4-Ethyl-1-(4-meth-oxy-benzyl-idene)thio-semicarbazide.

In the title compound, C(11)H(15)N(3)OS, the dihedral angle between the aromatic ring and the thio-urea unit is 4.28 (7)° and an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring. In the crystal, mol-ecules are linked into (001) sheets by N-H⋯S hydrogen bonds.

Related literature

For background to the reactions and properties of thio­semicarbazones, see: Casas et al. (2000 ▶); Lobana et al. (2009 ▶); Quiroga & Ranninger (2004 ▶). For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C11H15N3OS

M = 237.32

Orthorhombic,

a = 13.066 (3) Å

b = 10.128 (2) Å

c = 19.224 (4) Å

V = 2543.9 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

22633 measured reflections

2912 independent reflections

2302 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.160

S = 1.05

2912 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.26 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/S1600536810022919/hb5492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022919/hb5492Isup2.hkl

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

C11H15N3OS	F(000) = 1008
Mr = 237.32	Dx = 1.239 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2302 reflections
a = 13.066 (3) Å	θ = 2.8–25.3°
b = 10.128 (2) Å	µ = 0.24 mm−1
c = 19.224 (4) Å	T = 293 K
V = 2543.9 (9) Å3	Block, colorless
Z = 8	0.22 × 0.20 × 0.18 mm

Bruker SMART CCD diffractometer	2302 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 27.5°, θmin = 3.1°
phi and ω scans	h = −16→16
22633 measured reflections	k = −13→13
2912 independent reflections	l = −24→24

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0997P)2 + 0.2868P] where P = (Fo2 + 2Fc2)/3
2912 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.26 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	0.12047 (4)	1.04218 (4)	0.57631 (3)	0.0768 (2)
N1	0.09565 (11)	0.83299 (14)	0.49802 (8)	0.0648 (4)
H1A	0.0548	0.8818	0.4742	0.078*
N2	0.11117 (10)	0.70368 (14)	0.47913 (8)	0.0598 (3)
C9	0.12596 (13)	0.30355 (18)	0.41061 (9)	0.0637 (4)
H9A	0.1545	0.2367	0.4375	0.076*
C3	0.14420 (12)	0.88334 (15)	0.55374 (9)	0.0596 (4)
N3	0.21067 (12)	0.80566 (14)	0.58550 (9)	0.0719 (4)
H3A	0.2271	0.7331	0.5651	0.086*
O1	0.09603 (11)	0.15651 (14)	0.31258 (7)	0.0803 (4)
C5	0.07418 (12)	0.53144 (16)	0.39807 (8)	0.0576 (4)
C10	0.11699 (13)	0.42999 (18)	0.43678 (9)	0.0621 (4)
H10A	0.1403	0.4476	0.4815	0.075*
C4	0.06596 (13)	0.66625 (17)	0.42425 (9)	0.0626 (4)
H4A	0.0262	0.7267	0.3999	0.075*
C8	0.09189 (12)	0.27751 (17)	0.34373 (9)	0.0621 (4)
C6	0.04087 (15)	0.5032 (2)	0.33114 (10)	0.0719 (5)
H6A	0.0115	0.5696	0.3044	0.086*
C11	0.14227 (19)	0.05082 (19)	0.34942 (13)	0.0866 (6)
H11A	0.1397	−0.0278	0.3216	0.130*
H11B	0.1061	0.0363	0.3922	0.130*
H11C	0.2123	0.0725	0.3594	0.130*
C2	0.25846 (16)	0.8338 (2)	0.65277 (13)	0.0910 (7)
H2B	0.2628	0.9285	0.6594	0.109*
H2C	0.3275	0.7984	0.6532	0.109*
C7	0.05071 (16)	0.3784 (2)	0.30398 (10)	0.0769 (5)
H7A	0.0296	0.3616	0.2586	0.092*
C1	0.1984 (3)	0.7743 (4)	0.71090 (15)	0.1455 (13)
H1B	0.2311	0.7943	0.7544	0.218*
H1C	0.1952	0.6803	0.7049	0.218*
H1D	0.1304	0.8100	0.7108	0.218*

