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In the title disulfide, C12H8N6O2S2, all bond lengths and angles are within normal ranges, and the mol­ecules are linked into centrosymmetric R22(20) dimers by simple C-H...N inter­actions. Weak inter­molecular C-H...[pi](arene) and [pi]-[pi] inter­actions, involving the benzene CH groups and the benzene rings, and the pyridine rings, respectively, further stabilize and reinforce the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010704142X/sf3052sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010704142X/sf3052Isup2.hkl
Contains datablock I

CCDC reference: 665529

Comment top

This paper forms part of our continuing study of the synthesis and structural characterization of divalent sulfur compounds (Brito et al., 2006, and references therein). We are particularly interested in the synthesis of unsymmetrical disulfides as flexible ligands, and in their binding modes, for the fabrication of different coordination polymer topologies.

The molecular structure of the title compound, (I) is shown in Fig. 1, and selected geometric parameters are given in Table 1. Yellow crystals of (I) were obtained from the rhodium(I) complex-catalysed reaction of 5,5'-dinitro-2,2'-dithiodipyridine with 5,5-dithiobis(1-phenyl-1H-tetrazole). The molecule consists of a 5-nitropyridine ring and a 1-phenyl-1H-tetrazole ring linked by a bridging disulfide group.

A search of the Cambridge Structural Database (CSD, Version 5.28 of May 2007; Allen, 2002) did not find any disulfide compounds with the 1-pheny-1H-tetrazole fragment. The 5-nitropyridine fragment of (I) shows excellent agreement with the bonding geometries of previously reported structures (Brito, Mundaca et al., 2007). The nitro group is rotated by about −12.3 (4)° out the plane of the pyridine ring. In the strongly electronegative 1-phenyltetrazole system, the tetrazole ring is planar, with a mean deviation from the least-squares plane of 0.0036 (17) Å. The dihedral angle between the least-squares planes of the tetrazole and benzene rings is 55.17 (11)°. The tetrazole ring geometry found in (I), with the S substituent at C5, is normal for 1,5-disubstituted tetrazoles with alkyl or aryl substituents (Allen, 2002), as are all other geometric parameters, which fall within the expected ranges.

The gross structure adopted by compound (I) is essentially the same as those reported previously for precursor products, namely 5,5'-dinitro-2,2'-dithiodipyridine (Brito, Mundaca et al., 2007) and 5,5'-dithiobis(1-phenyl-1H-tetrazole) (Brito, Cárdenas et al., 2007). The larger observed differences between (I) and 5,5'-dinitro-2,2'-dithiodipyridine are only in the N—C—S and C—C—S bond angles, [109.64 (18) and 125.8 (2), and 120.02 (2) and 116.0 (2)°, respectively]. A database survey of C—S—S—C fragments (Allen et al., 1987) found that S—S bond distances are bimodally distributed: for torsion angles in the ranges 75–105° and 0–20°, the mean S—S bond distances are 2.031 (15) and 2.070 (22) Å, respectively. The corresponding value in the title compound is 2.0427 (10) Å, placing it in the lower quartile for Allen's first set. The N1—C1 bond length is 1.441 (3) Å, which is almost the same as a normal NC(phenyl) single bond. These facts indicate that conjugation affects between the phenyl and tetrazole rings in (I) are negligible (Lyakhov et al., 2006). The C—S bond lengths differ by 0.019 Å and this, coupled with the apparent lack of S—S double-bond character, shows that there is probably no communication between the two ring systems via the disulfide bridge, despite having a π donor at one end and a π acceptor at the other. Using a bond length–bond order relationship (Pauling, 1960; Bürgi & Dunitz, 1987), it can be shown that the C—S bonds in compound (I) have partial double-bond character of 12% (1.78 Å) and 20% (1.76 Å), respectively. The latter value is different from that found in, say, 5,5'-dithiobis(1-phenyl-1H-tetrazole) (Brito, Mundaca et al., 2007), where the sulfide linkage has about 35% double-bond character. The relationship between bond order (n) and bond length (rn) for sulfur compounds (rn = rl − 0.27ln n) has been derived from the following standard (rl) bond lengths: C—S (single bond, n = 1) = 1.81 Å (dimethyl sulfide, ethyl methyl sulfide; Lide, 1993), C—S (double bond, n = 2) = 1.61 Å (thioformaldehyde; Lide, 1993) and C—S (triple bond, n = 3) = 1.54 Å (carbon monosulfide; Bell et al., 1972).

