2-Amino-5-(salicylideneamino)-1,3,4-thia­diazole

Guo, Z.; Yang, M.; Zhang, R.; Sun, Y.

doi:10.1107/S1600536807059715

2-Amino-5-(salicylideneamino)-1,3,4-thiadiazole

In the title compound, C₉H₈N₄OS, there are two independent molecules in the asymmetric unit. The C—N—C—S torsion angles in the two molecules are 13.9 (4) and 14.3 (5)°. In the crystal structure, intermolecular N—H

N and O—H

S hydrogen bonds result in the formation of one-dimensional chains of rings propagating along [100].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059715/lh2565sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059715/lh2565Isup2.hkl Contains datablock I

CCDC reference: 646689

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.048
wR factor = 0.123
Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  S1      ..       2.98 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 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

Schiff bases have been intensively investigated recently owing to their diverse biological activities, such as antibacterial, antitumor activities etc. (Yang et al., 2000; Mondal et al., 2001; Tarafder et al., 2002). On the other hand, heterocycles in organic synthesis is a current research (Meyers, 1974) and lots of organic heterocyclic compounds have been synthesized (Raper, 1985; Streubel, 2002; Baker & Jones, 2005) to study their various characteristics.

We are interested in 2,5-dithiobiurea and salicylaldehyde and report here the structure of the title compound. The asymmetric unit of the title compound contains two crystallographically independent molecules, with almost identical bond lengths and angles. The asymmetric unit and atom numbering scheme are shown in (Fig. 1).

The title compound comprises a 2-amino-1,3,4- thiadiazole moiety and 2-hydroxyphenyl group linked by a C=N bond which has a Z geometry. In this Z isomer, the C3—C4 bond is trans with respect to the N3—C1 bond. The geometries of the two molecules in the asymmetric unit are essentially the same, so only one independent molecule is discussed in detail here.

The bond angles around atoms N3 and C3 deviate from 120 ° and this is in general agreement with observation for a similar type of compound (Cheng et al., 2006). The angles C3=N3—C1, C4—C3=N3 and H3—C3—C4 [118.33, 123.71 and 118.18 °, respectively] are distorted as a consequence of the strain induced by the double-bond linkage at C3=N3.

For the five-membered 1,3,4-thiadiazole ring, the N1—N2 bond length (1.384 (4) Å) and the C=N bond lengths (C1=N1 1.303 (4) Å and C2=N2 1.310 (4) Å, respectively) are consistent with those reported in the literature (Ma, Zhang et al., 2004); the C—S bond lengths (C1—S1 1.745 (4) Å and C2—S1 1.733 (4) Å, respectively) are consistent with literature reported (Ma, Li et al., 2004).

The molecular structure and crystal packing of are stabilized by intermolecular N—H···N and O—H···S hydrogen bonds. N—H···N hydrogen bonds generate centrosymmetric R₂²8 (Etter, 1990) rings (Fig.2), forming dimers which are linked through the N—H···N hydrogen bonds to form a second type of ring motif, of R₄⁴10 type. The combination of these rings produces a linear chains, which run along [100] and are stabilized by weak intermolecular O—H···S hydrogen bonds.

Related literature top

For related literature, see: Baker & Jones (2005); Ma, Li et al. (2004); Ma, Zhang et al. (2004); Meyers (1974); Mondal et al. (2001); Raper (1985); Streubel (2002); Tarafder et al. (2002); Yang et al. (2000).

For related literature, see: Cheng et al. (2006); Etter (1990).

Experimental top

The reaction was carried out under nitrogen atmosphere with use of standard Schlenk technique. The 2,5-dithiobiurea (0.150 g, 1 mmol) was added to the solution of ethanol (20 ml) with sodium ethoxide (0.136 g, 2 mmol) and stirred for 10 min, and then added salicyladehyde (0.112 g,1 mmol) to the mixture, the mixture was stirred at 353 K and then filtered. an pale yellow solution was obtained, which was filtered. The filtrate was left undisturbed at room temperature for one week. Crystals of the title compound suitable for X-ray analysis were grown from an ethanol solution. yield 65%. NMR(CHCl₃):(H) 11.23 (H1, s), 7.02 (H8, s), 7.09 (H6, s), 7.26 (H2, s), 7.56 (H1, s), 7.69 (H1, s), 8.38 (H1, s); (C) 118.1 (C6), 120.8 (C4), 121.8 (C8), 132.6 (C9), 132.9 (C7), 160.5 (C3), 161.4 (C5), 162.0 (C2), 164.2 (C1).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure of the title compound. Hydrogen atoms not involved in hydrogen bonds (dashed lines)have been removed for clarity.

