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In the title compound, C10H9N7S2, the dihedral angle between the amino­thia­zole rings is 80.91 (10)°. In the crystal structure, the mol­ecules are linked into chains by N—H...N hydrogen bonds

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045473/hb2543sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045473/hb2543Isup2.hkl
Contains datablock I

CCDC reference: 663815

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.095
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.937 Tmax scaled 0.937 Tmin scaled 0.921
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The molecule of the title compound, (I) (Fig. 1), consists of two aminothiadiazolyl rings and a pyridyl group bridged by a carbon atom with the N donors of the pyridyl and thiadiazolyl groups extending toward the same direction. Dihedral angles between rings (identified by one atom) are S1/S2 = 80.91 (10)°, S1/N1 = 87.08 (9)°, S2/N1 = 73.65 (9)°.

In the crystal, adjacent molecules are linked by N—H···N hydrogen bonds (Table 1) to generate a one-dimensional supramolecular network, as shown in Fig. 2. There are no aromatic π-π stacking interactions involving the thiadiazolyl and pridyl rings.

Experimental top

The title compound, was obtained by the reaction of 2-aminothiadiazole (5.05 g, 0.05 mmol) and 2-pyridylaldehyde (6.5 g, 0.06 mmol) in 100 ml me thanol solution with ten drops of 6 M HCl. The colorless block crystals of (I) were grown via recrystallization in methanol at room temperature.

Refinement top

The H atoms were positionedg geometrically (C—H = 0.93 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier).

Structure description top

The molecule of the title compound, (I) (Fig. 1), consists of two aminothiadiazolyl rings and a pyridyl group bridged by a carbon atom with the N donors of the pyridyl and thiadiazolyl groups extending toward the same direction. Dihedral angles between rings (identified by one atom) are S1/S2 = 80.91 (10)°, S1/N1 = 87.08 (9)°, S2/N1 = 73.65 (9)°.

In the crystal, adjacent molecules are linked by N—H···N hydrogen bonds (Table 1) to generate a one-dimensional supramolecular network, as shown in Fig. 2. There are no aromatic π-π stacking interactions involving the thiadiazolyl and pridyl rings.

