(E)-2-[(E)-3-(Hy-droxy-imino)-butan-2-yl-idene]-N-methyl-hydrazinecarbothio-amide.

In the title compound, C(6)H(12)N(4)OS, an intra-molecular N-H⋯N hydrogen-bond is present giving rise to an S(5) ring motif. In the crystal, double-stranded chains propagating along [10[Formula: see text]] are formed via pairs of O-H⋯S and N-H⋯S hydrogen bonds. The chains are further stabilized by C-H⋯S interactions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶). For related structures, see: Choi et al. (2008 ▶). For the biological activity and pharmacological properties of thio­semi­carb­azones and their metal complexes, see: Cowley et al. (2002 ▶); Ming (2003 ▶); Lobana et al. (2004 ▶, 2007 ▶).

Experimental

Crystal data

C6H12N4OS

M = 188.26

Triclinic,

a = 5.5205 (1) Å

b = 8.6077 (2) Å

c = 9.5650 (2) Å

α = 79.750 (1)°

β = 89.509 (1)°

γ = 85.083 (1)°

V = 445.61 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.51 × 0.25 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.854, T max = 0.978

12035 measured reflections

3256 independent reflections

2920 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.08

3256 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053621/mw2038sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053621/mw2038Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053621/mw2038Isup3.cml

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

C6H12N4OS	Z = 2
Mr = 188.26	F(000) = 200
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Melting point = 487.5–490 K
a = 5.5205 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6077 (2) Å	Cell parameters from 7387 reflections
c = 9.5650 (2) Å	θ = 2.4–32.7°
α = 79.750 (1)°	µ = 0.32 mm−1
β = 89.509 (1)°	T = 100 K
γ = 85.083 (1)°	Plate, colourless
V = 445.61 (2) Å3	0.51 × 0.25 × 0.07 mm

Bruker APEXII CCD diffractometer	3256 independent reflections
Radiation source: fine-focus sealed tube	2920 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 32.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.854, Tmax = 0.978	k = −13→13
12035 measured reflections	l = −14→14

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0347P)2 + 0.1679P] where P = (Fo2 + 2Fc2)/3
3256 reflections	(Δ/σ)max = 0.001
124 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.39 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
S1	0.94334 (4)	0.16073 (3)	0.30007 (2)	0.01590 (7)
O1	−0.03857 (14)	0.29827 (9)	0.95645 (8)	0.02032 (15)
N1	0.16712 (15)	0.21630 (10)	0.90822 (9)	0.01569 (15)
N2	0.44402 (14)	0.22893 (9)	0.57941 (8)	0.01351 (14)
N3	0.64505 (15)	0.16555 (10)	0.51705 (8)	0.01452 (15)
N4	0.51169 (15)	0.32555 (10)	0.31045 (8)	0.01554 (15)
C1	0.02246 (18)	0.37515 (12)	0.67902 (10)	0.01835 (18)
H1A	−0.1458	0.3575	0.7064	0.028*
H1B	0.0464	0.3628	0.5798	0.028*
H1C	0.0556	0.4825	0.6895	0.028*
C2	0.19230 (17)	0.25693 (11)	0.77265 (10)	0.01371 (16)
C3	0.40835 (17)	0.17983 (11)	0.71298 (10)	0.01444 (16)
C4	0.5672 (2)	0.05499 (14)	0.80647 (11)	0.0258 (2)
H4A	0.6119	−0.0328	0.7560	0.039*
H4B	0.4791	0.0158	0.8932	0.039*
H4C	0.7146	0.1001	0.8314	0.039*
C5	0.68449 (17)	0.22272 (10)	0.37711 (9)	0.01296 (15)
C6	0.51377 (18)	0.39340 (12)	0.15976 (10)	0.01718 (18)
H6A	0.3703	0.4686	0.1362	0.026*
H6B	0.5111	0.3086	0.1038	0.026*
H6C	0.6612	0.4486	0.1379	0.026*
H1N3	0.754 (3)	0.0948 (18)	0.5626 (16)	0.025 (4)*
H1N4	0.387 (3)	0.3399 (18)	0.3605 (17)	0.026 (4)*
H1O1	−0.040 (3)	0.263 (2)	1.046 (2)	0.039 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01340 (11)	0.02020 (11)	0.01157 (10)	0.00444 (8)	0.00346 (7)	0.00102 (7)
O1	0.0191 (3)	0.0277 (4)	0.0116 (3)	0.0092 (3)	0.0044 (3)	−0.0022 (3)
N1	0.0146 (4)	0.0190 (3)	0.0124 (3)	0.0039 (3)	0.0031 (3)	−0.0025 (3)
N2	0.0128 (3)	0.0160 (3)	0.0112 (3)	0.0009 (3)	0.0029 (3)	−0.0020 (3)
N3	0.0135 (3)	0.0179 (3)	0.0102 (3)	0.0041 (3)	0.0024 (3)	0.0002 (3)
N4	0.0135 (4)	0.0203 (4)	0.0103 (3)	0.0044 (3)	0.0026 (3)	0.0012 (3)
C1	0.0175 (4)	0.0223 (4)	0.0126 (4)	0.0057 (3)	0.0007 (3)	0.0005 (3)
C2	0.0134 (4)	0.0154 (4)	0.0113 (4)	0.0017 (3)	0.0009 (3)	−0.0013 (3)
C3	0.0151 (4)	0.0161 (4)	0.0107 (4)	0.0028 (3)	0.0019 (3)	−0.0006 (3)
C4	0.0265 (5)	0.0314 (5)	0.0129 (4)	0.0159 (4)	0.0054 (4)	0.0048 (4)
C5	0.0129 (4)	0.0145 (4)	0.0108 (4)	0.0004 (3)	0.0014 (3)	−0.0014 (3)
C6	0.0180 (4)	0.0202 (4)	0.0106 (4)	0.0046 (3)	0.0013 (3)	0.0017 (3)

