5-({[(E)-Benzyl-idene-amino]-oxy}meth-yl)-1,3,4-thia-diazol-2-amine.

In the mol-ecule of the title compound, C(10)H(10)N(4)OS, the configuration about the C=N double bond is E. The dihedral angle between the thia-diazole and benzene rings is 81.1 (1)°. In the crystal, mol-ecules are linked by N-H⋯N and C-H⋯O hydrogen bonds to form a two-dimensional network parallel with the bc plane.

Related literature

For the biological activity of thia­diazol compounds, see: Cressier et al. (2009 ▶); Ferrari et al. (2011 ▶). For a related structure, see: Boechat et al. (2006 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H10N4OS

M = 234.28

Monoclinic,

a = 14.504 (4) Å

b = 9.272 (3) Å

c = 8.361 (3) Å

β = 106.75 (1)°

V = 1076.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.16 × 0.12 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.956, T max = 0.967

5840 measured reflections

1808 independent reflections

1707 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.09

1808 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.61 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003893/fy2038sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003893/fy2038Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003893/fy2038Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H10N4OS	F(000) = 488
Mr = 234.28	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7867 reflections
a = 14.504 (4) Å	θ = 2.2–31.8°
b = 9.272 (3) Å	µ = 0.28 mm−1
c = 8.361 (3) Å	T = 100 K
β = 106.75 (1)°	Block, colorless
V = 1076.7 (6) Å3	0.16 × 0.12 × 0.12 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1808 independent reflections
Radiation source: fine-focus sealed tube	1707 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→15
Tmin = 0.956, Tmax = 0.967	k = −11→10
5840 measured reflections	l = −9→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0274P)2 + 2.2787P] where P = (Fo2 + 2Fc2)/3
1808 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	−0.01298 (17)	0.3905 (3)	0.3290 (3)	0.0184 (5)
C2	−0.03790 (18)	0.4774 (3)	0.1867 (3)	0.0215 (6)
H2	0.0110	0.5234	0.1502	0.026*
C3	−0.13385 (19)	0.4967 (3)	0.0985 (4)	0.0252 (6)
H3	−0.1507	0.5548	0.0007	0.030*
C4	−0.20545 (19)	0.4310 (3)	0.1531 (4)	0.0264 (6)
H4	−0.2712	0.4441	0.0925	0.032*
C5	−0.18121 (18)	0.3468 (3)	0.2954 (4)	0.0253 (6)
H5	−0.2304	0.3018	0.3320	0.030*
C6	−0.08548 (18)	0.3276 (3)	0.3849 (3)	0.0215 (6)
H6	−0.0692	0.2716	0.4843	0.026*
C7	0.08712 (17)	0.3580 (3)	0.4188 (3)	0.0196 (5)
H7	0.1040	0.3320	0.5335	0.024*
C8	0.30958 (17)	0.3047 (3)	0.3626 (3)	0.0209 (6)
H8A	0.2771	0.2631	0.2517	0.025*
H8B	0.3607	0.2370	0.4222	0.025*
C9	0.35421 (16)	0.4469 (3)	0.3404 (3)	0.0178 (5)
C12	0.42588 (16)	0.6806 (3)	0.3667 (3)	0.0171 (5)
N1	0.15225 (14)	0.3645 (2)	0.3424 (3)	0.0208 (5)
N2	0.39251 (14)	0.4743 (2)	0.2222 (3)	0.0196 (5)
N3	0.43442 (15)	0.6105 (2)	0.2357 (3)	0.0201 (5)
N4	0.45809 (15)	0.8148 (2)	0.4095 (3)	0.0213 (5)
H4A	0.4876	0.8624	0.3475	0.026*
H4B	0.4498	0.8552	0.4995	0.026*
O1	0.24135 (12)	0.3211 (2)	0.4548 (2)	0.0230 (4)
S1	0.36427 (4)	0.58523 (7)	0.48329 (8)	0.0189 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0195 (12)	0.0160 (12)	0.0206 (14)	−0.0003 (9)	0.0072 (10)	−0.0032 (10)
C2	0.0232 (13)	0.0183 (13)	0.0249 (14)	−0.0024 (10)	0.0100 (11)	−0.0010 (10)
C3	0.0291 (14)	0.0167 (13)	0.0267 (15)	0.0039 (10)	0.0029 (11)	0.0012 (11)
C4	0.0184 (12)	0.0258 (14)	0.0328 (16)	0.0029 (10)	0.0040 (11)	−0.0073 (12)
C5	0.0193 (12)	0.0270 (14)	0.0325 (16)	−0.0021 (11)	0.0122 (11)	−0.0026 (12)
C6	0.0224 (12)	0.0194 (13)	0.0243 (14)	0.0006 (10)	0.0095 (11)	0.0000 (10)
C7	0.0206 (12)	0.0162 (12)	0.0222 (14)	−0.0008 (10)	0.0064 (10)	0.0007 (10)
C8	0.0168 (11)	0.0216 (13)	0.0260 (15)	0.0008 (10)	0.0090 (10)	−0.0007 (10)
C9	0.0144 (11)	0.0186 (12)	0.0202 (13)	0.0033 (9)	0.0049 (10)	0.0010 (10)
C12	0.0119 (10)	0.0237 (13)	0.0163 (13)	0.0037 (9)	0.0051 (9)	0.0027 (10)
N1	0.0165 (10)	0.0211 (11)	0.0218 (12)	−0.0007 (8)	0.0007 (9)	0.0007 (9)
N2	0.0180 (10)	0.0227 (11)	0.0190 (11)	0.0005 (8)	0.0067 (8)	−0.0010 (9)
N3	0.0200 (10)	0.0203 (11)	0.0212 (12)	0.0026 (8)	0.0079 (9)	0.0001 (9)
N4	0.0257 (11)	0.0207 (11)	0.0210 (12)	−0.0044 (9)	0.0122 (9)	−0.0029 (9)
O1	0.0157 (8)	0.0283 (10)	0.0239 (10)	0.0009 (7)	0.0038 (7)	0.0023 (8)
S1	0.0204 (3)	0.0219 (3)	0.0177 (4)	−0.0020 (2)	0.0106 (2)	−0.0010 (2)

