# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_shrv257

_audit_creation_date             2014-02-14
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
; 
 (E)-3,3'-(diazene-1,2-diyl)bis(1,2,4-oxadiazol-5-amine) DMSO hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N8 O2, C2 H6 O1 S1, H2 O1'
_chemical_formula_sum            'C6 H12 N8 O4 S'
_chemical_formula_weight         292.30

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   P2(1)/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                   7.4439(8)
_cell_length_b                   22.253(3)
_cell_length_c                   7.6787(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.7710(10)
_cell_angle_gamma                90.00
_cell_volume                     1260.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9022
_exptl_absorpt_correction_T_max  0.9506

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11449
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.47
_reflns_number_total             2613
_reflns_number_gt                2413
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_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)+(0.0394P)²+0.4554P] 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         2613
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O1 O 0.56832(12) -0.11579(4) 0.17227(11) 0.0224(2) Uani 1 1 d . . .
N2 N 0.58605(15) -0.09860(5) 0.35283(13) 0.0234(2) Uani 1 1 d . . .
C3 C 0.66634(15) -0.04640(5) 0.34983(15) 0.0183(2) Uani 1 1 d . . .
N4 N 0.70411(13) -0.02601(5) 0.19216(13) 0.0188(2) Uani 1 1 d . . .
C5 C 0.64140(15) -0.07029(5) 0.08637(16) 0.0186(2) Uani 1 1 d . . .
N6 N 0.70989(13) -0.01708(5) 0.51336(13) 0.0195(2) Uani 1 1 d . . .
N7 N 0.80070(13) 0.03005(5) 0.49832(13) 0.0188(2) Uani 1 1 d . . .
C8 C 0.84718(15) 0.05879(6) 0.66258(15) 0.0179(2) Uani 1 1 d . . .
N9 N 0.94357(14) 0.10800(5) 0.66236(13) 0.0210(2) Uani 1 1 d . . .
O10 O 0.96817(11) 0.12419(4) 0.84353(10) 0.0211(2) Uani 1 1 d . . .
C11 C 0.88185(16) 0.08115(5) 0.92746(15) 0.0183(2) Uani 1 1 d . . .
N12 N 0.80443(14) 0.03964(5) 0.81952(13) 0.0192(2) Uani 1 1 d . . .
N13 N 0.64307(15) -0.07532(5) -0.08371(13) 0.0233(2) Uani 1 1 d . . .
H13A H 0.6907 -0.0466 -0.1417 0.028 Uiso 1 1 calc R . .
