4-Ethyl-1-(4-methyl-benzyl-idene)thio-semicarbazide.

In the title compound, C(11)H(15)N(3)S, an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring. In the crystal, inversion dimers linked by pairs of N-H⋯S bonds occur, generating an R(2) (2)(8) loop.

Related literature

For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C11H15N3S

M = 221.32

Monoclinic,

a = 8.5777 (17) Å

b = 13.620 (3) Å

c = 10.364 (2) Å

β = 90.00 (3)°

V = 1210.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.23 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

11225 measured reflections

2724 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.144

S = 1.10

2724 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 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/S1600536810017988/hb5448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017988/hb5448Isup2.hkl

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

C11H15N3S	F(000) = 472
Mr = 221.32	Dx = 1.214 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1811 reflections
a = 8.5777 (17) Å	θ = 3.7–25.4°
b = 13.620 (3) Å	µ = 0.24 mm−1
c = 10.364 (2) Å	T = 293 K
β = 90.00 (3)°	Block, colorless
V = 1210.8 (4) Å3	0.23 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1811 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 27.5°, θmin = 3.4°
phi and ω scans	h = −10→11
11225 measured reflections	k = −17→17
2724 independent reflections	l = −13→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0722P)2 + 0.0957P] where P = (Fo2 + 2Fc2)/3
2724 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.18659 (7)	0.61350 (4)	0.05705 (5)	0.0646 (2)
N2	0.02730 (19)	0.59199 (13)	−0.15745 (14)	0.0517 (4)
H2A	−0.0314	0.5527	−0.1144	0.062*
N1	−0.00273 (18)	0.61045 (12)	−0.28521 (14)	0.0471 (4)
C5	−0.1597 (2)	0.57835 (14)	−0.47004 (17)	0.0454 (4)
C6	−0.0800 (2)	0.64307 (15)	−0.55008 (18)	0.0514 (5)
H6A	0.0041	0.6785	−0.5179	0.062*
C8	−0.2494 (2)	0.60447 (16)	−0.72820 (18)	0.0535 (5)
C4	−0.1162 (2)	0.56386 (15)	−0.33565 (18)	0.0494 (5)
H4A	−0.1724	0.5196	−0.2855	0.059*
C3	0.1500 (2)	0.63616 (15)	−0.09996 (17)	0.0486 (5)
N3	0.2320 (2)	0.69703 (14)	−0.17353 (16)	0.0586 (5)
H3A	0.1966	0.7095	−0.2494	0.070*
C7	−0.1245 (2)	0.65502 (17)	−0.67644 (18)	0.0556 (5)
H7A	−0.0691	0.6983	−0.7285	0.067*
C10	−0.2838 (2)	0.52628 (17)	−0.52182 (19)	0.0582 (5)
H10A	−0.3384	0.4819	−0.4706	0.070*
C9	−0.3270 (2)	0.53994 (18)	−0.6490 (2)	0.0618 (6)
H9A	−0.4107	0.5045	−0.6819	0.074*
C11	−0.2989 (3)	0.6213 (2)	−0.8660 (2)	0.0747 (7)
H11A	−0.3868	0.5803	−0.8857	0.112*
H11B	−0.2142	0.6054	−0.9228	0.112*
H11C	−0.3272	0.6890	−0.8774	0.112*
C2	0.3779 (3)	0.7445 (2)	−0.1356 (2)	0.0759 (7)
H2B	0.3760	0.7574	−0.0436	0.091*
H2C	0.3869	0.8071	−0.1798	0.091*
C1	0.5171 (3)	0.6822 (2)	−0.1673 (3)	0.0875 (9)
H1B	0.6104	0.7152	−0.1403	0.131*
H1C	0.5210	0.6710	−0.2587	0.131*
H1D	0.5089	0.6204	−0.1232	0.131*