2-Amino-5-(salicylideneamino)-1,3,4-thiadiazole top

Crystal data top

C₉H₈N₄OS	F(000) = 912
M_r = 220.25	D_x = 1.521 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1496 reflections
a = 5.841 (2) Å	θ = 2.3–21.6°
b = 30.421 (10) Å	µ = 0.31 mm⁻¹
c = 10.915 (4) Å	T = 298 K
β = 97.282 (4)°	Block, orange
V = 1923.7 (11) Å³	0.22 × 0.15 × 0.11 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	3314 independent reflections
Radiation source: fine-focus sealed tube	1830 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→4
T_min = 0.932, T_max = 0.958	k = −36→33
9736 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.050P)²] where P = (F_o² + 2F_c²)/3
3314 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₉H₈N₄OS	V = 1923.7 (11) Å³
M_r = 220.25	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.841 (2) Å	µ = 0.31 mm⁻¹
b = 30.421 (10) Å	T = 298 K
c = 10.915 (4) Å	0.22 × 0.15 × 0.11 mm
β = 97.282 (4)°

Data collection top

Bruker SMART CCD diffractometer	3314 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1830 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.958	R_int = 0.061
9736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
3314 reflections	Δρ_min = −0.27 e Å⁻³
271 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.0020 (5)	0.02475 (9)	1.1793 (3)	0.0413 (8)
N2	0.1711 (5)	0.00077 (9)	1.2504 (3)	0.0411 (8)
N3	−0.0552 (5)	0.07223 (9)	1.0065 (3)	0.0389 (7)
N4	0.5670 (5)	−0.01561 (10)	1.2623 (3)	0.0485 (9)
H4A	0.5632	−0.0329	1.3243	0.058*
H4B	0.6945	−0.0114	1.2324	0.058*
N5	0.2979 (5)	0.09155 (10)	0.4459 (3)	0.0503 (9)
N6	0.4661 (5)	0.06510 (10)	0.5069 (3)	0.0452 (8)
N7	0.2222 (5)	0.14339 (9)	0.2877 (3)	0.0413 (8)
N8	0.8524 (5)	0.04549 (10)	0.5046 (3)	0.0503 (9)
H8A	0.8483	0.0271	0.5642	0.060*
H8B	0.9777	0.0490	0.4720	0.060*
O1	−0.4115 (5)	0.12430 (9)	0.9319 (3)	0.0615 (8)
H1	−0.3375	0.1058	0.9750	0.092*
O2	−0.1463 (5)	0.19460 (9)	0.2563 (3)	0.0648 (8)
H2	−0.0528	0.1776	0.2931	0.097*
S1	0.37598 (16)	0.03882 (3)	1.08484 (9)	0.0434 (3)
S2	0.66006 (17)	0.10490 (3)	0.34039 (9)	0.0464 (3)
C1	0.0808 (6)	0.04590 (11)	1.0896 (3)	0.0349 (9)
C2	0.3737 (6)	0.00484 (11)	1.2122 (3)	0.0367 (9)
C3	0.0284 (6)	0.08513 (11)	0.9074 (3)	0.0392 (9)
H3	0.1723	0.0745	0.8936	0.047*
C4	−0.0879 (7)	0.11451 (11)	0.8191 (3)	0.0398 (9)
C5	−0.3019 (7)	0.13374 (12)	0.8338 (4)	0.0451 (10)
C6	−0.3961 (7)	0.16421 (13)	0.7469 (4)	0.0569 (11)
H6	−0.5356	0.1777	0.7564	0.068*
C7	−0.2859 (8)	0.17457 (13)	0.6474 (4)	0.0596 (12)
H7	−0.3534	0.1947	0.5898	0.072*
C8	−0.0757 (8)	0.15570 (14)	0.6304 (4)	0.0610 (12)
H8	−0.0019	0.1631	0.5626	0.073*
C9	0.0205 (7)	0.12576 (12)	0.7163 (3)	0.0499 (10)
H9	0.1606	0.1127	0.7058	0.060*
C10	0.3698 (6)	0.11467 (11)	0.3573 (3)	0.0401 (9)