C1—C2	1.396 (4)	C8—O1	1.426 (3)
C1—C6	1.396 (4)	C8—C9	1.503 (3)
C1—C7	1.461 (3)	C8—H8A	0.9900
C2—C3	1.386 (4)	C8—H8B	0.9900
C2—H2	0.9500	C9—N2	1.291 (3)
C3—C4	1.390 (4)	C9—S1	1.730 (3)
C3—H3	0.9500	C12—N3	1.309 (3)
C4—C5	1.381 (4)	C12—N4	1.341 (3)
C4—H4	0.9500	C12—S1	1.742 (2)
C5—C6	1.386 (4)	N1—O1	1.419 (3)
C5—H5	0.9500	N2—N3	1.392 (3)
C6—H6	0.9500	N4—H4A	0.8800
C7—N1	1.285 (3)	N4—H4B	0.8800
C7—H7	0.9500
C2—C1—C6	119.5 (2)	O1—C8—C9	111.4 (2)
C2—C1—C7	122.2 (2)	O1—C8—H8A	109.4
C6—C1—C7	118.3 (2)	C9—C8—H8A	109.4
C3—C2—C1	120.1 (2)	O1—C8—H8B	109.4
C3—C2—H2	119.9	C9—C8—H8B	109.4
C1—C2—H2	119.9	H8A—C8—H8B	108.0
C2—C3—C4	120.0 (3)	N2—C9—C8	124.3 (2)
C2—C3—H3	120.0	N2—C9—S1	114.39 (19)
C4—C3—H3	120.0	C8—C9—S1	121.23 (19)
C5—C4—C3	120.1 (2)	N3—C12—N4	125.0 (2)
C5—C4—H4	119.9	N3—C12—S1	113.79 (19)
C3—C4—H4	119.9	N4—C12—S1	121.15 (19)
C4—C5—C6	120.3 (2)	C7—N1—O1	108.5 (2)
C4—C5—H5	119.9	C9—N2—N3	113.0 (2)
C6—C5—H5	119.9	C12—N3—N2	112.0 (2)
C5—C6—C1	120.0 (3)	C12—N4—H4A	120.0
C5—C6—H6	120.0	C12—N4—H4B	120.0
C1—C6—H6	120.0	H4A—N4—H4B	120.0
N1—C7—C1	119.9 (2)	N1—O1—C8	108.28 (19)
N1—C7—H7	120.0	C9—S1—C12	86.84 (12)
C1—C7—H7	120.0
C6—C1—C2—C3	−2.3 (4)	C1—C7—N1—O1	−177.0 (2)
C7—C1—C2—C3	175.2 (2)	C8—C9—N2—N3	−176.0 (2)
C1—C2—C3—C4	0.9 (4)	S1—C9—N2—N3	0.3 (3)
C2—C3—C4—C5	0.1 (4)	N4—C12—N3—N2	−178.9 (2)
C3—C4—C5—C6	0.2 (4)	S1—C12—N3—N2	−0.6 (3)
C4—C5—C6—C1	−1.6 (4)	C9—N2—N3—C12	0.2 (3)
C2—C1—C6—C5	2.6 (4)	C7—N1—O1—C8	170.3 (2)
C7—C1—C6—C5	−175.0 (2)	C9—C8—O1—N1	83.4 (2)
C2—C1—C7—N1	−24.1 (4)	N2—C9—S1—C12	−0.50 (19)
C6—C1—C7—N1	153.4 (2)	C8—C9—S1—C12	175.9 (2)
O1—C8—C9—N2	−156.5 (2)	N3—C12—S1—C9	0.63 (19)
O1—C8—C9—S1	27.5 (3)	N4—C12—S1—C9	179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N2i	0.88	2.24	3.077 (3)	159
N4—H4B···N3ii	0.88	2.07	2.929 (3)	164
C8—H8A···O1iii	0.99	2.51	3.468 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N2i	0.88	2.24	3.077 (3)	159
N4—H4B⋯N3ii	0.88	2.07	2.929 (3)	164
C8—H8A⋯O1iii	0.99	2.51	3.468 (3)	163

Symmetry codes: (i) ; (ii) ; (iii) .