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The title compound, C8H6N4S, was obtained via the reaction of 2-amino­thia­diazole with pyridine-2-carbaldehyde in methanol solution in a 1:1 stoichiometry. The mol­ecule consists of two amino­thia­zolyl and two pyridyl groups linked by a C=C double bond which lies on a crystallographic centre of symmetry. Adjacent mol­ecules are linked by N—H...S hydrogen bonds to generate a one-dimensional supra­molecular chain structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046673/dn2232sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046673/dn2232Isup2.hkl
Contains datablock I

CCDC reference: 663848

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.101
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The molecule of the title compound consists of two aminothiazolyl and two pyridyl groups linked by a CC double bond which lies on a crystallographic centre of symmetry (Fig. 1).

The adjacent molecules are linked by N3—H3A···S1i (Table 1) hydrogen bonds to generate a one dimensional supramolecular network strcucture (Fig. 2). There are no aromatic ππ stacking interactions.

Related literature top

[Please provide at least one reference to related literature]

Experimental top

The title compound, C10H9N7S2, was synthesized via the reflux reaction of 2-aminothiazole (10.711 g, 0.1 mol) and 2-pyridylaldehyde (10.113 g, 0.1 mol) in 1:1 stoichiometry in 200 ml me thanol solution with 1 ml HCl (6 M) for 24 h. The block crystals suitable for single-crystal X-ray diffraction were obtained via recrystallization of the powder in methanol at room temperature.

Refinement top

All H atoms attached to C and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(C or N).

Structure description top

The molecule of the title compound consists of two aminothiazolyl and two pyridyl groups linked by a CC double bond which lies on a crystallographic centre of symmetry (Fig. 1).

The adjacent molecules are linked by N3—H3A···S1i (Table 1) hydrogen bonds to generate a one dimensional supramolecular network strcucture (Fig. 2). There are no aromatic ππ stacking interactions.

[Please provide at least one reference to related literature]