The molecular conformations are dominated by the near orthogonality of the lone pairs on the two adjacent S atoms (Glidewell et al., 2000). Furthermore, a short intramolecular C9—H9···S1 contact (Table 2), may stabilize the conformation adopted by the molecule in the solid state (Fig. 1). The molecules are linked into centrosymmetric R22(20) dimers centred at (1/2, 1/2, 1/2) by simple C—H···N interactions (Bernstein et al., 1995). Aromatic atom C3 at (x, y, z) acts as a hydrogen-bond donor to atom N5 at (−x + 1, −y + 1, −z + 1) (Fig. 2).

The crystal structure is further stabilized and reinforced by weak intermolecular C—H···π(arene) interactions, involving the benzene C—H groups and the benzene rings (Fig. 3 and Table 2), and by ππ interactions (Fig. 3). The ππ interactions occur between pyridine rings at (x, y, z) and (−x + 1, −y + 1/2, z), with a centroid-to- centroid distance of 3.894 (4) Å and a dihedral angle between the ring planes of 0.02 (1)°; these values are ideal for the development of this type of interaction.

Experimental top

All reactions were carried out under an atmosphere of purified nitrogen. Solvents used were dried and distilled prior to use. The title compound was obtained as yellow block crystals using the method described by Tanaka & Ajiki (2004). Into a 20 ml three-necked flask equipped with an overhead stirrer was placed 5,5'-dithiobis(1-phenyl-1H-tetrazole) (177.2 mg, 4 mmol) and 4-nitrophenyldisulfide (38.54 mg, 1 mmol) in CH2Cl2 (5 ml). Once the components were mixed, bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, [Rh(cod)2]BF4 (6 mg, 0.03 mmol), was added and the resulting mixture stirred for 3 h at room temperature. The resulting solution was kept at 298 K for 1.5 h under air. The solution was concentrated and purified by silica-gel chromatography (hexane–EtOAc = 20:1 v/v). Yellow block crystals of (I) suitable for X-ray analysis were grown from a solution in hexane–EtOAc (1:1 v/v) at 298 K over a period of a few days in air. Analysis: m.p. 393–394 K; FT– IR (KBr pellet, cm−1): ν(s, C—H) 3066, ν(s, C—H monosubstitution) 766, ν(s, CC) 1384, ν(s, CC) 1593, ν(m, CN) 1524, ν(w, C—S) 740, ν[s, NO of NO2 (symmetric)] 1345, ν[s, NO of NO2 (asymmetric)] 1566, ν(w, S—S) 555.

Refinement top

All H atoms were located in a difference map and their positional and isotropic displacement parameters were refined freely. [C—H = 0.86 (3)–0.99 (3) Å]. 67 reflections were not included in the data set as they were either partially obscured by the beam stop or were eliminated during data reduction.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The intramolecular hydrogen bond is indicated by a double-dashed line.
[Figure 2] Fig. 2. A fragment of the structure of (I), viewed along the a axis. Dashed lines show C—H···N interactions. Only H atoms participating in hydrogen bonding are shown. [Symmetry code: (i) −x + 1, −y + 1, −z + 1].
[Figure 3] Fig. 3. The crystal structure of (I), viewed along the a axis. Dashed lines show C—H···Cg1 and Cg2···Cg2 interactions. Only H atoms participating in hydrogen bonding are shown. Cg1 and Cg2 are the centroids of the rings defined by atoms C1–C6 and N5/C8–C12, respectively. [Symmetry codes: (iii) x − 1/2, −y + 3/2, z; (iv) −x, −y + 1, −z].
5-(5-Nitropyridin-2-yldithio)-1-phenyl-1H-tetrazole top
Crystal data top
C12H8N6O2S2F(000) = 680
Mr = 332.36Dx = 1.601 Mg m3
Monoclinic, P21/aMelting point = 393–394 K
Hall symbol: -P 2yabMo Kα radiation, λ = 0.71073 Å
a = 7.4161 (2) ÅCell parameters from 9419 reflections
b = 21.6740 (6) Åθ = 2.4–27.5°
c = 9.0312 (3) ŵ = 0.40 mm1
β = 108.233 (6)°T = 295 K
V = 1378.76 (7) Å3Block, yellow
Z = 40.22 × 0.20 × 0.15 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3104 independent reflections
Radiation source: fine-focus sealed tube2656 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 99
Tmin = 0.910, Tmax = 0.943k = 2528
9028 measured reflectionsl = 118
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.056P)2 + 0.8023P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139(Δ/σ)max = 0.021
S = 1.16Δρmax = 0.34 e Å3
3104 reflectionsΔρmin = 0.26 e Å3
231 parameters
Crystal data top
C12H8N6O2S2V = 1378.76 (7) Å3
Mr = 332.36Z = 4
Monoclinic, P21/aMo Kα radiation
a = 7.4161 (2) ŵ = 0.40 mm1
b = 21.6740 (6) ÅT = 295 K
c = 9.0312 (3) Å0.22 × 0.20 × 0.15 mm
β = 108.233 (6)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
3104 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
2656 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.943Rint = 0.054
9028 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.139All H-atom parameters refined
S = 1.16Δρmax = 0.34 e Å3
3104 reflectionsΔρmin = 0.26 e Å3
231 parameters
Special details top

