(E)-N'-[1-(Thio-phen-2-yl)ethyl-idene]benzohydrazide.

The title compound, C(13)H(12)N(2)OS, was obtained from the condensation reaction of 2-acetyl-thio-phene and benzohydrazide. In the mol-ecule, the formohydrazide fragment is approximately planar (r.m.s deviation = 0.0146 Å) and the mean plane is oriented at dihedral angles of 24.47 (11) and 28.86 (13)°, respectively, to the phenyl and thio-phene rings. The thio-phene and phenyl rings make a dihedral angle of 53.21 (8)°. The benzamide fragment and thio-phene ring are located on the opposite sides of the C=N bond, showing an E conformation. Classical inter-molecular N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions are present in the crystal structure: three such bonds occur to the same O-atom acceptor.

Related literature

For applications of hydrazone derivatives in the biological field, see: Okabe et al. (1993 ▶). For general background to this work, see: Qiang et al. (2007 ▶). For a related structures, see: Xia et al. (2009 ▶); Shan et al. (2011 ▶)

Experimental

Crystal data

C13H12N2OS

M = 244.31

Orthorhombic,

a = 9.906 (3) Å

b = 10.542 (5) Å

c = 22.870 (5) Å

V = 2388.3 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 294 K

0.32 × 0.29 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

7859 measured reflections

2153 independent reflections

1552 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.101

S = 1.03

2153 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033101/xu6116sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033101/xu6116Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033101/xu6116Isup3.cml

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

C13H12N2OS	F(000) = 1024
Mr = 244.31	Dx = 1.359 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2153 reflections
a = 9.906 (3) Å	θ = 3.3–25.2°
b = 10.542 (5) Å	µ = 0.26 mm−1
c = 22.870 (5) Å	T = 294 K
V = 2388.3 (14) Å3	Block, yellow
Z = 8	0.32 × 0.29 × 0.28 mm

Rigaku R-AXIS RAPID IP diffractometer	1552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 25.2°, θmin = 3.3°
Detector resolution: 10.0 pixels mm-1	h = −10→11
ω scans	k = −11→12
7859 measured reflections	l = −27→23
2153 independent reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.4798P] where P = (Fo2 + 2Fc2)/3
2153 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.17 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	0.61206 (5)	0.31374 (5)	0.02223 (3)	0.0507 (2)
N1	0.30582 (15)	0.50999 (16)	0.12073 (8)	0.0425 (5)
H1	0.3095	0.5895	0.1290	0.051*
N2	0.41317 (15)	0.45043 (16)	0.09296 (8)	0.0422 (4)
O1	0.19122 (15)	0.32660 (14)	0.12656 (9)	0.0679 (5)
C1	0.08229 (18)	0.51074 (18)	0.16290 (10)	0.0376 (5)
C2	0.0570 (2)	0.6393 (2)	0.15591 (10)	0.0462 (6)
H2	0.1126	0.6881	0.1321	0.055*
C3	−0.0508 (2)	0.6949 (2)	0.18432 (11)	0.0549 (6)
H3	−0.0675	0.7810	0.1794	0.066*
C4	−0.1335 (2)	0.6245 (3)	0.21977 (11)	0.0583 (7)
H4	−0.2050	0.6629	0.2393	0.070*
C5	−0.1101 (2)	0.4972 (2)	0.22631 (12)	0.0606 (7)
H5	−0.1664	0.4490	0.2501	0.073*
C6	−0.0040 (2)	0.4405 (2)	0.19801 (10)	0.0495 (6)
H6	0.0103	0.3538	0.2024	0.059*
C7	0.19588 (19)	0.4411 (2)	0.13447 (10)	0.0423 (5)
C8	0.5283 (2)	0.50629 (18)	0.09602 (10)	0.0377 (5)
C9	0.63941 (18)	0.44513 (18)	0.06501 (9)	0.0377 (5)
C10	0.7727 (2)	0.4768 (2)	0.06465 (11)	0.0488 (6)
H10	0.8080	0.5451	0.0853	0.059*
C11	0.8514 (2)	0.3953 (2)	0.02980 (11)	0.0549 (7)
H11	0.9441	0.4043	0.0249	0.066*
C12	0.7782 (2)	0.3029 (2)	0.00428 (11)	0.0509 (6)
H12	0.8141	0.2409	−0.0201	0.061*
C13	0.5569 (2)	0.6255 (2)	0.12900 (11)	0.0523 (6)
H13A	0.5023	0.6930	0.1137	0.078*
H13B	0.6506	0.6471	0.1249	0.078*
H13C	0.5362	0.6130	0.1696	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.0387 (3)	0.0543 (4)	0.0590 (4)	−0.0030 (3)	−0.0008 (3)	−0.0143 (3)
N1	0.0321 (9)	0.0425 (9)	0.0529 (13)	0.0001 (8)	0.0042 (8)	−0.0043 (8)
N2	0.0328 (9)	0.0455 (9)	0.0484 (12)	0.0030 (8)	0.0026 (8)	−0.0031 (8)
O1	0.0465 (9)	0.0458 (9)	0.1112 (16)	−0.0032 (7)	0.0204 (9)	−0.0110 (9)
C1	0.0319 (10)	0.0441 (11)	0.0368 (13)	−0.0032 (9)	−0.0021 (9)	−0.0031 (9)
C2	0.0422 (12)	0.0472 (12)	0.0491 (16)	−0.0032 (10)	0.0022 (11)	0.0017 (10)
C3	0.0555 (14)	0.0501 (13)	0.0591 (17)	0.0100 (11)	0.0014 (12)	−0.0064 (12)
C4	0.0485 (13)	0.0730 (17)	0.0533 (17)	0.0060 (13)	0.0099 (12)	−0.0136 (13)
C5	0.0592 (15)	0.0688 (16)	0.0538 (18)	−0.0099 (13)	0.0207 (13)	−0.0064 (12)
C6	0.0537 (13)	0.0479 (12)	0.0470 (15)	−0.0034 (11)	0.0064 (11)	−0.0016 (11)
C7	0.0344 (11)	0.0441 (12)	0.0485 (15)	−0.0015 (10)	−0.0023 (10)	−0.0020 (10)
C8	0.0345 (10)	0.0393 (10)	0.0392 (13)	0.0005 (9)	−0.0022 (10)	0.0023 (9)
C9	0.0346 (10)	0.0382 (10)	0.0402 (13)	0.0003 (9)	−0.0007 (9)	0.0029 (9)
C10	0.0375 (11)	0.0448 (12)	0.0641 (17)	−0.0057 (10)	0.0032 (11)	−0.0064 (11)
C11	0.0354 (11)	0.0549 (13)	0.0744 (19)	0.0005 (10)	0.0097 (12)	−0.0043 (13)
C12	0.0437 (12)	0.0548 (14)	0.0542 (16)	0.0068 (11)	0.0061 (11)	−0.0068 (12)
C13	0.0389 (11)	0.0533 (13)	0.0646 (18)	−0.0006 (10)	0.0028 (11)	−0.0126 (12)

