1-(3,4-Dimethyl-benzyl-idene)-4-ethyl-thio-semicarbazide.

The title compound, C(12)H(17)N(3)S, was prepared by the reaction of 4-ethyl-thio-semicarbazide and 3,4-dimethyl-benzaldehyde. The dihedral angle between the thiourea unit and the benzene ring is 7.09 (8)°. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds occur.

Related literature

For applications of Schiff base compounds, see: Casas et al. (2000 ▶); Habermehl et al. (2006 ▶). For the structure of 4-ethyl-1-(4-methyl­benzyl­idene)thio­semicarbazide, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C12H17N3S

M = 235.35

Monoclinic,

a = 8.6659 (17) Å

b = 15.207 (3) Å

c = 9.993 (2) Å

β = 93.47 (3)°

V = 1314.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

12215 measured reflections

3006 independent reflections

2429 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.206

S = 1.05

3006 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810038389/lh5136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038389/lh5136Isup2.hkl

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

C12H17N3S	F(000) = 504
Mr = 235.35	Dx = 1.189 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2429 reflections
a = 8.6659 (17) Å	θ = 3.3–27.5°
b = 15.207 (3) Å	µ = 0.23 mm−1
c = 9.993 (2) Å	T = 293 K
β = 93.47 (3)°	Block, colorless
V = 1314.5 (5) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	2429 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
graphite	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −11→11
12215 measured reflections	k = −19→19
3006 independent reflections	l = −12→11

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1293P)2 + 0.2681P] where P = (Fo2 + 2Fc2)/3
3006 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.34 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	0.84996 (8)	0.11266 (4)	0.92188 (6)	0.0702 (3)
N1	1.02915 (18)	0.11306 (10)	1.28935 (16)	0.0480 (4)
N2	0.9879 (2)	0.08927 (11)	1.15935 (16)	0.0532 (4)
H2A	1.0235	0.0415	1.1269	0.064*
C9	1.1228 (2)	0.06157 (13)	1.35388 (19)	0.0513 (4)
H9A	1.1574	0.0115	1.3114	0.062*
N3	0.8377 (2)	0.21192 (12)	1.14109 (18)	0.0581 (4)
H3A	0.8630	0.2193	1.2249	0.070*
C4	1.1328 (3)	0.15253 (16)	1.5627 (2)	0.0597 (5)
H4A	1.0691	0.1947	1.5206	0.072*
C8	1.2782 (2)	0.01920 (13)	1.5576 (2)	0.0544 (5)
H8A	1.3120	−0.0293	1.5108	0.065*
C3	1.1773 (2)	0.07867 (13)	1.49181 (19)	0.0487 (4)
C10	0.8916 (2)	0.14075 (13)	1.08270 (19)	0.0485 (4)
C7	1.3299 (2)	0.03031 (14)	1.6911 (2)	0.0571 (5)
C6	1.2793 (3)	0.10241 (17)	1.7607 (2)	0.0644 (6)
C5	1.1829 (3)	0.16286 (18)	1.6946 (2)	0.0708 (6)
H5A	1.1511	0.2120	1.7409	0.085*
C2	1.4415 (3)	−0.0353 (2)	1.7562 (3)	0.0837 (8)
H2B	1.4651	−0.0188	1.8480	0.126*
H2C	1.5348	−0.0360	1.7092	0.126*
H2D	1.3956	−0.0927	1.7530	0.126*
C12	0.5844 (3)	0.2822 (2)	1.1272 (4)	0.0950 (9)
H12A	0.5239	0.3265	1.0800	0.143*
H12B	0.5935	0.2963	1.2210	0.143*
H12C	0.5348	0.2261	1.1149	0.143*
C11	0.7391 (3)	0.27866 (18)	1.0749 (3)	0.0787 (7)
H11A	0.7289	0.2663	0.9796	0.094*
H11B	0.7881	0.3357	1.0868	0.094*
C1	1.3292 (4)	0.1167 (3)	1.9069 (3)	0.0973 (11)
H1B	1.2832	0.1698	1.9380	0.146*
H1C	1.4397	0.1216	1.9166	0.146*
H1D	1.2962	0.0679	1.9589	0.146*