C11	0.6628 (6)	0.06866 (11)	0.4623 (3)	0.0390 (9)
C12	0.2767 (7)	0.15904 (11)	0.1865 (3)	0.0421 (9)
H12	0.4159	0.1506	0.1607	0.051*
C13	0.1291 (7)	0.18946 (11)	0.1108 (3)	0.0412 (9)
C14	−0.0756 (7)	0.20601 (11)	0.1478 (4)	0.0433 (10)
C15	−0.2124 (7)	0.23435 (12)	0.0721 (4)	0.0577 (12)
H15	−0.3474	0.2454	0.0972	0.069*
C16	−0.1507 (9)	0.24629 (13)	−0.0395 (4)	0.0629 (13)
H16	−0.2458	0.2650	−0.0907	0.075*
C17	0.0516 (9)	0.23096 (14)	−0.0776 (4)	0.0648 (13)
H17	0.0936	0.2396	−0.1534	0.078*
C18	0.1897 (8)	0.20292 (13)	−0.0031 (3)	0.0530 (11)
H18	0.3260	0.1927	−0.0288	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0324 (18)	0.0468 (18)	0.0457 (19)	0.0019 (16)	0.0083 (16)	0.0064 (15)
N2	0.0336 (19)	0.0492 (19)	0.0400 (18)	0.0019 (16)	0.0033 (15)	0.0111 (15)
N3	0.0323 (17)	0.0412 (18)	0.0431 (19)	0.0031 (15)	0.0049 (15)	0.0009 (15)
N4	0.0322 (18)	0.062 (2)	0.054 (2)	0.0110 (17)	0.0119 (16)	0.0189 (16)
N5	0.038 (2)	0.060 (2)	0.054 (2)	0.0055 (18)	0.0101 (17)	0.0130 (18)
N6	0.0361 (19)	0.051 (2)	0.049 (2)	0.0029 (17)	0.0071 (16)	0.0164 (16)
N7	0.0401 (19)	0.0381 (18)	0.0455 (19)	0.0030 (16)	0.0041 (16)	0.0062 (15)
N8	0.0321 (18)	0.063 (2)	0.057 (2)	0.0056 (17)	0.0094 (16)	0.0253 (17)
O1	0.0464 (18)	0.0703 (19)	0.071 (2)	0.0158 (15)	0.0218 (16)	0.0209 (16)
O2	0.057 (2)	0.0624 (18)	0.080 (2)	0.0175 (15)	0.0267 (17)	0.0217 (16)
S1	0.0338 (6)	0.0514 (6)	0.0460 (6)	0.0026 (5)	0.0087 (5)	0.0126 (5)
S2	0.0355 (6)	0.0537 (6)	0.0505 (6)	0.0024 (5)	0.0084 (5)	0.0150 (5)
C1	0.029 (2)	0.034 (2)	0.041 (2)	0.0009 (17)	0.0047 (17)	−0.0043 (17)
C2	0.029 (2)	0.041 (2)	0.040 (2)	0.0006 (18)	0.0028 (18)	0.0004 (17)
C3	0.037 (2)	0.038 (2)	0.044 (2)	−0.0020 (18)	0.0071 (19)	−0.0019 (18)
C4	0.037 (2)	0.040 (2)	0.041 (2)	−0.0031 (19)	0.0001 (18)	0.0064 (18)
C5	0.039 (2)	0.045 (2)	0.050 (3)	−0.001 (2)	−0.002 (2)	0.005 (2)
C6	0.047 (3)	0.051 (3)	0.068 (3)	0.009 (2)	−0.007 (2)	0.010 (2)
C7	0.071 (3)	0.052 (3)	0.052 (3)	0.006 (2)	−0.007 (2)	0.012 (2)
C8	0.069 (3)	0.066 (3)	0.048 (3)	−0.006 (3)	0.006 (2)	0.006 (2)
C9	0.051 (3)	0.051 (2)	0.047 (2)	0.001 (2)	0.005 (2)	0.006 (2)
C10	0.039 (2)	0.038 (2)	0.043 (2)	−0.0005 (19)	0.0028 (19)	0.0018 (18)
C11	0.035 (2)	0.041 (2)	0.040 (2)	−0.0040 (19)	0.0025 (18)	0.0059 (17)
C12	0.034 (2)	0.041 (2)	0.051 (3)	0.0052 (19)	0.0030 (19)	−0.0048 (19)
C13	0.042 (2)	0.034 (2)	0.046 (2)	−0.0014 (19)	0.0005 (19)	−0.0001 (18)
C14	0.040 (2)	0.030 (2)	0.060 (3)	−0.0021 (19)	0.004 (2)	0.0052 (19)
C15	0.046 (3)	0.044 (2)	0.080 (3)	0.006 (2)	−0.005 (2)	0.006 (2)
C16	0.070 (3)	0.041 (3)	0.069 (3)	0.000 (2)	−0.023 (3)	0.005 (2)
C17	0.091 (4)	0.054 (3)	0.047 (3)	−0.010 (3)	−0.005 (3)	0.005 (2)
C18	0.058 (3)	0.057 (3)	0.044 (3)	−0.002 (2)	0.005 (2)	0.002 (2)

