N'-(4-Hy-droxy-benzyl-idene)thio-phene-2-carbohydrazide.

In the title compound, C(12)H(10)N(2)O(2)S, the dihedral angle between the benzene and thio-phene rings is 23.34 (16)°. In the crystal structure, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming (100) sheets.

Related literature

For background to the pharmacological properties of Schiff bases, see: Ren et al. (2002 ▶). For a related structure, see: Li et al. (2009 ▶).

Experimental

Crystal data

C12H10N2O2S

M = 246.28

Monoclinic,

a = 9.5622 (19) Å

b = 12.404 (3) Å

c = 9.991 (2) Å

β = 104.40 (3)°

V = 1147.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

10889 measured reflections

2629 independent reflections

1501 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.181

S = 1.07

2629 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.38 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/S1600536810021483/hb5483sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021483/hb5483Isup2.hkl

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

C12H10N2O2S	F(000) = 512
Mr = 246.28	Dx = 1.425 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1501 reflections
a = 9.5622 (19) Å	θ = 3.1–27.5°
b = 12.404 (3) Å	µ = 0.27 mm−1
c = 9.991 (2) Å	T = 293 K
β = 104.40 (3)°	Block, colorless
V = 1147.8 (4) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1501 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
graphite	θmax = 27.5°, θmin = 3.1°
phi and ω scans	h = −12→12
10889 measured reflections	k = −16→16
2629 independent reflections	l = −11→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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2629 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.37 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	0.89443 (10)	0.07271 (7)	0.19012 (8)	0.0713 (3)
N2	1.2232 (2)	0.37439 (19)	0.1118 (2)	0.0452 (6)
O1	1.1172 (2)	0.24125 (17)	0.27388 (17)	0.0548 (6)
N1	1.1217 (2)	0.29541 (19)	0.0602 (2)	0.0482 (6)
H1A	1.0911	0.2863	−0.0275	0.058*
C12	1.4377 (3)	0.5507 (2)	0.1730 (3)	0.0464 (6)
H12A	1.4518	0.4976	0.2407	0.056*
C4	0.9590 (3)	0.1566 (2)	0.0840 (2)	0.0435 (6)
C5	1.0717 (3)	0.2334 (2)	0.1475 (2)	0.0406 (6)
C7	1.3299 (3)	0.5378 (2)	0.0519 (2)	0.0430 (6)
C6	1.2339 (3)	0.4464 (2)	0.0230 (3)	0.0483 (7)
H6A	1.1759	0.4392	−0.0663	0.058*
C11	1.5235 (3)	0.6408 (2)	0.1941 (3)	0.0506 (7)
H11A	1.5936	0.6491	0.2767	0.061*
O2	1.5867 (3)	0.81085 (19)	0.1088 (2)	0.0816 (8)
H2C	1.6718	0.7957	0.1418	0.122*
C10	1.5063 (3)	0.7198 (2)	0.0930 (3)	0.0518 (7)
C8	1.3140 (3)	0.6189 (2)	−0.0471 (3)	0.0510 (7)
H8A	1.2427	0.6120	−0.1291	0.061*
C9	1.3999 (3)	0.7083 (2)	−0.0273 (3)	0.0569 (8)
H9A	1.3866	0.7613	−0.0951	0.068*
C3	0.8883 (4)	0.1398 (3)	−0.0502 (3)	0.0647 (9)
H3A	0.9077	0.1779	−0.1237	0.078*
C2	0.7834 (4)	0.0591 (3)	−0.0662 (3)	0.0756 (11)
H2B	0.7253	0.0377	−0.1512	0.091*
C1	0.7759 (4)	0.0163 (3)	0.0548 (3)	0.0765 (11)
H1B	0.7124	−0.0386	0.0632	0.092*

