N'-[1-(2-Hy-droxy-phen-yl)ethyl-idene]thio-phene-2-carbohydrazide.

The title compound, C(13)H(12)N(2)O(2)S, was prepared by the reaction of 1-(2-hy-droxy-phen-yl)ethanone and thio-phene-2-carbohydrazide. The dihedral angle between the benzene and thio-phene rings is 10.07 (17)°. An intra-molecular O-H⋯N hydrogen bond may influence the mol-ecular conformation. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains along [010].

Related literature

For applications of Schiff base compounds, see: Casas et al. (2000 ▶); Habermehl et al. (2006 ▶). For related structures, see: Li & Jian (2010 ▶); Li & Meng (2010 ▶).

Experimental

Crystal data

C13H12N2O2S

M = 260.31

Orthorhombic,

a = 13.454 (3) Å

b = 7.6303 (15) Å

c = 24.305 (5) Å

V = 2495.1 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.25 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer

16044 measured reflections

2189 independent reflections

1047 reflections with I > 2σ(I)

R int = 0.156

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.126

S = 0.89

2189 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.29 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/S1600536810050002/lh5171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050002/lh5171Isup2.hkl

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

C13H12N2O2S	F(000) = 1088
Mr = 260.31	Dx = 1.386 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2839 reflections
a = 13.454 (3) Å	θ = 3.0–27.5°
b = 7.6303 (15) Å	µ = 0.25 mm−1
c = 24.305 (5) Å	T = 293 K
V = 2495.1 (9) Å3	Block, colorless
Z = 8	0.25 × 0.20 × 0.19 mm

Bruker SMART CCD diffractometer	1047 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.156
graphite	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −16→14
16044 measured reflections	k = −9→9
2189 independent reflections	l = −28→28

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3
2189 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 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	0.44225 (8)	0.02138 (15)	0.75337 (5)	0.0783 (4)
O1	0.37088 (16)	0.2689 (3)	0.84114 (10)	0.0546 (7)
O2	0.31584 (19)	0.3541 (4)	0.98652 (13)	0.0591 (8)
N1	0.2282 (2)	0.1203 (4)	0.85835 (12)	0.0498 (8)
N2	0.2212 (2)	0.2088 (4)	0.90867 (12)	0.0491 (8)
C1	0.3999 (3)	−0.1057 (5)	0.70050 (16)	0.0698 (12)
H1	0.4408	−0.1542	0.6737	0.084*
C2	0.3020 (3)	−0.1273 (4)	0.70204 (15)	0.0562 (10)
H2A	0.2668	−0.1921	0.6761	0.067*
C3	0.2570 (3)	−0.0416 (4)	0.74723 (16)	0.0502 (9)
H3A	0.1891	−0.0430	0.7543	0.060*
C4	0.3251 (2)	0.0437 (4)	0.77919 (15)	0.0457 (9)
C5	0.3114 (3)	0.1538 (5)	0.82858 (14)	0.0462 (9)
C6	0.1375 (2)	0.2103 (4)	0.93416 (15)	0.0453 (9)
C7	0.0439 (2)	0.1341 (5)	0.91119 (16)	0.0632 (11)
H7A	0.0469	0.1355	0.8717	0.095*
H7B	−0.0119	0.2024	0.9233	0.095*
H7C	0.0366	0.0156	0.9238	0.095*
C8	0.1386 (2)	0.2934 (4)	0.98860 (14)	0.0421 (9)
C9	0.0523 (3)	0.3054 (4)	1.02020 (16)	0.0541 (10)
H9A	−0.0066	0.2609	1.0059	0.065*
C10	0.0510 (3)	0.3801 (5)	1.07136 (16)	0.0626 (11)
H10A	−0.0080	0.3859	1.0912	0.075*
C11	0.1374 (3)	0.4465 (5)	1.09333 (16)	0.0603 (11)
H11A	0.1368	0.4981	1.1280	0.072*
C12	0.2244 (3)	0.4366 (5)	1.06408 (16)	0.0571 (10)
H12A	0.2827	0.4812	1.0791	0.069*
C13	0.2261 (3)	0.3603 (4)	1.01196 (15)	0.0456 (9)
H1N	0.186 (3)	0.023 (5)	0.8545 (16)	0.082 (13)*
H2O	0.305 (3)	0.315 (6)	0.9561 (19)	0.094 (19)*