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the vatom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. [Symmetry code: (i) -x + 1, -y + 1, -z + 1]
[Figure 2] Fig. 2. Partial packing view of (I) showing intermolecular N—H···S hydrogen bonds (dashed lines). H atoms not involved in hydrogen bondings have been omitted for carity. [Symmetry code: (i) -x + 1, -y + 1, -z + 1; (ii) x - 1, y, z]
1,2-Di-2-pyridyl-1,2-bis(1,3,4-thiadiazol-2-ylamino)ethane top
Crystal data top
C16H12N8S2Z = 1
Mr = 380.46F(000) = 196
Triclinic, P1Dx = 1.551 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4720 (11) ÅCell parameters from 4677 reflections
b = 7.9623 (16) Åθ = 3.4–27.5°
c = 9.7363 (19) ŵ = 0.35 mm1
α = 91.01 (3)°T = 153 K
β = 93.96 (3)°Block, colourless
γ = 105.57 (3)°0.20 × 0.18 × 0.14 mm
V = 407.38 (15) Å3
Data collection top
Bruker P4
diffractometer
1447 independent reflections
Radiation source: fine-focus sealed tube1032 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 25.2°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.926, Tmax = 0.943k = 99
2787 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0547P)2 + 0.0338P]
where P = (Fo2 + 2Fc2)/3
1447 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
C16H12N8S2γ = 105.57 (3)°
Mr = 380.46V = 407.38 (15) Å3
Triclinic, P1Z = 1
a = 5.4720 (11) ÅMo Kα radiation
b = 7.9623 (16) ŵ = 0.35 mm1
c = 9.7363 (19) ÅT = 153 K
α = 91.01 (3)°0.20 × 0.18 × 0.14 mm
β = 93.96 (3)°
Data collection top
Bruker P4
diffractometer
1447 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1032 reflections with I > 2σ(I)
Tmin = 0.926, Tmax = 0.943Rint = 0.024
2787 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.02Δρmax = 0.34 e Å3
1447 reflectionsΔρmin = 0.42 e Å3
118 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7059 (5)0.2732 (3)0.9578 (3)0.0497 (7)
H10.81870.23331.01590.060*
C20.4851 (4)0.3957 (3)0.7878 (2)0.0314 (5)
C30.5411 (4)0.5333 (3)0.5653 (2)0.0312 (5)
C40.7705 (4)0.6802 (3)0.6017 (2)0.0317 (5)
N40.9649 (3)0.7030 (3)0.5189 (2)0.0363 (5)
C51.1725 (4)0.8343 (3)0.5528 (3)0.0423 (6)
H51.30710.85110.49660.051*
C61.1987 (5)0.9445 (3)0.6642 (3)0.0463 (7)
H61.34811.03270.68420.056*
C70.9988 (5)0.9226 (3)0.7473 (3)0.0452 (7)
H71.00980.99730.82330.054*
N10.4702 (4)0.2465 (3)0.9794 (2)0.0489 (6)
N20.3381 (4)0.3183 (3)0.8806 (2)0.0405 (5)
N30.3944 (3)0.4696 (3)0.67620 (18)0.0348 (5)
H30.24040.47750.67370.042*
C80.7827 (4)0.7882 (3)0.7156 (2)0.0386 (6)
H80.64620.77050.77050.046*
S10.79840 (11)0.38809 (9)0.81359 (7)0.0459 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0555 (17)0.0585 (18)0.0389 (15)0.0214 (14)0.0033 (13)0.0134 (13)
C20.0307 (12)0.0341 (13)0.0278 (12)0.0059 (10)0.0037 (10)0.0023 (10)
C30.0262 (11)0.0370 (14)0.0317 (11)0.0102 (10)0.0042 (9)0.0053 (10)
C40.0284 (12)0.0354 (14)0.0313 (13)0.0087 (10)0.0006 (10)0.0078 (10)
N40.0277 (10)0.0418 (12)0.0378 (11)0.0064 (9)0.0041 (9)0.0044 (9)
C50.0292 (12)0.0432 (15)0.0507 (16)0.0024 (11)0.0057 (11)0.0040 (13)
C60.0378 (14)0.0378 (15)0.0573 (18)0.0015 (11)0.0024 (13)0.0002 (14)
C70.0497 (15)0.0376 (15)0.0447 (15)0.0070 (12)0.0012 (13)0.0038 (12)
N10.0583 (15)0.0548 (14)0.0349 (12)0.0153 (11)0.0095 (10)0.0140 (10)
N20.0397 (11)0.0457 (13)0.0354 (11)0.0076 (9)0.0112 (9)0.0076 (10)
N30.0263 (10)0.0490 (13)0.0300 (10)0.0102 (9)0.0060 (8)0.0077 (9)
C80.0385 (14)0.0432 (15)0.0341 (14)0.0103 (11)0.0053 (11)0.0019 (12)
S10.0346 (4)0.0632 (5)0.0426 (4)0.0163 (3)0.0060 (3)0.0156 (3)
Geometric parameters (Å, º) top
C1—N11.283 (3)N4—C51.338 (3)
C1—S11.720 (3)C5—C61.358 (4)
C1—H10.9300C5—H50.9300
C2—N21.303 (3)C6—C71.380 (4)
C2—N31.370 (3)C6—H60.9300
C2—S11.733 (2)C7—C81.378 (3)
C3—C3i1.367 (4)C7—H70.9300
C3—N31.410 (3)N1—N21.386 (3)
C3—C41.485 (3)N3—H30.8600
C4—N41.354 (3)C8—H80.9300
C4—C81.378 (3)
N1—C1—S1115.2 (2)C5—C6—C7118.6 (2)
N1—C1—H1122.4C5—C6—H6120.7
S1—C1—H1122.4C7—C6—H6120.7
N2—C2—N3122.2 (2)C8—C7—C6118.8 (2)
N2—C2—S1114.43 (18)C8—C7—H7120.6
N3—C2—S1123.33 (16)C6—C7—H7120.6
C3i—C3—N3119.7 (2)C1—N1—N2112.67 (19)
C3i—C3—C4125.0 (2)C2—N2—N1111.6 (2)
N3—C3—C4115.10 (19)C2—N3—C3123.21 (19)
N4—C4—C8121.9 (2)C2—N3—H3118.4
N4—C4—C3117.4 (2)C3—N3—H3118.4
C8—C4—C3120.74 (19)C4—C8—C7119.4 (2)
C5—N4—C4117.3 (2)C4—C8—H8120.3
N4—C5—C6124.0 (2)C7—C8—H8120.3
N4—C5—H5118.0C1—S1—C286.18 (12)
C6—C5—H5118.0
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···S1ii0.862.793.513 (2)143
Symmetry code: (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC16H12N8S2
Mr380.46
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)5.4720 (11), 7.9623 (16), 9.7363 (19)
α, β, γ (°)91.01 (3), 93.96 (3), 105.57 (3)
V3)407.38 (15)
Z1
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.20 × 0.18 × 0.14
Data collection
DiffractometerBruker P4
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.926, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections
2787, 1447, 1032
Rint0.024
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.101, 1.02
No. of reflections1447
No. of parameters118
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.42

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···S1i0.862.793.513 (2)142.9
Symmetry code: (i) x1, y, z.
 

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