Geometric parameters (Å, º) top

N1—C1	1.303 (4)	C3—C4	1.423 (5)
N1—N2	1.384 (4)	C3—H3	0.9300
N2—C2	1.310 (4)	C4—C9	1.399 (5)
N3—C3	1.302 (4)	C4—C5	1.407 (5)
N3—C1	1.383 (4)	C5—C6	1.389 (5)
N4—C2	1.343 (4)	C6—C7	1.367 (5)
N4—H4A	0.8600	C6—H6	0.9300
N4—H4B	0.8600	C7—C8	1.389 (6)
N5—C10	1.307 (4)	C7—H7	0.9300
N5—N6	1.375 (4)	C8—C9	1.375 (5)
N6—C11	1.308 (4)	C8—H8	0.9300
N7—C12	1.279 (4)	C9—H9	0.9300
N7—C10	1.385 (4)	C12—C13	1.450 (5)
N8—C11	1.344 (4)	C12—H12	0.9300
N8—H8A	0.8600	C13—C18	1.397 (5)
N8—H8B	0.8600	C13—C14	1.403 (5)
O1—C5	1.346 (4)	C14—C15	1.377 (5)
O1—H1	0.8200	C15—C16	1.363 (5)
O2—C14	1.349 (4)	C15—H15	0.9300
O2—H2	0.8200	C16—C17	1.382 (6)
S1—C2	1.733 (4)	C16—H16	0.9300
S1—C1	1.745 (4)	C17—C18	1.368 (6)
S2—C11	1.726 (4)	C17—H17	0.9300
S2—C10	1.754 (4)	C18—H18	0.9300

C1—N1—N2	112.8 (3)	C6—C7—H7	119.2
C2—N2—N1	112.3 (3)	C8—C7—H7	119.2
C3—N3—C1	118.3 (3)	C9—C8—C7	118.3 (4)
C2—N4—H4A	120.0	C9—C8—H8	120.9
C2—N4—H4B	120.0	C7—C8—H8	120.9
H4A—N4—H4B	120.0	C8—C9—C4	121.4 (4)
C10—N5—N6	113.4 (3)	C8—C9—H9	119.3
C11—N6—N5	112.2 (3)	C4—C9—H9	119.3
C12—N7—C10	120.2 (3)	N5—C10—N7	120.6 (3)
C11—N8—H8A	120.0	N5—C10—S2	113.1 (3)
C11—N8—H8B	120.0	N7—C10—S2	126.3 (3)
H8A—N8—H8B	120.0	N6—C11—N8	123.6 (3)
C5—O1—H1	109.5	N6—C11—S2	114.7 (3)
C14—O2—H2	109.5	N8—C11—S2	121.8 (3)
C2—S1—C1	86.66 (17)	N7—C12—C13	122.3 (3)
C11—S2—C10	86.66 (18)	N7—C12—H12	118.8
N1—C1—N3	123.4 (3)	C13—C12—H12	118.8
N1—C1—S1	113.9 (3)	C18—C13—C14	118.2 (4)
N3—C1—S1	122.7 (3)	C18—C13—C12	119.7 (4)
N2—C2—N4	125.0 (3)	C14—C13—C12	122.1 (3)
N2—C2—S1	114.3 (3)	O2—C14—C15	118.0 (4)
N4—C2—S1	120.7 (3)	O2—C14—C13	121.8 (3)
N3—C3—C4	123.7 (3)	C15—C14—C13	120.2 (4)
N3—C3—H3	118.1	C16—C15—C14	120.3 (4)
C4—C3—H3	118.1	C16—C15—H15	119.9
C9—C4—C5	119.3 (3)	C14—C15—H15	119.9
C9—C4—C3	118.1 (4)	C15—C16—C17	120.8 (4)
C5—C4—C3	122.6 (3)	C15—C16—H16	119.6
O1—C5—C6	119.9 (4)	C17—C16—H16	119.6
O1—C5—C4	121.4 (3)	C18—C17—C16	119.6 (4)
C6—C5—C4	118.7 (4)	C18—C17—H17	120.2
C7—C6—C5	120.7 (4)	C16—C17—H17	120.2
C7—C6—H6	119.6	C17—C18—C13	121.0 (4)
C5—C6—H6	119.6	C17—C18—H18	119.5
C6—C7—C8	121.6 (4)	C13—C18—H18	119.5

