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

In the crystal structure of the title compound, C(7)H(14)N(4)OS, mol-ecules are linked through N-H⋯S and O-H⋯N hydrogen bonds and C-H⋯S interactions, forming chains propagating along [21-1].

Related literature

For related structures, see:Abduelftah et al. (2012a ▶,b ▶); Choi et al. (2008 ▶). For the biological activity and pharmacological properties of thio­semicarbazones and their metal complexes, see: Cowley et al. (2002 ▶); Ming (2003 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H14N4OS

M = 202.28

Triclinic,

a = 5.7065 (2) Å

b = 9.0632 (3) Å

c = 10.7109 (4) Å

α = 71.309 (1)°

β = 76.318 (1)°

γ = 86.420 (1)°

V = 509.80 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.57 × 0.20 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.854, T max = 0.979

15442 measured reflections

4093 independent reflections

3648 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.093

S = 1.08

4093 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.33 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/S1600536812028632/ng5276sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028632/ng5276Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028632/ng5276Isup3.cml

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

C7H14N4OS	Z = 2
Mr = 202.28	F(000) = 216
Triclinic, P1	Dx = 1.318 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7065 (2) Å	Cell parameters from 8235 reflections
b = 9.0632 (3) Å	θ = 3.6–35.1°
c = 10.7109 (4) Å	µ = 0.29 mm−1
α = 71.309 (1)°	T = 100 K
β = 76.318 (1)°	Plate, colourless
γ = 86.420 (1)°	0.57 × 0.20 × 0.07 mm
V = 509.80 (3) Å3

Bruker APEXII CCD diffractometer	4093 independent reflections
Radiation source: fine-focus sealed tube	3648 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 34.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.854, Tmax = 0.979	k = −14→14
15442 measured reflections	l = −16→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1608P] where P = (Fo2 + 2Fc2)/3
4093 reflections	(Δ/σ)max = 0.001
121 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.33 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	0.44242 (4)	0.52051 (3)	0.69791 (2)	0.02043 (7)
O1	1.61220 (13)	1.04092 (8)	0.11132 (7)	0.02309 (14)
H1O1	1.6452	1.0633	0.0256	0.035*
N1	1.41316 (13)	0.94009 (9)	0.15010 (7)	0.01695 (13)
N2	1.01528 (13)	0.74755 (9)	0.45088 (7)	0.01587 (13)
N3	0.81401 (13)	0.65358 (9)	0.50040 (7)	0.01734 (13)
H1N3	0.7419	0.6218	0.4504	0.021*
N4	0.82678 (13)	0.66298 (9)	0.71029 (7)	0.01754 (13)
H1N4	0.9652	0.7085	0.6662	0.021*
C1	1.41628 (18)	0.94145 (12)	0.37977 (9)	0.02285 (17)
H1A	1.5830	0.9797	0.3405	0.034*
H1B	1.4111	0.8518	0.4613	0.034*
H1C	1.3154	1.0244	0.4035	0.034*
C2	1.32385 (15)	0.89332 (10)	0.27889 (8)	0.01613 (14)
C3	1.11201 (15)	0.78830 (10)	0.32272 (8)	0.01645 (14)
C4	1.02391 (19)	0.73958 (13)	0.22066 (9)	0.0260 (2)
H4A	0.9612	0.6324	0.2616	0.039*
H4B	1.1576	0.7453	0.1425	0.039*
H4C	0.8953	0.8091	0.1911	0.039*
C5	0.70823 (14)	0.61747 (10)	0.63536 (8)	0.01525 (13)
C6	0.73697 (16)	0.63713 (11)	0.85512 (8)	0.01993 (15)
H6A	0.7165	0.5240	0.9036	0.024*
H6B	0.5777	0.6864	0.8714	0.024*
C7	0.91280 (18)	0.70594 (12)	0.90870 (10)	0.02417 (18)
H7A	0.8508	0.6882	1.0059	0.036*
H7B	0.9315	0.8181	0.8612	0.036*
H7C	1.0696	0.6559	0.8936	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.01501 (10)	0.03141 (12)	0.01420 (10)	−0.00775 (7)	0.00028 (6)	−0.00740 (8)
O1	0.0233 (3)	0.0273 (3)	0.0159 (3)	−0.0142 (2)	−0.0004 (2)	−0.0031 (2)
N1	0.0172 (3)	0.0177 (3)	0.0139 (3)	−0.0061 (2)	−0.0013 (2)	−0.0027 (2)
N2	0.0154 (3)	0.0189 (3)	0.0117 (3)	−0.0038 (2)	−0.0016 (2)	−0.0030 (2)
N3	0.0163 (3)	0.0242 (3)	0.0109 (3)	−0.0066 (2)	−0.0010 (2)	−0.0050 (2)
N4	0.0158 (3)	0.0247 (3)	0.0119 (3)	−0.0052 (2)	−0.0012 (2)	−0.0060 (2)
C1	0.0260 (4)	0.0279 (4)	0.0160 (4)	−0.0094 (3)	−0.0062 (3)	−0.0060 (3)
C2	0.0174 (3)	0.0173 (3)	0.0129 (3)	−0.0041 (2)	−0.0032 (2)	−0.0032 (3)
C3	0.0175 (3)	0.0197 (3)	0.0116 (3)	−0.0050 (3)	−0.0021 (2)	−0.0040 (3)
C4	0.0287 (4)	0.0360 (5)	0.0138 (3)	−0.0161 (4)	−0.0015 (3)	−0.0081 (3)
C5	0.0140 (3)	0.0191 (3)	0.0117 (3)	−0.0020 (2)	−0.0017 (2)	−0.0040 (3)
C6	0.0202 (3)	0.0278 (4)	0.0118 (3)	−0.0039 (3)	−0.0012 (3)	−0.0073 (3)
C7	0.0253 (4)	0.0323 (5)	0.0194 (4)	−0.0007 (3)	−0.0078 (3)	−0.0122 (3)