	U11	U22	U33	U12	U13	U23
S1	0.0552 (6)	0.0905 (8)	0.0893 (9)	−0.0020 (6)	0.0197 (6)	−0.0246 (7)
O1	0.0464 (15)	0.0593 (15)	0.0581 (17)	−0.0070 (12)	−0.0021 (12)	−0.0067 (13)
O2	0.0448 (16)	0.0713 (19)	0.061 (2)	−0.0090 (13)	0.0029 (15)	−0.0080 (16)
N1	0.0521 (19)	0.0515 (19)	0.046 (2)	−0.0051 (16)	0.0061 (15)	−0.0075 (17)
N2	0.0530 (19)	0.0485 (18)	0.046 (2)	−0.0035 (14)	0.0054 (15)	−0.0057 (16)
C1	0.085 (3)	0.063 (3)	0.061 (3)	0.003 (2)	0.019 (2)	−0.013 (2)
C2	0.074 (3)	0.044 (2)	0.051 (3)	0.006 (2)	0.004 (2)	−0.0002 (19)
C3	0.053 (2)	0.045 (2)	0.053 (2)	0.0025 (17)	0.008 (2)	0.004 (2)
C4	0.045 (2)	0.046 (2)	0.046 (2)	0.0064 (16)	0.0065 (17)	0.0029 (18)
C5	0.044 (2)	0.049 (2)	0.046 (2)	0.0054 (18)	−0.0015 (18)	0.0014 (19)
C6	0.042 (2)	0.045 (2)	0.050 (2)	−0.0035 (16)	−0.0012 (18)	0.0007 (18)
C7	0.054 (2)	0.068 (3)	0.068 (3)	−0.001 (2)	−0.003 (2)	−0.019 (2)
C8	0.043 (2)	0.044 (2)	0.038 (2)	−0.0019 (15)	0.0009 (17)	0.0021 (17)
C9	0.048 (2)	0.059 (3)	0.055 (3)	−0.0081 (18)	0.007 (2)	0.000 (2)
C10	0.062 (3)	0.075 (3)	0.051 (3)	0.000 (2)	0.015 (2)	0.005 (2)
C11	0.076 (3)	0.065 (3)	0.040 (2)	0.003 (2)	0.008 (2)	0.000 (2)
C12	0.062 (3)	0.056 (2)	0.053 (3)	−0.0039 (19)	−0.004 (2)	0.000 (2)
C13	0.047 (2)	0.041 (2)	0.049 (2)	0.0011 (17)	0.0033 (18)	0.0015 (19)