	U11	U22	U33	U12	U13	U23
S1	0.0791 (6)	0.0780 (6)	0.0592 (5)	−0.0243 (5)	0.0220 (4)	0.0166 (4)
N2	0.0506 (13)	0.0473 (14)	0.0398 (10)	−0.0127 (10)	0.0151 (10)	−0.0051 (9)
O1	0.0635 (13)	0.0682 (14)	0.0331 (9)	−0.0089 (10)	0.0129 (8)	0.0017 (8)
N1	0.0592 (15)	0.0545 (14)	0.0323 (10)	−0.0207 (11)	0.0138 (9)	−0.0059 (9)
C12	0.0476 (16)	0.0448 (15)	0.0466 (13)	−0.0047 (12)	0.0113 (12)	0.0066 (11)
C4	0.0461 (15)	0.0454 (15)	0.0416 (13)	−0.0069 (12)	0.0155 (11)	0.0010 (10)
C5	0.0446 (15)	0.0421 (14)	0.0374 (12)	−0.0003 (11)	0.0145 (10)	0.0003 (10)
C7	0.0485 (15)	0.0430 (15)	0.0398 (12)	−0.0050 (12)	0.0151 (11)	−0.0050 (10)
C6	0.0552 (17)	0.0510 (16)	0.0393 (13)	−0.0130 (13)	0.0129 (12)	−0.0049 (11)
C11	0.0465 (16)	0.0493 (17)	0.0514 (14)	−0.0048 (13)	0.0035 (12)	0.0062 (12)
O2	0.0694 (16)	0.0573 (15)	0.0975 (17)	−0.0248 (12)	−0.0184 (13)	0.0290 (12)
C10	0.0473 (16)	0.0409 (16)	0.0640 (17)	−0.0058 (13)	0.0078 (13)	0.0081 (12)
C8	0.0577 (18)	0.0497 (17)	0.0423 (13)	−0.0090 (14)	0.0064 (12)	0.0018 (11)
C9	0.063 (2)	0.0483 (18)	0.0543 (15)	−0.0072 (14)	0.0048 (14)	0.0120 (12)
C3	0.075 (2)	0.074 (2)	0.0457 (15)	−0.0327 (18)	0.0160 (15)	−0.0009 (14)
C2	0.079 (2)	0.085 (3)	0.0599 (18)	−0.041 (2)	0.0132 (17)	−0.0104 (16)
C1	0.073 (2)	0.071 (2)	0.088 (2)	−0.0361 (19)	0.0245 (19)	0.0017 (18)

S1—C1	1.685 (4)	C6—H6A	0.9300
S1—C4	1.707 (2)	C11—C10	1.387 (4)
N2—C6	1.281 (3)	C11—H11A	0.9300
N2—N1	1.385 (3)	O2—C10	1.354 (3)
O1—C5	1.233 (3)	O2—H2C	0.8200
N1—C5	1.337 (3)	C10—C9	1.375 (4)
N1—H1A	0.8600	C8—C9	1.364 (4)
C12—C11	1.371 (4)	C8—H8A	0.9300
C12—C7	1.390 (4)	C9—H9A	0.9300
C12—H12A	0.9300	C3—C2	1.398 (4)
C4—C3	1.360 (4)	C3—H3A	0.9300
C4—C5	1.461 (4)	C2—C1	1.339 (4)
C7—C8	1.392 (4)	C2—H2B	0.9300
C7—C6	1.443 (4)	C1—H1B	0.9300
C1—S1—C4	91.70 (14)	C12—C11—H11A	119.8
C6—N2—N1	113.9 (2)	C10—C11—H11A	119.8
C5—N1—N2	119.68 (19)	C10—O2—H2C	109.5
C5—N1—H1A	120.2	O2—C10—C9	117.6 (3)
N2—N1—H1A	120.2	O2—C10—C11	122.9 (3)
C11—C12—C7	120.9 (2)	C9—C10—C11	119.5 (3)
C11—C12—H12A	119.6	C9—C8—C7	121.9 (3)
C7—C12—H12A	119.6	C9—C8—H8A	119.1
C3—C4—C5	131.4 (2)	C7—C8—H8A	119.1
C3—C4—S1	110.6 (2)	C8—C9—C10	119.9 (3)
C5—C4—S1	118.01 (18)	C8—C9—H9A	120.0
O1—C5—N1	122.0 (2)	C10—C9—H9A	120.0
O1—C5—C4	122.1 (2)	C4—C3—C2	112.9 (3)
N1—C5—C4	115.9 (2)	C4—C3—H3A	123.5
C12—C7—C8	117.5 (3)	C2—C3—H3A	123.5
C12—C7—C6	124.2 (2)	C1—C2—C3	112.3 (3)
C8—C7—C6	118.3 (2)	C1—C2—H2B	123.9
N2—C6—C7	124.5 (2)	C3—C2—H2B	123.9
N2—C6—H6A	117.8	C2—C1—S1	112.6 (3)
C7—C6—H6A	117.8	C2—C1—H1B	123.7
C12—C11—C10	120.3 (3)	S1—C1—H1B	123.7

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.09	2.887 (3)	154
O2—H2C···O1ii	0.82	2.10	2.913 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.09	2.887 (3)	154
O2—H2C⋯O1ii	0.82	2.10	2.913 (3)	174

Symmetry codes: (i) ; (ii) .