Experimental. IR spectroscopy performed with a Thermo Nicolet Avatar 330 spectrometer.

Melting points were determined using an electro thermal melting point detection apparatus TG-DSC Mettler Toledo.

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

Refinement. 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 > σ(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. There are no solvent molecules present and there is no disorder. All non-hydrogen atoms were refined anisotropically. The coordinates and U(iso) values for the hydrogen atoms were freely refined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.41164 (9)0.66766 (3)0.27264 (8)0.0411 (2)
S20.42461 (9)0.57611 (3)0.22318 (7)0.0410 (2)
O10.2424 (4)0.54863 (15)0.4551 (3)0.0801 (8)
O20.1135 (4)0.45827 (12)0.4252 (3)0.0643 (7)
N10.1820 (3)0.67965 (9)0.4621 (2)0.0279 (4)
N20.0045 (3)0.68553 (11)0.4463 (2)0.0370 (5)
N30.0952 (3)0.68203 (12)0.2983 (3)0.0432 (6)
N40.0271 (3)0.67471 (11)0.2149 (2)0.0403 (5)
N50.2520 (3)0.50604 (10)0.0048 (3)0.0417 (5)
N60.1230 (4)0.51153 (13)0.3850 (3)0.0492 (6)
C10.3200 (3)0.67998 (11)0.6153 (2)0.0265 (5)
C20.4414 (4)0.63069 (13)0.6632 (3)0.0358 (6)
C30.5655 (4)0.63095 (15)0.8136 (3)0.0444 (7)
C40.5656 (4)0.67993 (16)0.9122 (3)0.0453 (7)
C50.4430 (4)0.72875 (14)0.8630 (3)0.0400 (6)
C60.3182 (3)0.72941 (13)0.7115 (3)0.0328 (5)
C70.1981 (3)0.67277 (11)0.3181 (3)0.0310 (5)
C80.2624 (3)0.56573 (12)0.0327 (3)0.0309 (5)
C90.1584 (4)0.61202 (12)0.0628 (3)0.0331 (5)
C100.0317 (4)0.59435 (13)0.2035 (3)0.0349 (6)
C110.0185 (3)0.53267 (13)0.2408 (3)0.0356 (6)
C120.1311 (4)0.49009 (14)0.1427 (4)0.0443 (7)
H20.442 (4)0.5990 (14)0.606 (3)0.033 (7)*
H30.647 (5)0.5982 (17)0.857 (4)0.058 (9)*
H40.644 (4)0.6795 (14)1.007 (4)0.046 (8)*
H50.445 (4)0.7619 (15)0.938 (4)0.048 (8)*
H60.237 (4)0.7605 (13)0.679 (3)0.032 (7)*
H90.168 (4)0.6540 (14)0.033 (3)0.042 (8)*
H100.046 (5)0.6227 (16)0.267 (4)0.052 (9)*
H120.126 (5)0.4497 (19)0.156 (4)0.067 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0413 (4)0.0501 (4)0.0355 (4)0.0108 (3)0.0173 (3)0.0122 (3)
S20.0416 (4)0.0490 (5)0.0300 (3)0.0095 (3)0.0080 (3)0.0000 (3)
O10.0594 (15)0.106 (2)0.0558 (15)0.0161 (15)0.0098 (12)0.0153 (15)
O20.0794 (16)0.0598 (16)0.0556 (14)0.0283 (12)0.0240 (12)0.0243 (12)
N10.0284 (9)0.0302 (11)0.0229 (10)0.0024 (8)0.0050 (7)0.0032 (8)
N20.0296 (10)0.0452 (13)0.0338 (11)0.0055 (9)0.0064 (8)0.0055 (10)