S1—C5	1.6914 (9)	C1—H1A	0.9800
O1—N1	1.4034 (10)	C1—H1B	0.9800
O1—H1O1	0.858 (19)	C1—H1C	0.9800
N1—C2	1.2911 (12)	C2—C3	1.4752 (13)
N2—C3	1.2912 (12)	C3—C4	1.4944 (13)
N2—N3	1.3733 (11)	C4—H4A	0.9800
N3—C5	1.3639 (12)	C4—H4B	0.9800
N3—H1N3	0.876 (15)	C4—H4C	0.9800
N4—C5	1.3285 (12)	C6—H6A	0.9800
N4—C6	1.4560 (12)	C6—H6B	0.9800
N4—H1N4	0.847 (16)	C6—H6C	0.9800
C1—C2	1.4977 (13)
N1—O1—H1O1	104.1 (12)	N2—C3—C2	115.15 (8)
C2—N1—O1	111.22 (8)	N2—C3—C4	125.00 (9)
C3—N2—N3	118.54 (8)	C2—C3—C4	119.84 (8)
C5—N3—N2	117.75 (8)	C3—C4—H4A	109.5
C5—N3—H1N3	118.0 (10)	C3—C4—H4B	109.5
N2—N3—H1N3	124.1 (10)	H4A—C4—H4B	109.5
C5—N4—C6	124.53 (8)	C3—C4—H4C	109.5
C5—N4—H1N4	114.1 (11)	H4A—C4—H4C	109.5
C6—N4—H1N4	120.9 (11)	H4B—C4—H4C	109.5
C2—C1—H1A	109.5	N4—C5—N3	116.23 (8)
C2—C1—H1B	109.5	N4—C5—S1	124.44 (7)
H1A—C1—H1B	109.5	N3—C5—S1	119.33 (7)
C2—C1—H1C	109.5	N4—C6—H6A	109.5
H1A—C1—H1C	109.5	N4—C6—H6B	109.5
H1B—C1—H1C	109.5	H6A—C6—H6B	109.5
N1—C2—C3	115.02 (8)	N4—C6—H6C	109.5
N1—C2—C1	124.30 (8)	H6A—C6—H6C	109.5
C3—C2—C1	120.68 (8)	H6B—C6—H6C	109.5
C3—N2—N3—C5	−177.76 (8)	N1—C2—C3—C4	4.82 (14)
O1—N1—C2—C3	178.35 (8)	C1—C2—C3—C4	−176.26 (10)
O1—N1—C2—C1	−0.52 (13)	C6—N4—C5—N3	−176.61 (9)
N3—N2—C3—C2	178.38 (8)	C6—N4—C5—S1	3.43 (14)
N3—N2—C3—C4	−1.47 (15)	N2—N3—C5—N4	−5.71 (13)
N1—C2—C3—N2	−175.03 (9)	N2—N3—C5—S1	174.25 (6)
C1—C2—C3—N2	3.88 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···S1i	0.877 (16)	2.781 (16)	3.6519 (9)	172.0 (14)
N4—H1N4···N2	0.848 (16)	2.155 (16)	2.5932 (11)	111.9 (13)
O1—H1O1···S1ii	0.857 (19)	2.437 (19)	3.2930 (8)	178.3 (17)
C1—H1B···N2	0.98	2.39	2.7919 (13)	104
C4—H4A···S1i	0.98	2.69	3.3991 (12)	129
C4—H4B···N1	0.98	2.35	2.7698 (14)	105
C4—H4C···O1iii	0.98	2.71	3.6173 (16)	154
C6—H6A···O1iv	0.98	2.63	3.6011 (12)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯S1i	0.877 (16)	2.781 (16)	3.6519 (9)	172.0 (14)
N4—H1N4⋯N2	0.848 (16)	2.155 (16)	2.5932 (11)	111.9 (13)
O1—H1O1⋯S1ii	0.857 (19)	2.437 (19)	3.2930 (8)	178.3 (17)
C4—H4A⋯S1i	0.98	2.69	3.3991 (12)	129

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