C1—N1—N2—C2	0.3 (4)	C3—C4—C9—C8	−176.6 (3)
C10—N5—N6—C11	−0.4 (5)	N6—N5—C10—N7	−179.3 (3)
N2—N1—C1—N3	−179.7 (3)	N6—N5—C10—S2	0.7 (4)
N2—N1—C1—S1	−0.7 (4)	C12—N7—C10—N5	−165.7 (3)
C3—N3—C1—N1	−167.2 (3)	C12—N7—C10—S2	14.3 (5)
C3—N3—C1—S1	13.9 (4)	C11—S2—C10—N5	−0.6 (3)
C2—S1—C1—N1	0.7 (3)	C11—S2—C10—N7	179.3 (3)
C2—S1—C1—N3	179.7 (3)	N5—N6—C11—N8	−178.6 (3)
N1—N2—C2—N4	−178.4 (3)	N5—N6—C11—S2	−0.1 (4)
N1—N2—C2—S1	0.2 (4)	C10—S2—C11—N6	0.4 (3)
C1—S1—C2—N2	−0.5 (3)	C10—S2—C11—N8	178.9 (3)
C1—S1—C2—N4	178.1 (3)	C10—N7—C12—C13	−179.5 (3)
C1—N3—C3—C4	−175.8 (3)	N7—C12—C13—C18	−175.3 (3)
N3—C3—C4—C9	−179.9 (3)	N7—C12—C13—C14	4.4 (5)
N3—C3—C4—C5	2.6 (5)	C18—C13—C14—O2	179.9 (3)
C9—C4—C5—O1	−179.2 (3)	C12—C13—C14—O2	0.2 (5)
C3—C4—C5—O1	−1.7 (6)	C18—C13—C14—C15	0.7 (5)
C9—C4—C5—C6	−1.6 (5)	C12—C13—C14—C15	−179.0 (3)
C3—C4—C5—C6	176.0 (3)	O2—C14—C15—C16	−178.8 (3)
O1—C5—C6—C7	179.3 (4)	C13—C14—C15—C16	0.4 (6)
C4—C5—C6—C7	1.5 (6)	C14—C15—C16—C17	−1.3 (6)
C5—C6—C7—C8	−1.0 (7)	C15—C16—C17—C18	1.0 (6)
C6—C7—C8—C9	0.4 (6)	C16—C17—C18—C13	0.1 (6)
C7—C8—C9—C4	−0.4 (6)	C14—C13—C18—C17	−1.0 (6)
C5—C4—C9—C8	1.0 (6)	C12—C13—C18—C17	178.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ⁱ	0.82	2.98	3.408 (3)	115
O2—H2···N7	0.82	1.92	2.644 (4)	147
O1—H1···N3	0.82	1.93	2.660 (4)	147
N8—H8B···N5ⁱⁱ	0.86	2.32	3.093 (4)	150
N8—H8A···N2ⁱⁱⁱ	0.86	2.21	3.041 (4)	162
N4—H4B···N1ⁱⁱ	0.86	2.24	3.061 (4)	159
N4—H4A···N6ⁱⁱⁱ	0.86	2.11	2.962 (4)	170

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₉H₈N₄OS
M_r	220.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	5.841 (2), 30.421 (10), 10.915 (4)
β (°)	97.282 (4)
V (Å³)	1923.7 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.22 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	9736, 3314, 1830
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.123, 1.00
No. of reflections	3314
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.27

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).