S1—C5	1.6823 (8)	C1—H1B	0.9800
O1—N1	1.4004 (9)	C1—H1C	0.9800
O1—H1O1	0.8499	C2—C3	1.4753 (11)
N1—C2	1.2891 (10)	C3—C4	1.4966 (12)
N2—C3	1.2913 (10)	C4—H4A	0.9800
N2—N3	1.3676 (10)	C4—H4B	0.9800
N3—C5	1.3674 (10)	C4—H4C	0.9800
N3—H1N3	0.8699	C6—C7	1.5182 (13)
N4—C5	1.3326 (10)	C6—H6A	0.9900
N4—C6	1.4594 (11)	C6—H6B	0.9900
N4—H1N4	0.8699	C7—H7A	0.9800
C1—C2	1.4955 (12)	C7—H7B	0.9800
C1—H1A	0.9800	C7—H7C	0.9800
N1—O1—H1O1	101.9	C3—C4—H4A	109.5
C2—N1—O1	113.41 (7)	C3—C4—H4B	109.5
C3—N2—N3	118.88 (7)	H4A—C4—H4B	109.5
C5—N3—N2	117.92 (7)	C3—C4—H4C	109.5
C5—N3—H1N3	117.7	H4A—C4—H4C	109.5
N2—N3—H1N3	124.1	H4B—C4—H4C	109.5
C5—N4—C6	123.53 (7)	N4—C5—N3	116.43 (7)
C5—N4—H1N4	114.6	N4—C5—S1	123.74 (6)
C6—N4—H1N4	121.9	N3—C5—S1	119.83 (6)
C2—C1—H1A	109.5	N4—C6—C7	110.08 (7)
C2—C1—H1B	109.5	N4—C6—H6A	109.6
H1A—C1—H1B	109.5	C7—C6—H6A	109.6
C2—C1—H1C	109.5	N4—C6—H6B	109.6
H1A—C1—H1C	109.5	C7—C6—H6B	109.6
H1B—C1—H1C	109.5	H6A—C6—H6B	108.2
N1—C2—C3	114.67 (7)	C6—C7—H7A	109.5
N1—C2—C1	124.68 (7)	C6—C7—H7B	109.5
C3—C2—C1	120.63 (7)	H7A—C7—H7B	109.5
N2—C3—C2	114.69 (7)	C6—C7—H7C	109.5
N2—C3—C4	125.37 (8)	H7A—C7—H7C	109.5
C2—C3—C4	119.93 (7)	H7B—C7—H7C	109.5
C3—N2—N3—C5	−177.16 (8)	N1—C2—C3—C4	2.37 (13)
O1—N1—C2—C3	179.32 (7)	C1—C2—C3—C4	−179.18 (9)
O1—N1—C2—C1	0.93 (13)	C6—N4—C5—N3	178.54 (8)
N3—N2—C3—C2	178.30 (7)	C6—N4—C5—S1	−1.47 (13)
N3—N2—C3—C4	−0.76 (14)	N2—N3—C5—N4	−7.33 (12)
N1—C2—C3—N2	−176.75 (8)	N2—N3—C5—S1	172.68 (6)
C1—C2—C3—N2	1.71 (12)	C5—N4—C6—C7	−178.86 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1i	0.85	2.00	2.7876 (10)	154
N3—H1N3···S1ii	0.87	2.75	3.6124 (8)	171
N4—H1N4···N2	0.87	2.17	2.6055 (10)	111
C1—H1A···O1	0.98	2.30	2.6970 (11)	103
C4—H4A···S1ii	0.98	2.64	3.4302 (12)	138
C4—H4B···N1	0.98	2.39	2.7636 (14)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1i	0.85	2.00	2.7876 (10)	154
N3—H1N3⋯S1ii	0.87	2.75	3.6124 (8)	171
C4—H4A⋯S1ii	0.98	2.64	3.4302 (12)	138

Symmetry codes: (i) ; (ii) .