(E)-N'-(2-Hy-droxy-benzyl-idene)furan-2-carbohydrazide.

In the title compound, C(12)H(10)N(2)O(3), the dihedral angle between the benzene ring and the furan ring is 16.12 (13)°. The conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond. Inter-molecular N-H⋯O hydrogen bonds with the keto group as acceptor lead to strands along [001]. The mol-ecule displays a trans configuration with respect to the C=N and N-N bonds.

Related literature

For historical background to aroylhydrazones, see: Offe et al. (1952 ▶); Craliz et al. (1955 ▶); Pickart et al. (1983 ▶); Arapov et al. (1987 ▶); Ranford et al. (1998 ▶); Savanini et al. (2002 ▶). For related structures, see: Monfared et al. (2010 ▶); Ali et al. (2005 ▶); Li et al. (2007 ▶); Diao et al. (2007 ▶).

Experimental

Crystal data

C12H10N2O3

M = 230.22

Orthorhombic,

a = 17.3539 (15) Å

b = 6.3320 (4) Å

c = 9.8613 (7) Å

V = 1083.61 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.46 × 0.29 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer

6705 measured reflections

1130 independent reflections

792 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.043

S = 0.81

1130 reflections

159 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.10 e Å−3

Δρmin = −0.11 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810024839/vm2028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024839/vm2028Isup2.hkl

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

C12H10N2O3	F(000) = 480
Mr = 230.22	Dx = 1.411 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6480 reflections
a = 17.3539 (15) Å	θ = 2.1–26.9°
b = 6.3320 (4) Å	µ = 0.10 mm−1
c = 9.8613 (7) Å	T = 293 K
V = 1083.61 (14) Å3	Prism, light yellow
Z = 4	0.46 × 0.29 × 0.20 mm

Stoe IPDS 2 diffractometer	792 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
graphite	θmax = 26.0°, θmin = 2.4°
Detector resolution: 6.67 pixels mm-1	h = −21→21
w scans	k = −6→7
6705 measured reflections	l = −11→12
1130 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.043	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ2(Fo2) + (0.0138P)2] where P = (Fo2 + 2Fc2)/3
1130 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.10 e Å−3
3 restraints	Δρmin = −0.11 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
C1	0.44074 (10)	0.4371 (3)	0.5468 (2)	0.0396 (5)
C2	0.43426 (12)	0.2756 (4)	0.6432 (2)	0.0459 (6)
C3	0.48301 (13)	0.1039 (4)	0.6372 (3)	0.0594 (7)
H3	0.4781	−0.0039	0.7006	0.071*
C4	0.53899 (13)	0.0898 (4)	0.5384 (3)	0.0616 (7)
H4	0.5710	−0.0278	0.5349	0.074*
C5	0.54754 (12)	0.2496 (4)	0.4452 (3)	0.0579 (7)
H5	0.5859	0.2417	0.3796	0.070*
C6	0.49918 (11)	0.4207 (4)	0.4496 (3)	0.0496 (6)
H6	0.5054	0.5285	0.3865	0.060*
C7	0.38950 (11)	0.6177 (4)	0.5438 (2)	0.0461 (6)
H7	0.3928	0.7123	0.4718	0.055*
C8	0.25245 (13)	0.9022 (4)	0.7261 (2)	0.0447 (5)
C9	0.21197 (12)	1.0979 (4)	0.6958 (2)	0.0449 (6)
C10	0.16454 (13)	1.2205 (4)	0.7684 (3)	0.0569 (6)
H10	0.1472	1.1948	0.8561	0.068*
C11	0.14591 (15)	1.3964 (4)	0.6865 (3)	0.0626 (8)
H11	0.1139	1.5085	0.7097	0.075*
C12	0.18302 (13)	1.3702 (4)	0.5694 (3)	0.0607 (7)
H12	0.1808	1.4634	0.4966	0.073*
N1	0.33997 (9)	0.6505 (3)	0.63712 (19)	0.0455 (5)
N2	0.29468 (9)	0.8264 (3)	0.62150 (19)	0.0489 (5)
H2	0.2931	0.8892	0.5442	0.059*
O1	0.38068 (10)	0.2824 (3)	0.74331 (17)	0.0594 (5)
O2	0.24940 (11)	0.8172 (2)	0.83793 (16)	0.0575 (4)
O3	0.22438 (8)	1.1887 (3)	0.57132 (16)	0.0557 (4)
H22	0.3504 (17)	0.397 (4)	0.736 (3)	0.095 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0403 (11)	0.0426 (14)	0.0360 (12)	−0.0038 (10)	−0.0032 (11)	−0.0029 (12)
C2	0.0445 (12)	0.0538 (16)	0.0395 (13)	−0.0066 (11)	−0.0031 (12)	−0.0030 (13)
C3	0.0668 (15)	0.0509 (16)	0.0604 (17)	0.0002 (14)	−0.0073 (15)	0.0084 (14)
C4	0.0566 (14)	0.0627 (18)	0.0653 (18)	0.0127 (13)	−0.0034 (15)	−0.0040 (18)
C5	0.0463 (14)	0.074 (2)	0.0536 (16)	0.0036 (13)	0.0022 (13)	−0.0168 (15)
C6	0.0493 (14)	0.0584 (16)	0.0412 (15)	−0.0033 (13)	0.0019 (11)	0.0001 (15)
C7	0.0469 (11)	0.0547 (16)	0.0366 (12)	−0.0040 (11)	0.0014 (12)	0.0014 (11)
C8	0.0444 (12)	0.0533 (14)	0.0364 (13)	0.0000 (12)	−0.0023 (10)	−0.0041 (14)
C9	0.0428 (12)	0.0559 (15)	0.0360 (13)	0.0037 (12)	−0.0005 (10)	−0.0039 (13)
C10	0.0599 (14)	0.0665 (18)	0.0444 (14)	0.0099 (15)	0.0048 (13)	−0.0046 (14)
C11	0.0652 (17)	0.0651 (18)	0.0576 (17)	0.0197 (14)	−0.0024 (13)	−0.0115 (16)
C12	0.0649 (15)	0.0568 (19)	0.0604 (17)	0.0135 (13)	−0.0125 (14)	0.0000 (15)
N1	0.0450 (10)	0.0506 (13)	0.0409 (10)	0.0042 (9)	0.0020 (10)	−0.0045 (10)
N2	0.0587 (10)	0.0532 (12)	0.0349 (11)	0.0110 (10)	0.0020 (10)	−0.0009 (10)
O1	0.0615 (10)	0.0708 (13)	0.0459 (10)	−0.0058 (10)	0.0095 (9)	0.0086 (10)
O2	0.0702 (10)	0.0643 (10)	0.0382 (10)	0.0069 (9)	0.0059 (9)	0.0018 (9)
O3	0.0592 (10)	0.0644 (11)	0.0434 (10)	0.0118 (8)	0.0015 (8)	0.0016 (10)