S1—C4	1.705 (3)	C6—C8	1.467 (5)
S1—C1	1.708 (4)	C6—C7	1.495 (4)
O1—C5	1.227 (4)	C7—H7A	0.9600
O2—C13	1.357 (4)	C7—H7B	0.9600
O2—H2O	0.81 (4)	C7—H7C	0.9600
N1—C5	1.356 (4)	C8—C9	1.395 (4)
N1—N2	1.400 (4)	C8—C13	1.402 (4)
N1—H1N	0.94 (4)	C9—C10	1.368 (5)
N2—C6	1.285 (4)	C9—H9A	0.9300
C1—C2	1.327 (5)	C10—C11	1.377 (5)
C1—H1	0.9300	C10—H10A	0.9300
C2—C3	1.415 (5)	C11—C12	1.371 (5)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.366 (5)	C12—C13	1.395 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.477 (5)
C4—S1—C1	91.4 (2)	C6—C7—H7A	109.5
C13—O2—H2O	105 (3)	C6—C7—H7B	109.5
C5—N1—N2	115.5 (3)	H7A—C7—H7B	109.5
C5—N1—H1N	126 (2)	C6—C7—H7C	109.5
N2—N1—H1N	115 (2)	H7A—C7—H7C	109.5
C6—N2—N1	119.0 (3)	H7B—C7—H7C	109.5
C2—C1—S1	112.4 (3)	C9—C8—C13	116.8 (3)
C2—C1—H1	123.8	C9—C8—C6	121.1 (3)
S1—C1—H1	123.8	C13—C8—C6	122.1 (3)
C1—C2—C3	112.9 (4)	C10—C9—C8	122.6 (4)
C1—C2—H2A	123.6	C10—C9—H9A	118.7
C3—C2—H2A	123.6	C8—C9—H9A	118.7
C4—C3—C2	112.0 (3)	C9—C10—C11	119.7 (4)
C4—C3—H3A	124.0	C9—C10—H10A	120.2
C2—C3—H3A	124.0	C11—C10—H10A	120.2
C3—C4—C5	130.5 (3)	C12—C11—C10	120.0 (4)
C3—C4—S1	111.3 (3)	C12—C11—H11A	120.0
C5—C4—S1	118.1 (3)	C10—C11—H11A	120.0
O1—C5—N1	122.7 (3)	C11—C12—C13	120.5 (4)
O1—C5—C4	121.9 (3)	C11—C12—H12A	119.8
N1—C5—C4	115.4 (3)	C13—C12—H12A	119.8
N2—C6—C8	115.4 (3)	O2—C13—C12	116.3 (3)
N2—C6—C7	123.7 (3)	O2—C13—C8	123.3 (3)
C8—C6—C7	120.9 (3)	C12—C13—C8	120.4 (3)
C5—N1—N2—C6	167.0 (3)	N2—C6—C8—C9	179.2 (3)
C4—S1—C1—C2	0.9 (3)	C7—C6—C8—C9	−0.7 (5)
S1—C1—C2—C3	−0.5 (4)	N2—C6—C8—C13	−2.3 (5)
C1—C2—C3—C4	−0.3 (5)	C7—C6—C8—C13	177.7 (3)
C2—C3—C4—C5	177.6 (3)	C13—C8—C9—C10	0.7 (5)
C2—C3—C4—S1	1.0 (4)	C6—C8—C9—C10	179.2 (3)
C1—S1—C4—C3	−1.1 (3)	C8—C9—C10—C11	−0.1 (6)
C1—S1—C4—C5	−178.1 (3)	C9—C10—C11—C12	−0.4 (6)
N2—N1—C5—O1	−8.5 (5)	C10—C11—C12—C13	0.3 (6)
N2—N1—C5—C4	172.4 (3)	C11—C12—C13—O2	−179.1 (3)
C3—C4—C5—O1	−153.3 (4)	C11—C12—C13—C8	0.4 (5)
S1—C4—C5—O1	23.1 (4)	C9—C8—C13—O2	178.5 (3)
C3—C4—C5—N1	25.8 (5)	C6—C8—C13—O2	0.1 (5)
S1—C4—C5—N1	−157.8 (3)	C9—C8—C13—C12	−0.8 (5)
N1—N2—C6—C8	175.2 (3)	C6—C8—C13—C12	−179.3 (3)
N1—N2—C6—C7	−4.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.94 (4)	2.11 (4)	3.023 (4)	164 (3)
O2—H2O···N2	0.81 (4)	1.80 (4)	2.536 (4)	150 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.94 (4)	2.11 (4)	3.023 (4)	164 (3)
O2—H2O⋯N2	0.81 (4)	1.80 (4)	2.536 (4)	150 (4)

Symmetry code: (i) .