H13B H 0.5965 -0.1074 -0.1398 0.028 Uiso 1 1 calc R . .
N14 N 0.88198(15) 0.08579(5) 1.09795(13) 0.0233(2) Uani 1 1 d . . .
H14A H 0.8250 0.0589 1.1542 0.028 Uiso 1 1 calc R . .
H14B H 0.9391 0.1158 1.1560 0.028 Uiso 1 1 calc R . .
S1S S 0.64090(4) 0.186655(13) 1.34282(4) 0.02096(10) Uani 1 1 d . . .
O2S O 0.44212(12) 0.18289(4) 1.26785(12) 0.0258(2) Uani 1 1 d . . .
C3S C 0.7296(2) 0.24430(7) 1.2177(2) 0.0377(4) Uani 1 1 d . . .
H3SA H 0.7274 0.2308 1.0960 0.057 Uiso 1 1 calc R . .
H3SB H 0.8548 0.2532 1.2684 0.057 Uiso 1 1 calc R . .
H3SC H 0.6555 0.2806 1.2200 0.057 Uiso 1 1 calc R . .
C4S C 0.64966(19) 0.22691(7) 1.54350(18) 0.0312(3) Uani 1 1 d . . .
H4SC H 0.5797 0.2642 1.5234 0.047 Uiso 1 1 calc R . .
H4SD H 0.7760 0.2366 1.5878 0.047 Uiso 1 1 calc R . .
H4SE H 0.5981 0.2022 1.6300 0.047 Uiso 1 1 calc R . .
O5S O 0.09053(13) 0.16407(5) 1.34697(12) 0.0261(2) Uani 1 1 d . . .
H5SA H 0.200(3) 0.1683(8) 1.344(2) 0.039 Uiso 1 1 d . . .
H5SB H 0.081(2) 0.1491(8) 1.444(2) 0.039 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
O1 0.0283(5) 0.0199(4) 0.0190(4) -0.0009(3) 0.0036(3) -0.0058(3)
N2 0.0287(5) 0.0235(6) 0.0180(5) -0.0007(4) 0.0038(4) -0.0039(4)
C3 0.0180(5) 0.0189(6) 0.0182(6) 0.0003(4) 0.0028(4) 0.0008(4)
N4 0.0214(5) 0.0185(5) 0.0167(5) -0.0003(4) 0.0027(4) -0.0011(4)
C5 0.0177(5) 0.0166(6) 0.0212(6) 0.0010(4) 0.0018(4) -0.0004(4)
N6 0.0202(5) 0.0198(5) 0.0187(5) 0.0001(4) 0.0031(4) 0.0000(4)
N7 0.0195(5) 0.0199(5) 0.0171(5) 0.0005(4) 0.0025(4) 0.0003(4)
C8 0.0177(5) 0.0186(6) 0.0175(6) 0.0009(4) 0.0027(4) 0.0012(4)
N9 0.0247(5) 0.0232(6) 0.0150(5) 0.0001(4) 0.0022(4) -0.0023(4)
O10 0.0260(4) 0.0205(4) 0.0167(4) -0.0002(3) 0.0025(3) -0.0051(3)
C11 0.0186(5) 0.0172(6) 0.0192(6) 0.0019(4) 0.0030(4) -0.0003(4)
N12 0.0222(5) 0.0193(5) 0.0160(5) -0.0001(4) 0.0029(4) -0.0022(4)
N13 0.0314(6) 0.0202(5) 0.0180(5) -0.0018(4) 0.0027(4) -0.0066(4)
N14 0.0304(6) 0.0223(5) 0.0174(5) -0.0019(4) 0.0042(4) -0.0078(4)
S1S 0.02032(17) 0.01821(17) 0.02397(17) -0.00147(11) 0.00157(12) 0.00220(11)
O2S 0.0226(5) 0.0260(5) 0.0272(5) -0.0014(4) -0.0024(4) -0.0042(3)
C3S 0.0284(7) 0.0409(9) 0.0459(9) 0.0125(7) 0.0122(6) -0.0018(6)
C4S 0.0310(7) 0.0306(7) 0.0310(7) -0.0098(6) 0.0002(5) -0.0036(6)
O5S 0.0238(5) 0.0327(5) 0.0215(5) 0.0013(4) 0.0019(4) -0.0031(4)

