N'-(Furan-2-ylmethyl-ene)-2-hydroxy-benzohydrazide.

In the title mol-ecule, C(12)H(10)N(2)O(3), the aromatic and furan rings form a dihedral angle of 8.89 (1)° and an intra-molecular N-H⋯O hydrogen bond occurs. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running along the c axis.

Related literature

For background on Schiff bases, see: Garnovskii et al. (1993 ▶); Anderson et al. (1997 ▶); Musie et al., (2001 ▶); Paul et al. (2002 ▶); Yang, (2006 ▶). For reference bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H10N2O3

M = 230.22

Monoclinic,

a = 4.9898 (5) Å

b = 20.662 (2) Å

c = 10.6994 (11) Å

β = 101.421 (2)°

V = 1081.24 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.98, T max = 0.99

5631 measured reflections

1904 independent reflections

1451 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.02

1904 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034636/bg2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034636/bg2220Isup2.hkl

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

C12H10N2O3	F(000) = 480
Mr = 230.22	Dx = 1.414 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1748 reflections
a = 4.9898 (5) Å	θ = 2.2–25.0°
b = 20.662 (2) Å	µ = 0.10 mm−1
c = 10.6994 (11) Å	T = 295 K
β = 101.421 (2)°	Block, orange
V = 1081.24 (19) Å3	0.12 × 0.10 × 0.06 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	1904 independent reflections
Radiation source: fine-focus sealed tube	1451 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
Tmin = 0.98, Tmax = 0.99	k = −24→21
5631 measured reflections	l = −11→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.1418P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1904 reflections	Δρmax = 0.12 e Å−3
156 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0107 (19)

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
O1	0.2921 (2)	0.22463 (6)	0.59528 (10)	0.0611 (4)
H1	0.3615	0.2261	0.5320	0.092*
O2	0.2021 (2)	0.22907 (5)	0.97330 (9)	0.0541 (3)
O3	−0.6276 (3)	0.42331 (7)	0.68440 (12)	0.0815 (4)
N1	0.0370 (2)	0.26559 (6)	0.77544 (11)	0.0435 (3)
H1A	0.0365	0.2638	0.6951	0.052*
N2	−0.1342 (2)	0.30720 (6)	0.82213 (11)	0.0422 (3)
C1	0.4351 (3)	0.18305 (7)	0.68139 (14)	0.0415 (4)
C2	0.3961 (3)	0.18397 (7)	0.80733 (13)	0.0385 (3)
C3	0.5525 (3)	0.14165 (7)	0.89334 (15)	0.0493 (4)
H3	0.5312	0.1417	0.9778	0.059*
C4	0.7373 (3)	0.09972 (8)	0.85745 (16)	0.0560 (4)
H4	0.8409	0.0723	0.9171	0.067*
C5	0.7674 (3)	0.09876 (8)	0.73201 (16)	0.0549 (4)
H5	0.8892	0.0699	0.7065	0.066*
C6	0.6191 (3)	0.14000 (8)	0.64527 (15)	0.0508 (4)
H6	0.6417	0.1392	0.5611	0.061*
C7	0.2058 (3)	0.22765 (7)	0.85884 (13)	0.0397 (4)
C8	−0.2876 (3)	0.34231 (7)	0.74000 (15)	0.0483 (4)
H8	−0.2834	0.3378	0.6539	0.058*
C9	−0.4676 (3)	0.38898 (7)	0.77975 (14)	0.0460 (4)
C10	−0.5197 (3)	0.40836 (8)	0.89143 (17)	0.0582 (5)
H10	−0.4375	0.3928	0.9714	0.070*
C11	−0.7221 (4)	0.45682 (9)	0.8659 (2)	0.0668 (5)
H11	−0.7991	0.4793	0.9254	0.080*
C12	−0.7803 (4)	0.46390 (9)	0.7418 (2)	0.0767 (6)
H12	−0.9090	0.4928	0.6988	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0660 (8)	0.0871 (9)	0.0369 (6)	0.0281 (6)	0.0263 (5)	0.0161 (6)
O2	0.0647 (7)	0.0696 (8)	0.0325 (6)	0.0026 (6)	0.0206 (5)	0.0006 (5)
O3	0.0984 (10)	0.0848 (9)	0.0550 (8)	0.0339 (8)	0.0000 (7)	−0.0057 (7)
N1	0.0502 (7)	0.0512 (7)	0.0328 (7)	0.0022 (6)	0.0171 (6)	−0.0049 (6)
N2	0.0457 (7)	0.0457 (7)	0.0386 (7)	−0.0034 (6)	0.0167 (6)	−0.0075 (6)
C1	0.0397 (8)	0.0502 (9)	0.0365 (8)	−0.0013 (7)	0.0120 (6)	0.0019 (7)
C2	0.0386 (8)	0.0434 (8)	0.0350 (7)	−0.0083 (6)	0.0107 (6)	−0.0015 (6)
C3	0.0566 (9)	0.0529 (9)	0.0388 (8)	−0.0027 (8)	0.0103 (7)	0.0013 (7)
C4	0.0582 (10)	0.0533 (10)	0.0538 (10)	0.0060 (8)	0.0046 (8)	0.0067 (8)
C5	0.0525 (10)	0.0530 (10)	0.0612 (11)	0.0058 (8)	0.0162 (8)	−0.0053 (8)
C6	0.0512 (9)	0.0611 (10)	0.0439 (9)	0.0048 (8)	0.0185 (7)	−0.0016 (8)
C7	0.0427 (8)	0.0450 (8)	0.0343 (8)	−0.0099 (7)	0.0146 (6)	−0.0019 (7)
C8	0.0584 (10)	0.0526 (9)	0.0362 (8)	−0.0008 (8)	0.0147 (8)	−0.0076 (7)
C9	0.0475 (9)	0.0461 (9)	0.0439 (9)	−0.0030 (7)	0.0080 (7)	−0.0032 (7)
C10	0.0629 (11)	0.0656 (11)	0.0506 (10)	0.0079 (9)	0.0220 (8)	−0.0004 (8)
C11	0.0634 (12)	0.0592 (11)	0.0856 (15)	0.0003 (9)	0.0337 (11)	−0.0125 (10)
C12	0.0694 (13)	0.0596 (12)	0.0966 (17)	0.0202 (10)	0.0055 (12)	−0.0088 (11)