S1—C12	1.700 (2)	C4—H4	0.9300
S1—C9	1.717 (2)	C5—C6	1.371 (3)
N1—C7	1.346 (2)	C5—H5	0.9300
N1—N2	1.389 (2)	C6—H6	0.9300
N1—H1	0.8600	C8—C9	1.459 (3)
N2—C8	1.286 (2)	C8—C13	1.493 (3)
O1—C7	1.222 (2)	C9—C10	1.361 (3)
C1—C6	1.387 (3)	C10—C11	1.407 (3)
C1—C2	1.388 (3)	C10—H10	0.9300
C1—C7	1.492 (3)	C11—C12	1.347 (3)
C2—C3	1.380 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.371 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.370 (3)	C13—H13C	0.9600
C12—S1—C9	92.23 (10)	O1—C7—C1	121.45 (18)
C7—N1—N2	118.85 (17)	N1—C7—C1	116.53 (18)
C7—N1—H1	120.6	N2—C8—C9	116.11 (18)
N2—N1—H1	120.6	N2—C8—C13	125.55 (19)
C8—N2—N1	116.57 (17)	C9—C8—C13	118.34 (17)
C6—C1—C2	118.51 (19)	C10—C9—C8	128.73 (19)
C6—C1—C7	117.01 (18)	C10—C9—S1	110.31 (16)
C2—C1—C7	124.48 (19)	C8—C9—S1	120.95 (14)
C3—C2—C1	120.0 (2)	C9—C10—C11	113.0 (2)
C3—C2—H2	120.0	C9—C10—H10	123.5
C1—C2—H2	120.0	C11—C10—H10	123.5
C4—C3—C2	120.7 (2)	C12—C11—C10	112.8 (2)
C4—C3—H3	119.6	C12—C11—H11	123.6
C2—C3—H3	119.6	C10—C11—H11	123.6
C5—C4—C3	119.6 (2)	C11—C12—S1	111.59 (17)
C5—C4—H4	120.2	C11—C12—H12	124.2
C3—C4—H4	120.2	S1—C12—H12	124.2
C4—C5—C6	120.3 (2)	C8—C13—H13A	109.5
C4—C5—H5	119.8	C8—C13—H13B	109.5
C6—C5—H5	119.8	H13A—C13—H13B	109.5
C5—C6—C1	120.8 (2)	C8—C13—H13C	109.5
C5—C6—H6	119.6	H13A—C13—H13C	109.5
C1—C6—H6	119.6	H13B—C13—H13C	109.5
O1—C7—N1	121.93 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.50	3.340 (3)	166
C2—H2···O1i	0.93	2.43	3.251 (3)	147
C13—H13A···O1i	0.96	2.40	3.246 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.50	3.340 (3)	166
C2—H2⋯O1i	0.93	2.43	3.251 (3)	147
C13—H13A⋯O1i	0.96	2.40	3.246 (3)	147

Symmetry code: (i) .