	U11	U22	U33	U12	U13	U23
S1	0.0653 (3)	0.0441 (3)	0.1211 (5)	0.00297 (16)	−0.0100 (2)	−0.0109 (2)
N1	0.0687 (8)	0.0469 (7)	0.0786 (9)	0.0078 (6)	−0.0085 (7)	0.0005 (6)
N2	0.0596 (7)	0.0479 (7)	0.0720 (8)	0.0022 (5)	−0.0015 (6)	−0.0004 (6)
C9	0.0672 (9)	0.0567 (10)	0.0673 (9)	0.0013 (7)	−0.0052 (7)	0.0071 (7)
C3	0.0526 (7)	0.0447 (8)	0.0814 (10)	−0.0024 (6)	0.0014 (7)	−0.0002 (7)
N3	0.0716 (9)	0.0512 (8)	0.0929 (10)	0.0102 (6)	−0.0169 (8)	−0.0137 (7)
O1	0.0857 (8)	0.0647 (8)	0.0905 (9)	0.0036 (6)	−0.0126 (7)	−0.0171 (7)
C5	0.0515 (8)	0.0583 (9)	0.0632 (8)	0.0022 (6)	−0.0032 (6)	−0.0007 (6)
C10	0.0695 (10)	0.0594 (10)	0.0575 (8)	−0.0005 (7)	−0.0070 (7)	0.0017 (7)
C4	0.0604 (9)	0.0585 (9)	0.0688 (9)	0.0067 (7)	−0.0063 (7)	0.0016 (7)
C8	0.0547 (8)	0.0613 (10)	0.0702 (9)	−0.0008 (7)	−0.0022 (7)	−0.0071 (7)
C6	0.0762 (11)	0.0698 (10)	0.0697 (10)	0.0143 (9)	−0.0188 (8)	0.0012 (8)
C11	0.0946 (14)	0.0568 (11)	0.1083 (16)	0.0024 (9)	0.0065 (13)	−0.0021 (10)
C2	0.0766 (12)	0.0677 (12)	0.1285 (18)	0.0107 (9)	−0.0402 (13)	−0.0265 (11)
C7	0.0856 (12)	0.0772 (12)	0.0679 (10)	0.0109 (9)	−0.0231 (9)	−0.0102 (9)
C1	0.120 (2)	0.232 (4)	0.0849 (16)	−0.025 (2)	−0.0161 (16)	−0.032 (2)

S1—C3	1.6948 (17)	C10—H10A	0.9300
N1—C3	1.345 (2)	C4—H4A	0.9300
N1—N2	1.3742 (19)	C8—C7	1.385 (3)
N1—H1A	0.8600	C6—C7	1.373 (3)
N2—C4	1.267 (2)	C6—H6A	0.9300
C9—C10	1.381 (2)	C11—H11A	0.9600
C9—C8	1.386 (3)	C11—H11B	0.9600
C9—H9A	0.9300	C11—H11C	0.9600
C3—N3	1.321 (2)	C2—C1	1.492 (4)
N3—C2	1.464 (2)	C2—H2B	0.9700
N3—H3A	0.8600	C2—H2C	0.9700
O1—C8	1.365 (2)	C7—H7A	0.9300
O1—C11	1.419 (3)	C1—H1B	0.9600
C5—C10	1.387 (2)	C1—H1C	0.9600
C5—C6	1.388 (2)	C1—H1D	0.9600
C5—C4	1.459 (2)
C3—N1—N2	120.14 (13)	C7—C8—C9	119.75 (16)
C3—N1—H1A	119.9	C7—C6—C5	120.86 (16)
N2—N1—H1A	119.9	C7—C6—H6A	119.6
C4—N2—N1	115.87 (14)	C5—C6—H6A	119.6
C10—C9—C8	119.16 (16)	O1—C11—H11A	109.5
C10—C9—H9A	120.4	O1—C11—H11B	109.5
C8—C9—H9A	120.4	H11A—C11—H11B	109.5
N3—C3—N1	116.89 (14)	O1—C11—H11C	109.5
N3—C3—S1	124.54 (13)	H11A—C11—H11C	109.5
N1—C3—S1	118.51 (12)	H11B—C11—H11C	109.5
C3—N3—C2	124.95 (15)	N3—C2—C1	111.03 (19)
C3—N3—H3A	117.5	N3—C2—H2B	109.4
C2—N3—H3A	117.5	C1—C2—H2B	109.4
C8—O1—C11	118.37 (16)	N3—C2—H2C	109.4
C10—C5—C6	118.11 (16)	C1—C2—H2C	109.4
C10—C5—C4	122.54 (15)	H2B—C2—H2C	108.0
C6—C5—C4	119.32 (15)	C6—C7—C8	120.37 (16)
C9—C10—C5	121.73 (16)	C6—C7—H7A	119.8
C9—C10—H10A	119.1	C8—C7—H7A	119.8
C5—C10—H10A	119.1	C2—C1—H1B	109.5
N2—C4—C5	122.20 (15)	C2—C1—H1C	109.5
N2—C4—H4A	118.9	H1B—C1—H1C	109.5
C5—C4—H4A	118.9	C2—C1—H1D	109.5
O1—C8—C7	115.83 (15)	H1B—C1—H1D	109.5
O1—C8—C9	124.41 (16)	H1C—C1—H1D	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.60	3.4080 (17)	156
N3—H3A···N2	0.86	2.26	2.634 (2)	106
N3—H3A···S1ii	0.86	2.78	3.4670 (17)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.60	3.4080 (17)	156
N3—H3A⋯N2	0.86	2.26	2.634 (2)	106
N3—H3A⋯S1ii	0.86	2.78	3.4670 (17)	137

Symmetry codes: (i) ; (ii) .