N30.0347 (11)0.0555 (15)0.0323 (12)0.0059 (10)0.0001 (9)0.0045 (10)
N40.0379 (11)0.0510 (15)0.0264 (11)0.0035 (10)0.0019 (8)0.0024 (9)
N50.0497 (13)0.0308 (12)0.0418 (13)0.0078 (10)0.0101 (10)0.0003 (10)
N60.0462 (14)0.0622 (18)0.0400 (13)0.0127 (12)0.0147 (11)0.0133 (12)
C10.0263 (11)0.0321 (13)0.0191 (10)0.0021 (9)0.0044 (8)0.0014 (9)
C20.0379 (13)0.0335 (15)0.0351 (14)0.0050 (10)0.0100 (10)0.0002 (11)
C30.0335 (13)0.0543 (19)0.0415 (15)0.0063 (12)0.0061 (11)0.0180 (13)
C40.0334 (13)0.074 (2)0.0238 (13)0.0121 (13)0.0019 (10)0.0054 (13)
C50.0398 (14)0.0541 (18)0.0264 (12)0.0147 (12)0.0107 (10)0.0123 (12)
C60.0328 (12)0.0348 (14)0.0300 (12)0.0011 (10)0.0087 (9)0.0034 (10)
C70.0372 (12)0.0295 (13)0.0251 (12)0.0003 (10)0.0079 (9)0.0035 (9)
C80.0321 (12)0.0346 (13)0.0286 (12)0.0021 (10)0.0134 (9)0.0012 (10)
C90.0420 (13)0.0268 (13)0.0321 (12)0.0000 (10)0.0140 (10)0.0003 (10)
C100.0388 (13)0.0374 (15)0.0297 (12)0.0042 (11)0.0122 (10)0.0047 (11)
C110.0360 (12)0.0408 (15)0.0328 (13)0.0059 (11)0.0150 (10)0.0071 (11)
C120.0553 (17)0.0282 (15)0.0506 (17)0.0004 (12)0.0182 (13)0.0064 (12)
Geometric parameters (Å, º) top
S1—C71.760 (2)C2—C31.382 (4)
S1—S22.0427 (10)C2—H20.86 (3)
S2—C81.779 (2)C3—C41.386 (5)
O1—N61.217 (4)C3—H30.94 (4)
O2—N61.219 (3)C4—C51.375 (4)
N1—C71.351 (3)C4—H40.87 (3)
N1—N21.351 (3)C5—C61.391 (3)
N1—C11.441 (3)C5—H50.99 (3)
N2—N31.297 (3)C6—H60.89 (3)
N3—N41.357 (3)C8—C91.389 (3)
N4—C71.318 (3)C9—C101.378 (4)
N5—C121.332 (4)C9—H90.94 (3)
N5—C81.334 (3)C10—C111.375 (4)
N6—C111.467 (3)C10—H100.91 (3)
C1—C21.377 (3)C11—C121.368 (4)
C1—C61.382 (3)C12—H120.88 (4)
C7—S1—S2102.68 (9)C4—C5—C6119.6 (3)
C8—S2—S1105.70 (9)C4—C5—H5118.2 (17)
C7—N1—N2107.75 (18)C6—C5—H5122.2 (18)
C7—N1—C1132.4 (2)C1—C6—C5118.4 (2)
N2—N1—C1119.77 (18)C1—C6—H6121.4 (17)
N3—N2—N1106.6 (2)C5—C6—H6120.1 (17)
N2—N3—N4111.0 (2)N4—C7—N1108.8 (2)
C7—N4—N3105.9 (2)N4—C7—S1125.03 (19)
C12—N5—C8117.2 (2)N1—C7—S1126.05 (18)
O1—N6—O2124.8 (3)N5—C8—C9124.5 (2)
O1—N6—C11117.2 (3)N5—C8—S2109.64 (18)
O2—N6—C11117.9 (3)C9—C8—S2125.8 (2)
C2—C1—C6122.5 (2)C10—C9—C8117.2 (2)
C2—C1—N1119.7 (2)C10—C9—H9119.9 (18)
C6—C1—N1117.6 (2)C8—C9—H9122.9 (18)
C1—C2—C3118.4 (3)C11—C10—C9118.2 (2)
C1—C2—H2123.7 (18)C11—C10—H10121 (2)
C3—C2—H2118.0 (18)C9—C10—H10121 (2)
C2—C3—C4120.1 (3)C12—C11—C10121.0 (2)
C2—C3—H3124 (2)C12—C11—N6119.1 (3)