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: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 50% probability displacement ellipsoids for the non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the a axis, showing intermolecular N—H···N hydrogen bonds (dashed lines).
(2-Pyridyl)bis(1,3,4-thiadiazol-2-ylamino)methane top
Crystal data top
C10H9N7S2F(000) = 600
Mr = 291.36Dx = 1.500 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 12640 reflections
a = 11.283 (2) Åθ = 3.4–27.5°
b = 8.7613 (18) ŵ = 0.41 mm1
c = 13.151 (3) ÅT = 153 K
β = 97.13 (3)°Block, colourless
V = 1290.0 (5) Å30.20 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker P4
diffractometer
2953 independent reflections
Radiation source: fine-focus sealed tube1908 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1414
Tmin = 0.983, Tmax = 1.000k = 1111
5688 measured reflectionsl = 1717
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) = 0.095H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0492P)2]
where P = (Fo2 + 2Fc2)/3
2953 reflections(Δ/σ)max = 0.001
172 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C10H9N7S2V = 1290.0 (5) Å3
Mr = 291.36Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.283 (2) ŵ = 0.41 mm1
b = 8.7613 (18) ÅT = 153 K
c = 13.151 (3) Å0.20 × 0.18 × 0.16 mm
β = 97.13 (3)°
Data collection top
Bruker P4
diffractometer
2953 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
1908 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 1.000Rint = 0.026
5688 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å3
2953 reflectionsΔρmin = 0.33 e Å3
172 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.39112 (15)0.06831 (18)0.76159 (12)0.0325 (4)
C20.55007 (17)0.0844 (2)0.82008 (16)0.0514 (5)
H20.57930.17140.85520.062*
C30.62985 (18)0.0092 (2)0.77961 (16)0.0526 (5)
H30.71090.01380.78710.063*
C40.58714 (18)0.1363 (2)0.72823 (15)0.0508 (5)
H40.63890.20160.69960.061*
C50.46582 (17)0.1680 (2)0.71879 (13)0.0429 (5)
H50.43530.25490.68430.052*
C60.25742 (15)0.09060 (19)0.75500 (12)0.0345 (4)
H60.21990.01050.75170.041*
C70.17955 (14)0.10493 (19)0.57373 (13)0.0345 (4)
C80.1164 (2)0.0319 (2)0.40249 (15)0.0539 (5)
H80.08640.02180.33370.065*
C90.11296 (16)0.1562 (2)0.86842 (13)0.0381 (4)
C100.0725 (2)0.1710 (3)0.93144 (19)0.0695 (7)
H100.13920.19090.96440.083*
N10.43237 (13)0.05732 (15)0.81182 (12)0.0411 (4)
N20.20837 (14)0.17587 (16)0.66401 (11)0.0410 (4)
H2A0.19780.27280.66820.049*
N30.20509 (14)0.03795 (17)0.55573 (11)0.0433 (4)
N40.16735 (16)0.07900 (18)0.45482 (12)0.0534 (4)
N50.22648 (13)0.16712 (16)0.84586 (11)0.0388 (4)
H5A0.27920.21840.88460.047*
N60.03642 (14)0.05646 (18)0.82607 (13)0.0496 (4)
N70.07234 (16)0.0652 (2)0.86360 (15)0.0657 (5)
S10.10722 (5)0.20038 (6)0.46841 (4)0.04768 (17)
S20.05728 (5)0.27312 (7)0.95736 (4)0.06054 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0361 (10)0.0303 (9)0.0306 (9)0.0021 (7)0.0020 (7)0.0041 (7)
C20.0401 (12)0.0420 (11)0.0689 (14)0.0063 (9)0.0055 (10)0.0012 (10)
C30.0323 (11)0.0615 (14)0.0632 (14)0.0034 (10)0.0028 (10)0.0130 (11)
C40.0488 (13)0.0568 (13)0.0484 (12)0.0155 (10)0.0119 (10)0.0039 (10)
C50.0491 (12)0.0382 (10)0.0414 (11)0.0061 (9)0.0052 (9)0.0050 (8)
C60.0380 (10)0.0303 (9)0.0344 (10)0.0012 (7)0.0018 (7)0.0035 (7)
C70.0313 (10)0.0363 (10)0.0358 (10)0.0020 (7)0.0033 (7)0.0017 (8)
C80.0639 (14)0.0591 (13)0.0366 (11)0.0043 (11)0.0022 (10)0.0014 (10)
C90.0411 (11)0.0380 (10)0.0348 (10)0.0012 (8)0.0026 (8)0.0023 (8)