	U11	U22	U33	U12	U13	U23
S1	0.0834 (5)	0.0734 (4)	0.0509 (4)	0.0196 (3)	−0.0188 (3)	−0.0005 (2)
N1	0.0472 (8)	0.0524 (8)	0.0437 (8)	0.0018 (6)	−0.0027 (6)	0.0016 (6)
N2	0.0575 (9)	0.0541 (8)	0.0464 (8)	0.0123 (7)	−0.0088 (7)	−0.0005 (7)
C9	0.0536 (10)	0.0496 (9)	0.0496 (10)	0.0050 (7)	−0.0049 (8)	0.0006 (8)
N3	0.0575 (9)	0.0611 (10)	0.0554 (9)	0.0163 (8)	0.0018 (7)	0.0074 (7)
C4	0.0582 (11)	0.0668 (13)	0.0535 (11)	0.0141 (9)	−0.0015 (8)	−0.0024 (9)
C8	0.0552 (10)	0.0493 (9)	0.0572 (11)	−0.0028 (8)	−0.0075 (8)	0.0059 (8)
C3	0.0461 (9)	0.0515 (9)	0.0481 (9)	−0.0020 (7)	−0.0019 (7)	0.0045 (8)
C10	0.0414 (9)	0.0526 (9)	0.0510 (10)	0.0036 (7)	−0.0019 (7)	0.0086 (8)
C7	0.0505 (10)	0.0641 (11)	0.0554 (11)	−0.0114 (8)	−0.0088 (8)	0.0156 (9)
C6	0.0523 (11)	0.0943 (16)	0.0459 (11)	−0.0092 (10)	−0.0025 (8)	0.0010 (10)
C5	0.0677 (14)	0.0861 (16)	0.0580 (12)	0.0112 (11)	0.0003 (10)	−0.0162 (11)
C2	0.0802 (16)	0.0911 (18)	0.0768 (16)	0.0046 (13)	−0.0208 (13)	0.0262 (14)
C12	0.0636 (15)	0.0908 (19)	0.128 (3)	0.0270 (14)	−0.0117 (15)	−0.0062 (18)
C11	0.0817 (16)	0.0739 (15)	0.0810 (16)	0.0347 (13)	0.0081 (12)	0.0185 (12)
C1	0.089 (2)	0.150 (3)	0.0508 (14)	−0.0023 (18)	−0.0132 (13)	−0.0072 (15)

S1—C10	1.681 (2)	C7—C2	1.509 (3)
N1—C9	1.275 (2)	C6—C5	1.383 (3)
N1—N2	1.375 (2)	C6—C1	1.514 (3)
N2—C10	1.349 (2)	C5—H5A	0.9300
N2—H2A	0.8600	C2—H2B	0.9600
C9—C3	1.453 (3)	C2—H2C	0.9600
C9—H9A	0.9300	C2—H2D	0.9600
N3—C10	1.328 (3)	C12—C11	1.468 (4)
N3—C11	1.459 (3)	C12—H12A	0.9600
N3—H3A	0.8600	C12—H12B	0.9600
C4—C5	1.371 (3)	C12—H12C	0.9600
C4—C3	1.395 (3)	C11—H11A	0.9700
C4—H4A	0.9300	C11—H11B	0.9700
C8—C7	1.392 (3)	C1—H1B	0.9600
C8—C3	1.395 (3)	C1—H1C	0.9600
C8—H8A	0.9300	C1—H1D	0.9600
C7—C6	1.384 (3)
C9—N1—N2	115.95 (16)	C4—C5—C6	122.0 (2)
C10—N2—N1	120.03 (16)	C4—C5—H5A	119.0
C10—N2—H2A	120.0	C6—C5—H5A	119.0
N1—N2—H2A	120.0	C7—C2—H2B	109.5
N1—C9—C3	122.03 (18)	C7—C2—H2C	109.5
N1—C9—H9A	119.0	H2B—C2—H2C	109.5
C3—C9—H9A	119.0	C7—C2—H2D	109.5
C10—N3—C11	125.4 (2)	H2B—C2—H2D	109.5
C10—N3—H3A	117.3	H2C—C2—H2D	109.5
C11—N3—H3A	117.3	C11—C12—H12A	109.5
C5—C4—C3	119.9 (2)	C11—C12—H12B	109.5
C5—C4—H4A	120.0	H12A—C12—H12B	109.5
C3—C4—H4A	120.0	C11—C12—H12C	109.5
C7—C8—C3	121.9 (2)	H12A—C12—H12C	109.5
C7—C8—H8A	119.0	H12B—C12—H12C	109.5
C3—C8—H8A	119.0	N3—C11—C12	112.7 (2)
C8—C3—C4	117.90 (18)	N3—C11—H11A	109.0
C8—C3—C9	119.30 (18)	C12—C11—H11A	109.0
C4—C3—C9	122.80 (18)	N3—C11—H11B	109.0
N3—C10—N2	116.46 (17)	C12—C11—H11B	109.0
N3—C10—S1	124.51 (14)	H11A—C11—H11B	107.8
N2—C10—S1	119.02 (15)	C6—C1—H1B	109.5
C6—C7—C8	119.00 (19)	C6—C1—H1C	109.5
C6—C7—C2	121.4 (2)	H1B—C1—H1C	109.5
C8—C7—C2	119.6 (2)	C6—C1—H1D	109.5
C5—C6—C7	119.1 (2)	H1B—C1—H1D	109.5
C5—C6—C1	119.6 (2)	H1C—C1—H1D	109.5
C7—C6—C1	121.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.86	2.65	3.4929 (18)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.86	2.65	3.4929 (18)	168

Symmetry code: (i) .