C4—C3—H3116 (2)C10—C11—N6119.8 (2)
C5—C4—C3121.0 (2)N5—C12—C11121.8 (3)
C5—C4—H4120 (2)N5—C12—H12112 (2)
C3—C4—H4119 (2)C11—C12—H12126 (2)
C7—S1—S2—C876.98 (12)N2—N1—C7—S1176.19 (19)
C7—N1—N2—N30.2 (3)C1—N1—C7—S15.6 (4)
C1—N1—N2—N3178.3 (2)S2—S1—C7—N479.3 (2)
N1—N2—N3—N40.8 (3)S2—S1—C7—N1105.7 (2)
N2—N3—N4—C71.0 (3)C12—N5—C8—C91.1 (4)
C7—N1—C1—C255.4 (4)C12—N5—C8—S2177.8 (2)
N2—N1—C1—C2122.7 (3)S1—S2—C8—N5175.69 (16)
C7—N1—C1—C6127.6 (3)S1—S2—C8—C93.1 (2)
N2—N1—C1—C654.3 (3)N5—C8—C9—C102.2 (4)
C6—C1—C2—C30.1 (4)S2—C8—C9—C10176.44 (18)
N1—C1—C2—C3176.7 (2)C8—C9—C10—C110.8 (4)
C1—C2—C3—C40.1 (4)C9—C10—C11—C121.5 (4)
C2—C3—C4—C50.2 (4)C9—C10—C11—N6176.2 (2)
C3—C4—C5—C60.7 (4)O1—N6—C11—C12167.2 (3)
C2—C1—C6—C50.6 (4)O2—N6—C11—C1212.3 (4)
N1—C1—C6—C5176.3 (2)O1—N6—C11—C1010.5 (4)
C4—C5—C6—C10.9 (4)O2—N6—C11—C10170.0 (2)
N3—N4—C7—N10.9 (3)C8—N5—C12—C111.4 (4)
N3—N4—C7—S1176.67 (19)C10—C11—C12—N52.7 (4)
N2—N1—C7—N40.5 (3)N6—C11—C12—N5174.9 (3)
C1—N1—C7—N4178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N5i0.94 (4)2.61 (4)3.488 (4)156 (3)
C9—H9···S10.95 (3)2.80 (3)3.256 (3)110.5 (19)
C6—H6···Cg1ii0.89 (3)2.84 (3)3.558 (3)139 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC12H8N6O2S2
Mr332.36
Crystal system, space groupMonoclinic, P21/a
Temperature (K)295
a, b, c (Å)7.4161 (2), 21.6740 (6), 9.0312 (3)
β (°) 108.233 (6)
V3)1378.76 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.40
Crystal size (mm)0.22 × 0.20 × 0.15
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.910, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections
9028, 3104, 2656
Rint0.054
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.139, 1.16
No. of reflections3104
No. of parameters231
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.34, 0.26

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
S1—C71.760 (2)S2—C81.779 (2)
S1—S22.0427 (10)N1—C11.441 (3)
C7—S1—S2102.68 (9)N1—C7—S1126.05 (18)
C8—S2—S1105.70 (9)N5—C8—S2109.64 (18)
O1—N6—O2124.8 (3)C9—C8—S2125.8 (2)
N4—C7—S1125.03 (19)
C7—S1—S2—C876.98 (12)S1—S2—C8—N5175.69 (16)
S2—S1—C7—N479.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N5i0.94 (4)2.61 (4)3.488 (4)156 (3)
C9—H9···S10.95 (3)2.80 (3)3.256 (3)110.5 (19)
C6—H6···Cg1ii0.89 (3)2.84 (3)3.558 (3)139 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1/2, y+1/2, z.
 

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