C100.0451 (14)0.0941 (18)0.0721 (16)0.0046 (12)0.0190 (11)0.0144 (14)
N10.0385 (9)0.0324 (8)0.0506 (9)0.0012 (7)0.0011 (7)0.0057 (7)
N20.0530 (10)0.0298 (8)0.0382 (9)0.0069 (7)0.0023 (7)0.0019 (7)
N30.0527 (10)0.0382 (9)0.0376 (9)0.0060 (7)0.0001 (7)0.0035 (7)
N40.0708 (12)0.0486 (10)0.0386 (10)0.0010 (9)0.0016 (8)0.0094 (8)
N50.0344 (9)0.0441 (9)0.0375 (9)0.0054 (7)0.0024 (7)0.0114 (7)
N60.0388 (9)0.0554 (10)0.0542 (10)0.0067 (8)0.0042 (8)0.0112 (8)
N70.0417 (11)0.0844 (14)0.0713 (13)0.0134 (10)0.0086 (9)0.0122 (11)
S10.0522 (3)0.0472 (3)0.0414 (3)0.0072 (2)0.0028 (2)0.0083 (2)
S20.0534 (4)0.0723 (4)0.0590 (4)0.0035 (3)0.0191 (3)0.0240 (3)
Geometric parameters (Å, º) top
C1—N11.337 (2)C7—N21.344 (2)
C1—C51.382 (2)C7—S11.7330 (18)
C1—C61.513 (2)C8—N41.284 (2)
C2—N11.340 (2)C8—S11.722 (2)
C2—C31.373 (3)C8—H80.9300
C2—H20.9300C9—N61.304 (2)
C3—C41.360 (3)C9—N51.354 (2)
C3—H30.9300C9—S21.7307 (18)
C4—C51.387 (3)C10—N71.287 (3)
C4—H40.9300C10—S21.714 (2)
C5—H50.9300C10—H100.9300
C6—N51.450 (2)N2—H2A0.8600
C6—N21.460 (2)N3—N41.390 (2)
C6—H60.9800N5—H5A0.8600
C7—N31.313 (2)N6—N71.380 (2)
N1—C1—C5121.96 (17)N2—C7—S1121.42 (13)
N1—C1—C6114.72 (14)N4—C8—S1115.44 (15)
C5—C1—C6123.32 (16)N4—C8—H8122.3
N1—C2—C3123.64 (19)S1—C8—H8122.3
N1—C2—H2118.2N6—C9—N5123.27 (16)
C3—C2—H2118.2N6—C9—S2114.12 (14)
C4—C3—C2118.21 (19)N5—C9—S2122.60 (13)
C4—C3—H3120.9N7—C10—S2116.03 (17)
C2—C3—H3120.9N7—C10—H10122.0
C3—C4—C5119.58 (18)S2—C10—H10122.0
C3—C4—H4120.2C1—N1—C2117.80 (16)
C5—C4—H4120.2C7—N2—C6120.86 (14)
C1—C5—C4118.80 (18)C7—N2—H2A119.6
C1—C5—H5120.6C6—N2—H2A119.6
C4—C5—H5120.6C7—N3—N4111.77 (15)
N5—C6—N2109.47 (14)C8—N4—N3112.31 (15)
N5—C6—C1110.65 (14)C9—N5—C6118.61 (14)
N2—C6—C1112.76 (14)C9—N5—H5A120.7
N5—C6—H6107.9C6—N5—H5A120.7
N2—C6—H6107.9C9—N6—N7112.40 (16)
C1—C6—H6107.9C10—N7—N6111.47 (18)
N3—C7—N2124.47 (16)C8—S1—C786.39 (10)
N3—C7—S1114.09 (13)C10—S2—C985.96 (11)
N1—C2—C3—C40.0 (3)S1—C7—N3—N40.01 (19)
C2—C3—C4—C50.4 (3)S1—C8—N4—N30.0 (2)
N1—C1—C5—C40.1 (3)C7—N3—N4—C80.0 (2)
C6—C1—C5—C4179.31 (15)N6—C9—N5—C614.7 (3)
C3—C4—C5—C10.4 (3)S2—C9—N5—C6165.92 (13)
N1—C1—C6—N585.31 (18)N2—C6—N5—C974.84 (19)
C5—C1—C6—N595.21 (18)C1—C6—N5—C9160.28 (14)
N1—C1—C6—N2151.70 (15)N5—C9—N6—N7178.40 (17)
C5—C1—C6—N227.8 (2)S2—C9—N6—N71.1 (2)
C5—C1—N1—C20.2 (3)S2—C10—N7—N60.5 (3)
C6—C1—N1—C2179.69 (15)C9—N6—N7—C100.4 (3)
C3—C2—N1—C10.3 (3)N4—C8—S1—C70.04 (17)
N3—C7—N2—C68.6 (3)N3—C7—S1—C80.03 (15)
S1—C7—N2—C6173.28 (12)N2—C7—S1—C8178.31 (15)
N5—C6—N2—C7151.96 (15)N7—C10—S2—C90.9 (2)
C1—C6—N2—C784.40 (19)N6—C9—S2—C101.09 (16)
N2—C7—N3—N4178.27 (15)N5—C9—S2—C10178.39 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.862.132.866 (2)143
N5—H5A···N3i0.862.272.949 (2)136
Symmetry code: (i) x+1/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC10H9N7S2
Mr291.36
Crystal system, space groupMonoclinic, P21/n
Temperature (K)153
a, b, c (Å)11.283 (2), 8.7613 (18), 13.151 (3)
β (°) 97.13 (3)
V3)1290.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.20 × 0.18 × 0.16
Data collection
DiffractometerBruker P4
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.983, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
5688, 2953, 1908
Rint0.026
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.095, 1.03
No. of reflections2953
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.33

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.862.132.866 (2)143
N5—H5A···N3i0.862.272.949 (2)136
Symmetry code: (i) x+1/2, y+1/2, z+3/2.
 

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