O1—C1	1.3549 (17)	C3—H3	0.9300
O1—H1	0.8200	C4—C5	1.380 (2)
O2—C7	1.2288 (16)	C4—H4	0.9300
O3—C12	1.359 (2)	C5—C6	1.365 (2)
O3—C9	1.3633 (19)	C5—H5	0.9300
N1—C7	1.3503 (18)	C6—H6	0.9300
N1—N2	1.3737 (16)	C8—C9	1.438 (2)
N1—H1A	0.8600	C8—H8	0.9300
N2—C8	1.2720 (19)	C9—C10	1.334 (2)
C1—C6	1.387 (2)	C10—C11	1.410 (2)
C1—C2	1.3991 (19)	C10—H10	0.9300
C2—C3	1.391 (2)	C11—C12	1.310 (3)
C2—C7	1.492 (2)	C11—H11	0.9300
C3—C4	1.374 (2)	C12—H12	0.9300
C1—O1—H1	109.5	C5—C6—C1	120.69 (15)
C12—O3—C9	106.28 (15)	C5—C6—H6	119.7
C7—N1—N2	118.33 (11)	C1—C6—H6	119.7
C7—N1—H1A	120.8	O2—C7—N1	120.95 (13)
N2—N1—H1A	120.8	O2—C7—C2	121.25 (13)
C8—N2—N1	115.98 (12)	N1—C7—C2	117.81 (12)
O1—C1—C6	120.38 (13)	N2—C8—C9	120.25 (13)
O1—C1—C2	119.43 (13)	N2—C8—H8	119.9
C6—C1—C2	120.19 (14)	C9—C8—H8	119.9
C3—C2—C1	117.51 (14)	C10—C9—O3	108.97 (14)
C3—C2—C7	116.76 (12)	C10—C9—C8	135.24 (16)
C1—C2—C7	125.71 (13)	O3—C9—C8	115.78 (14)
C4—C3—C2	122.05 (14)	C9—C10—C11	107.40 (17)
C4—C3—H3	119.0	C9—C10—H10	126.3
C2—C3—H3	119.0	C11—C10—H10	126.3
C3—C4—C5	119.29 (15)	C12—C11—C10	106.37 (17)
C3—C4—H4	120.4	C12—C11—H11	126.8
C5—C4—H4	120.4	C10—C11—H11	126.8
C6—C5—C4	120.24 (15)	C11—C12—O3	110.96 (17)
C6—C5—H5	119.9	C11—C12—H12	124.5
C4—C5—H5	119.9	O3—C12—H12	124.5
C7—N1—N2—C8	179.41 (13)	C3—C2—C7—O2	4.9 (2)
O1—C1—C2—C3	−178.33 (13)	C1—C2—C7—O2	−173.54 (14)
C6—C1—C2—C3	1.5 (2)	C3—C2—C7—N1	−175.00 (13)
O1—C1—C2—C7	0.1 (2)	C1—C2—C7—N1	6.6 (2)
C6—C1—C2—C7	179.90 (13)	N1—N2—C8—C9	−177.93 (12)
C1—C2—C3—C4	−0.6 (2)	C12—O3—C9—C10	−0.45 (19)
C7—C2—C3—C4	−179.16 (13)	C12—O3—C9—C8	179.81 (14)
C2—C3—C4—C5	−0.8 (2)	N2—C8—C9—C10	1.6 (3)
C3—C4—C5—C6	1.4 (3)	N2—C8—C9—O3	−178.74 (14)
C4—C5—C6—C1	−0.5 (2)	O3—C9—C10—C11	0.28 (19)
O1—C1—C6—C5	178.84 (14)	C8—C9—C10—C11	179.95 (17)
C2—C1—C6—C5	−1.0 (2)	C9—C10—C11—C12	0.0 (2)
N2—N1—C7—O2	1.8 (2)	C10—C11—C12—O3	−0.3 (2)
N2—N1—C7—C2	−178.36 (11)	C9—O3—C12—C11	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	2.14	2.804 (2)	139
N1—H1A···O1	0.86	1.99	2.650 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	2.14	2.804 (2)	139
N1—H1A⋯O1	0.86	1.99	2.650 (2)	133

Symmetry code: (i) .