C1—C6	1.399 (3)	C8—O2	1.228 (3)
C1—C2	1.401 (3)	C8—N2	1.354 (3)
C1—C7	1.449 (3)	C8—C9	1.456 (3)
C2—O1	1.357 (3)	C9—C10	1.339 (3)
C2—C3	1.379 (3)	C9—O3	1.372 (3)
C3—C4	1.378 (3)	C10—C11	1.413 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.375 (4)	C11—C12	1.332 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.371 (3)	C12—O3	1.355 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	N1—N2	1.371 (2)
C7—N1	1.277 (3)	N2—H2	0.8600
C7—H7	0.9300	O1—H22	0.90 (3)
C6—C1—C2	117.9 (2)	O2—C8—N2	123.5 (2)
C6—C1—C7	119.3 (2)	O2—C8—C9	122.5 (2)
C2—C1—C7	122.75 (19)	N2—C8—C9	114.0 (2)
O1—C2—C3	118.5 (2)	C10—C9—O3	109.4 (2)
O1—C2—C1	121.7 (2)	C10—C9—C8	132.8 (2)
C3—C2—C1	119.8 (2)	O3—C9—C8	117.72 (19)
C4—C3—C2	120.9 (2)	C9—C10—C11	106.9 (2)
C4—C3—H3	119.5	C9—C10—H10	126.5
C2—C3—H3	119.5	C11—C10—H10	126.5
C5—C4—C3	120.0 (2)	C12—C11—C10	106.7 (2)
C5—C4—H4	120.0	C12—C11—H11	126.7
C3—C4—H4	120.0	C10—C11—H11	126.7
C6—C5—C4	119.6 (2)	C11—C12—O3	110.5 (2)
C6—C5—H5	120.2	C11—C12—H12	124.8
C4—C5—H5	120.2	O3—C12—H12	124.8
C5—C6—C1	121.6 (2)	C7—N1—N2	115.92 (19)
C5—C6—H6	119.2	C8—N2—N1	120.84 (19)
C1—C6—H6	119.2	C8—N2—H2	119.6
N1—C7—C1	121.8 (2)	N1—N2—H2	119.6
N1—C7—H7	119.1	C2—O1—H22	111.8 (19)
C1—C7—H7	119.1	C12—O3—C9	106.5 (2)
C6—C1—C2—O1	178.0 (2)	N2—C8—C9—C10	179.1 (2)
C7—C1—C2—O1	−2.3 (3)	O2—C8—C9—O3	174.7 (2)
C6—C1—C2—C3	−2.2 (3)	N2—C8—C9—O3	−3.9 (3)
C7—C1—C2—C3	177.5 (2)	O3—C9—C10—C11	0.1 (3)
O1—C2—C3—C4	−179.3 (2)	C8—C9—C10—C11	177.4 (2)
C1—C2—C3—C4	0.9 (3)	C9—C10—C11—C12	0.0 (3)
C2—C3—C4—C5	0.9 (4)	C10—C11—C12—O3	−0.1 (3)
C3—C4—C5—C6	−1.2 (4)	C1—C7—N1—N2	−179.55 (19)
C4—C5—C6—C1	−0.2 (3)	O2—C8—N2—N1	−2.7 (3)
C2—C1—C6—C5	1.9 (3)	C9—C8—N2—N1	175.82 (18)
C7—C1—C6—C5	−177.8 (2)	C7—N1—N2—C8	−165.59 (19)
C6—C1—C7—N1	−173.37 (19)	C11—C12—O3—C9	0.2 (3)
C2—C1—C7—N1	6.9 (3)	C10—C9—O3—C12	−0.2 (2)
O2—C8—C9—C10	−2.3 (4)	C8—C9—O3—C12	−177.90 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	2.21	2.900 (2)	137
O1—H22···N1	0.90 (3)	1.89 (3)	2.651 (3)	141 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.21	2.900 (2)	137
O1—H22⋯N1	0.90 (3)	1.89 (3)	2.651 (3)	141 (3)

Symmetry code: (i) .