uiso 1 1 d D . .
H5Q H 0.713(3) 0.3202(16) 0.251(2) 0.066(10) Uiso 1 1 d 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 0.0775(5) 0.0279(3) 0.0412(4) -0.0022(3) 0.0125(3) -0.0115(3)
N2 0.0732(17) 0.0281(11) 0.0489(13) 0.0027(10) 0.0103(12) -0.0107(11)
N1 0.0641(15) 0.0292(11) 0.0473(13) -0.0082(10) 0.0039(11) -0.0066(10)
C6 0.0683(18) 0.0329(13) 0.0294(12) 0.0013(10) 0.0141(12) 0.0044(12)
C7 0.079(2) 0.0241(12) 0.0448(15) 0.0001(11) 0.0142(14) 0.0044(13)
C8 0.075(2) 0.0305(13) 0.0428(15) 0.0028(11) 0.0100(14) 0.0117(13)
C5 0.074(2) 0.0404(15) 0.0441(15) 0.0046(12) 0.0187(14) 0.0013(14)
C4 0.0497(16) 0.0278(12) 0.0458(15) -0.0021(11) 0.0048(12) -0.0046(11)
C3 0.071(2) 0.0513(17) 0.0396(15) -0.0086(13) 0.0067(14) -0.0083(15)
C2 0.0651(19) 0.0467(16) 0.0386(14) -0.0007(12) 0.0083(13) -0.0111(14)
C1 0.104(3) 0.067(2) 0.0468(18) 0.0081(15) 0.0154(18) -0.027(2)
P1 0.0267(3) 0.0256(3) 0.0187(3) 0.0003(2) 0.0022(2) -0.0018(2)
O1 0.0271(8) 0.0398(9) 0.0339(9) 0.0031(7) 0.0022(7) -0.0051(7)
O2 0.0278(9) 0.0326(9) 0.0456(10) 0.0010(7) 0.0003(7) 0.0020(7)
O3 0.0596(11) 0.0285(8) 0.0194(8) -0.0003(6) 0.0074(7) -0.0044(7)
O4 0.0441(9) 0.0326(8) 0.0187(7) 0.0008(6) 0.0049(6) -0.0062(7)
P2 0.0257(3) 0.0355(3) 0.0238(3) -0.0005(2) 0.0031(2) -0.0031(2)
O6 0.0287(9) 0.0684(12) 0.0268(8) 0.0032(8) -0.0004(7) -0.0072(8)
O8 0.0403(10) 0.0299(8) 0.0377(9) -0.0004(7) -0.0034(8) 0.0013(7)
O7 0.0499(11) 0.0598(12) 0.0310(9) -0.0041(8) 0.0156(8) -0.0156(9)
O5 0.0399(10) 0.0326(9) 0.0413(10) 0.0013(7) 0.0095(8) 0.0023(7)

_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 C4 1.730(2) . ?
S1 C2 1.749(3) . ?
N2 C4 1.323(3) . ?
N2 C5 1.466(3) . ?
N2 H2 0.8600 . ?
N1 C4 1.323(3) . ?
N1 C3 1.385(4) . ?
N1 H1 0.8600 . ?
C6 C7 1.383(4) . ?
C6 C8 1.401(4) . ?
C6 C5 1.510(4) . ?
C7 C8 1.378(4) 3 ?
C7 H7 0.9300 . ?
C8 C7 1.378(4) 3 ?
C8 H8 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 C2 1.340(4) . ?
C3 H3 0.9300 . ?
C2 C1 1.503(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
P1 O1 1.5079(16) . ?
P1 O4 1.5193(15) . ?
P1 O3 1.5497(16) . ?
P1 O2 1.5685(16) . ?
O2 H2P 0.844(11) . ?
O3 H3P 0.862(11) . ?
P2 O6 1.4931(16) . ?
P2 O8 1.5457(17) . ?
P2 O5 1.5463(18) . ?
P2 O7 1.5503(18) . ?
O8 H8P 0.859(11) . ?
O7 H7P 0.847(11) . ?
O5 H5Q 0.852(11) . ?

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
C4 S1 C2 90.91(13) . . ?
C4 N2 C5 122.5(2) . . ?
C4 N2 H2 118.8 . . ?
C5 N2 H2 118.8 . . ?
C4 N1 C3 114.3(2) . . ?
C4 N1 H1 122.9 . . ?
C3 N1 H1 122.9 . . ?
C7 C6 C8 118.3(3) . . ?
C7 C6 C5 120.6(2) . . ?
C8 C6 C5 121.2(3) . . ?
C8 C7 C6 120.9(2) 3 . ?
C8 C7 H7 119.6 3 . ?
C6 C7 H7 119.6 . . ?
C7 C8 C6 120.9(3) 3 . ?
C7 C8 H8 119.6 3 . ?
C6 C8 H8 119.6 . . ?
N2 C5 C6 113.2(2) . . ?
N2 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
N2 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
N2 C4 N1 125.4(2) . . ?
N2 C4 S1 123.69(19) . . ?
N1 C4 S1 110.91(19) . . ?
C2 C3 N1 114.2(2) . . ?
C2 C3 H3 122.9 . . ?
N1 C3 H3 122.9 . . ?
C3 C2 C1 130.9(3) . . ?
C3 C2 S1 109.7(2) . . ?
C1 C2 S1 119.4(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 P1 O4 114.48(9) . . ?
O1 P1 O3 112.21(10) . . ?
O4 P1 O3 105.92(8) . . ?
O1 P1 O2 105.60(9) . . ?
O4 P1 O2 110.14(9) . . ?
O3 P1 O2 108.40(9) . . ?
P1 O2 H2P 113(2) . . ?
P1 O3 H3P 118(3) . . ?
O6 P2 O8 109.47(10) . . ?
O6 P2 O5 112.28(10) . . ?
O8 P2 O5 110.26(10) . . ?
O6 P2 O7 110.95(10) . . ?
O8 P2 O7 110.30(10) . . ?
O5 P2 O7 103.47(11) . . ?
P2 O8 H8P 120(2) . . ?
P2 O7 H7P 122(2) . . ?
P2 O5 H5Q 117(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
C8 C6 C7 C8 0.1(4) . . . 3 ?
C5 C6 C7 C8 -179.6(2) . . . 3 ?
C7 C6 C8 C7 -0.1(4) . . . 3 ?
C5 C6 C8 C7 179.6(2) . . . 3 ?
C4 N2 C5 C6 66.9(3) . . . . ?
C7 C6 C5 N2 59.1(3) . . . . ?
C8 C6 C5 N2 -120.7(3) . . . . ?
C5 N2 C4 N1 -179.0(3) . . . . ?
C5 N2 C4 S1 2.2(4) . . . . ?
C3 N1 C4 N2 -179.2(3) . . . . ?
C3 N1 C4 S1 -0.3(3) . . . . ?
C2 S1 C4 N2 178.7(3) . . . . ?
C2 S1 C4 N1 -0.3(2) . . . . ?
C4 N1 C3 C2 0.9(4) . . . . ?
N1 C3 C2 C1 -179.5(3) . . . . ?
N1 C3 C2 S1 -1.1(4) . . . . ?
C4 S1 C2 C3 0.8(3) . . . . ?
C4 S1 C2 C1 179.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.060