	U11	U22	U33	U12	U13	U23
S1	0.0854 (4)	0.0693 (4)	0.0392 (3)	−0.0124 (3)	−0.0082 (2)	0.0033 (2)
N2	0.0574 (10)	0.0600 (11)	0.0377 (8)	−0.0058 (8)	−0.0014 (7)	0.0049 (7)
N1	0.0559 (9)	0.0484 (9)	0.0372 (8)	0.0019 (7)	−0.0015 (7)	0.0003 (6)
C5	0.0449 (10)	0.0467 (11)	0.0445 (9)	0.0024 (8)	−0.0011 (7)	−0.0003 (7)
C6	0.0552 (11)	0.0497 (11)	0.0493 (10)	−0.0063 (9)	−0.0042 (8)	0.0026 (8)
C8	0.0596 (12)	0.0557 (12)	0.0451 (10)	0.0138 (10)	−0.0061 (9)	−0.0064 (8)
C4	0.0509 (11)	0.0510 (12)	0.0463 (10)	−0.0008 (9)	0.0016 (8)	0.0047 (8)
C3	0.0561 (11)	0.0490 (11)	0.0406 (9)	0.0019 (9)	−0.0004 (8)	−0.0009 (8)
N3	0.0645 (10)	0.0658 (11)	0.0455 (8)	−0.0144 (9)	−0.0061 (7)	0.0078 (7)
C7	0.0654 (12)	0.0525 (12)	0.0488 (10)	0.0008 (10)	0.0009 (9)	0.0059 (8)
C10	0.0551 (11)	0.0631 (14)	0.0563 (11)	−0.0121 (10)	−0.0008 (9)	0.0036 (9)
C9	0.0572 (12)	0.0670 (15)	0.0611 (12)	−0.0059 (10)	−0.0120 (10)	−0.0078 (10)
C11	0.0885 (16)	0.0861 (19)	0.0494 (12)	0.0190 (14)	−0.0140 (11)	−0.0061 (11)
C2	0.0977 (18)	0.0733 (17)	0.0569 (13)	−0.0359 (15)	−0.0120 (12)	0.0062 (11)
C1	0.0677 (16)	0.095 (2)	0.099 (2)	−0.0246 (15)	−0.0174 (14)	0.0220 (15)

S1—C3	1.6858 (18)	N3—C2	1.462 (3)
N2—C3	1.351 (2)	N3—H3A	0.8600
N2—N1	1.372 (2)	C7—H7A	0.9300
N2—H2A	0.8600	C10—C9	1.381 (3)
N1—C4	1.274 (2)	C10—H10A	0.9300
C5—C10	1.388 (3)	C9—H9A	0.9300
C5—C6	1.390 (3)	C11—H11A	0.9600
C5—C4	1.455 (2)	C11—H11B	0.9600
C6—C7	1.374 (3)	C11—H11C	0.9600
C6—H6A	0.9300	C2—C1	1.502 (4)
C8—C9	1.375 (3)	C2—H2B	0.9700
C8—C7	1.381 (3)	C2—H2C	0.9700
C8—C11	1.508 (3)	C1—H1B	0.9600
C4—H4A	0.9300	C1—H1C	0.9600
C3—N3	1.328 (3)	C1—H1D	0.9600
C3—N2—N1	119.36 (16)	C9—C10—C5	120.4 (2)
C3—N2—H2A	120.3	C9—C10—H10A	119.8
N1—N2—H2A	120.3	C5—C10—H10A	119.8
C4—N1—N2	116.63 (16)	C8—C9—C10	121.75 (19)
C10—C5—C6	118.08 (17)	C8—C9—H9A	119.1
C10—C5—C4	119.85 (18)	C10—C9—H9A	119.1
C6—C5—C4	122.08 (17)	C8—C11—H11A	109.5
C7—C6—C5	120.48 (18)	C8—C11—H11B	109.5
C7—C6—H6A	119.8	H11A—C11—H11B	109.5
C5—C6—H6A	119.8	C8—C11—H11C	109.5
C9—C8—C7	117.52 (18)	H11A—C11—H11C	109.5
C9—C8—C11	121.8 (2)	H11B—C11—H11C	109.5
C7—C8—C11	120.7 (2)	N3—C2—C1	111.8 (2)
N1—C4—C5	121.40 (18)	N3—C2—H2B	109.3
N1—C4—H4A	119.3	C1—C2—H2B	109.3
C5—C4—H4A	119.3	N3—C2—H2C	109.3
N3—C3—N2	115.95 (16)	C1—C2—H2C	109.3
N3—C3—S1	124.73 (15)	H2B—C2—H2C	107.9
N2—C3—S1	119.30 (15)	C2—C1—H1B	109.5
C3—N3—C2	125.12 (17)	C2—C1—H1C	109.5
C3—N3—H3A	117.4	H1B—C1—H1C	109.5
C2—N3—H3A	117.4	C2—C1—H1D	109.5
C6—C7—C8	121.8 (2)	H1B—C1—H1D	109.5
C6—C7—H7A	119.1	H1C—C1—H1D	109.5
C8—C7—H7A	119.1

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.86	2.69	3.505 (2)	158
N3—H3A···N1	0.86	2.21	2.605 (2)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.86	2.69	3.505 (2)	158
N3—H3A⋯N1	0.86	2.21	2.605 (2)	108

Symmetry code: (i) .