_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
O1 C5 1.3612(14) . ?
O1 N2 1.4270(13) . ?
N2 C3 1.3080(16) . ?
C3 N4 1.3576(15) . ?
C3 N6 1.4133(15) . ?
N4 C5 1.3214(16) . ?
C5 N13 1.3125(16) . ?
N6 N7 1.2614(15) . ?
N7 C8 1.4149(15) . ?
C8 N9 1.3092(16) . ?
C8 N12 1.3561(15) . ?
N9 O10 1.4246(12) . ?
O10 C11 1.3630(14) . ?
C11 N14 1.3131(15) . ?
C11 N12 1.3203(16) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
S1S O2S 1.5158(9) . ?
S1S C4S 1.7760(14) . ?
S1S C3S 1.7821(15) . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?
C4S H4SC 0.9800 . ?
C4S H4SD 0.9800 . ?
C4S H4SE 0.9800 . ?
O5S H5SA 0.821(19) . ?
O5S H5SB 0.830(19) . ?

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
C5 O1 N2 106.32(9) . . ?
C3 N2 O1 101.73(9) . . ?
N2 C3 N4 117.57(11) . . ?
N2 C3 N6 116.42(10) . . ?
N4 C3 N6 125.99(11) . . ?
C5 N4 C3 101.56(10) . . ?
N13 C5 N4 128.69(11) . . ?
N13 C5 O1 118.48(10) . . ?
N4 C5 O1 112.82(10) . . ?
N7 N6 C3 111.34(10) . . ?
N6 N7 C8 111.33(10) . . ?
N9 C8 N12 117.29(10) . . ?
N9 C8 N7 116.42(10) . . ?
N12 C8 N7 126.27(11) . . ?
C8 N9 O10 102.03(9) . . ?
C11 O10 N9 106.11(9) . . ?
N14 C11 N12 128.49(11) . . ?
N14 C11 O10 118.64(11) . . ?
N12 C11 O10 112.86(10) . . ?
C11 N12 C8 101.71(10) . . ?
C5 N13 H13A 120.0 . . ?
C5 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C11 N14 H14A 120.0 . . ?
C11 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
O2S S1S C4S 106.07(6) . . ?
O2S S1S C3S 104.42(6) . . ?
C4S S1S C3S 97.57(8) . . ?
S1S C3S H3SA 109.5 . . ?
S1S C3S H3SB 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
S1S C3S H3SC 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
S1S C4S H4SC 109.5 . . ?
S1S C4S H4SD 109.5 . . ?
H4SC C4S H4SD 109.5 . . ?
S1S C4S H4SE 109.5 . . ?
H4SC C4S H4SE 109.5 . . ?
H4SD C4S H4SE 109.5 . . ?
H5SA O5S H5SB 106.0(16) . . ?

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
C5 O1 N2 C3 -0.25(12) . . . . ?
O1 N2 C3 N4 0.34(14) . . . . ?
O1 N2 C3 N6 -178.12(9) . . . . ?
N2 C3 N4 C5 -0.28(14) . . . . ?
N6 C3 N4 C5 178.01(11) . . . . ?
C3 N4 C5 N13 -179.28(12) . . . . ?
C3 N4 C5 O1 0.08(13) . . . . ?
N2 O1 C5 N13 179.54(10) . . . . ?
N2 O1 C5 N4 0.11(13) . . . . ?
N2 C3 N6 N7 174.16(10) . . . . ?
N4 C3 N6 N7 -4.15(16) . . . . ?
C3 N6 N7 C8 -178.90(9) . . . . ?
N6 N7 C8 N9 179.28(10) . . . . ?
N6 N7 C8 N12 0.62(16) . . . . ?
N12 C8 N9 O10 -0.27(14) . . . . ?
N7 C8 N9 O10 -179.06(9) . . . . ?
C8 N9 O10 C11 0.35(11) . . . . ?
N9 O10 C11 N14 -179.22(10) . . . . ?
N9 O10 C11 N12 -0.34(13) . . . . ?
N14 C11 N12 C8 178.91(12) . . . . ?
O10 C11 N12 C8 0.17(13) . . . . ?
N9 C8 N12 C11 0.08(14) . . . . ?
N7 C8 N12 C11 178.73(11) . . . . ?

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
N13 H13A N12 0.88 2.13 2.9631(15) 156.6 1_554
N13 H13B O2S 0.88 1.95 2.8087(14) 165.4 3_656
N14 H14A N4 0.88 2.13 2.9538(15) 155.7 1_556
N14 H14B O5S 0.88 2.03 2.8806(14) 161.8 1_655
O5S H5SA O2S 0.821(19) 1.998(19) 2.7971(14) 164.2(17) .
O5S H5SB N9 0.830(19) 2.269(19) 3.0554(14) 158.3(16) 1_456

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 1015568'
