(E)-N'-(2-Furylmethyl-ene)benzo-hydrazide.

In the title compound, C(12)H(10)N(2)O(2), the dihedral angle between the benzene and furan rings is 52.54 (7)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions link the mol-ecules.

Related literature

For biological properties of Schiff base ligands, see: Chakraborty et al. (1996 ▶); Jeewoth et al. (1999 ▶). For related crystal structures, see: Fun et al. (2008 ▶); Cui et al. (2009 ▶); Nie (2008 ▶).

Experimental

Crystal data

C12H10N2O2

M = 214.22

Monoclinic,

a = 12.3955 (11) Å

b = 9.4777 (9) Å

c = 9.6845 (10) Å

β = 110.610 (1)°

V = 1064.93 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.43 × 0.38 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.973

5190 measured reflections

1882 independent reflections

1360 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.05

1882 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 I, global. DOI: 10.1107/S1600536809042251/bq2168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042251/bq2168Isup2.hkl

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

C12H10N2O2	F(000) = 448
Mr = 214.22	Dx = 1.336 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1760 reflections
a = 12.3955 (11) Å	θ = 2.8–25.6°
b = 9.4777 (9) Å	µ = 0.09 mm−1
c = 9.6845 (10) Å	T = 298 K
β = 110.610 (1)°	Needle, green
V = 1064.93 (18) Å3	0.43 × 0.38 × 0.30 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1882 independent reflections
Radiation source: fine-focus sealed tube	1360 reflections with I > 2σ(I)
graphite	Rint = 0.032
phi and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.961, Tmax = 0.973	k = −11→5
5190 measured reflections	l = −11→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.2066P] where P = (Fo2 + 2Fc2)/3
1882 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 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
N1	0.23549 (11)	0.22758 (14)	0.10288 (15)	0.0393 (4)
H1	0.2462	0.2263	0.1956	0.047*
N2	0.18065 (12)	0.11622 (15)	0.01303 (15)	0.0394 (4)
O1	0.26227 (11)	0.34211 (13)	−0.08757 (13)	0.0525 (4)
O2	0.05357 (11)	−0.11197 (14)	−0.14345 (14)	0.0552 (4)
C1	0.27183 (14)	0.33810 (18)	0.04323 (18)	0.0369 (4)
C2	0.32908 (13)	0.45449 (17)	0.14650 (18)	0.0357 (4)
C3	0.31657 (15)	0.47508 (18)	0.28218 (19)	0.0439 (4)
H3	0.2698	0.4148	0.3122	0.053*
C4	0.37320 (17)	0.5846 (2)	0.3724 (2)	0.0539 (5)
H4	0.3642	0.5982	0.4628	0.065*
C5	0.44318 (17)	0.6740 (2)	0.3290 (2)	0.0576 (6)
H5	0.4822	0.7468	0.3908	0.069*
C6	0.45522 (16)	0.6555 (2)	0.1942 (2)	0.0553 (5)
H6	0.5019	0.7161	0.1646	0.066*
C7	0.39802 (15)	0.5469 (2)	0.1033 (2)	0.0460 (5)
H7	0.4057	0.5354	0.0118	0.055*
C8	0.17622 (14)	0.00187 (18)	0.07975 (19)	0.0407 (4)
H8	0.2088	−0.0011	0.1821	0.049*
C9	0.12239 (14)	−0.12242 (18)	0.00150 (19)	0.0406 (4)
C10	0.12911 (17)	−0.2579 (2)	0.0460 (2)	0.0574 (5)
H10	0.1701	−0.2924	0.1398	0.069*
C11	0.06160 (19)	−0.3374 (2)	−0.0779 (3)	0.0693 (6)
H11	0.0504	−0.4346	−0.0818	0.083*
C12	0.01745 (18)	−0.2464 (3)	−0.1875 (3)	0.0635 (6)
H12	−0.0316	−0.2708	−0.2817	0.076*

	U11	U22	U33	U12	U13	U23
N1	0.0512 (9)	0.0397 (8)	0.0276 (7)	−0.0026 (7)	0.0147 (6)	−0.0027 (6)
N2	0.0459 (8)	0.0386 (8)	0.0341 (8)	−0.0018 (7)	0.0146 (6)	−0.0038 (7)
O1	0.0821 (9)	0.0482 (8)	0.0309 (7)	−0.0056 (7)	0.0245 (6)	−0.0012 (6)
O2	0.0565 (8)	0.0579 (9)	0.0459 (8)	−0.0045 (7)	0.0116 (6)	−0.0062 (7)
C1	0.0414 (9)	0.0386 (10)	0.0318 (9)	0.0061 (8)	0.0142 (7)	0.0030 (8)
C2	0.0383 (9)	0.0362 (9)	0.0332 (9)	0.0047 (7)	0.0134 (7)	0.0017 (8)
C3	0.0554 (11)	0.0432 (10)	0.0381 (10)	−0.0067 (9)	0.0225 (8)	−0.0012 (8)
C4	0.0699 (13)	0.0579 (13)	0.0391 (11)	−0.0131 (10)	0.0257 (10)	−0.0102 (9)
C5	0.0634 (12)	0.0576 (13)	0.0502 (12)	−0.0191 (11)	0.0180 (10)	−0.0126 (10)
C6	0.0571 (12)	0.0598 (13)	0.0522 (12)	−0.0185 (10)	0.0233 (10)	−0.0014 (10)
C7	0.0509 (11)	0.0534 (11)	0.0386 (10)	−0.0041 (9)	0.0218 (9)	0.0008 (9)
C8	0.0451 (10)	0.0430 (10)	0.0338 (9)	0.0013 (8)	0.0136 (8)	−0.0006 (8)
C9	0.0428 (10)	0.0429 (11)	0.0378 (10)	0.0015 (8)	0.0162 (8)	−0.0012 (8)
C10	0.0647 (13)	0.0460 (12)	0.0627 (13)	0.0011 (10)	0.0241 (11)	0.0039 (11)
C11	0.0781 (15)	0.0457 (12)	0.0926 (19)	−0.0118 (12)	0.0406 (14)	−0.0163 (13)
C12	0.0560 (12)	0.0711 (15)	0.0633 (14)	−0.0171 (12)	0.0210 (11)	−0.0292 (13)

N1—C1	1.348 (2)	C5—C6	1.376 (3)
N1—N2	1.3844 (19)	C5—H5	0.9300
N1—H1	0.8600	C6—C7	1.377 (3)
N2—C8	1.273 (2)	C6—H6	0.9300
O1—C1	1.2306 (19)	C7—H7	0.9300
O2—C9	1.366 (2)	C8—C9	1.432 (2)
O2—C12	1.368 (2)	C8—H8	0.9300
C1—C2	1.490 (2)	C9—C10	1.348 (3)
C2—C7	1.387 (2)	C10—C11	1.415 (3)
C2—C3	1.390 (2)	C10—H10	0.9300
C3—C4	1.379 (2)	C11—C12	1.327 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.380 (3)	C12—H12	0.9300
C4—H4	0.9300
C1—N1—N2	119.16 (13)	C5—C6—H6	120.1
C1—N1—H1	120.4	C7—C6—H6	120.1
N2—N1—H1	120.4	C6—C7—C2	120.79 (17)
C8—N2—N1	115.43 (14)	C6—C7—H7	119.6
C9—O2—C12	105.68 (16)	C2—C7—H7	119.6
O1—C1—N1	122.65 (16)	N2—C8—C9	121.81 (16)
O1—C1—C2	121.24 (15)	N2—C8—H8	119.1
N1—C1—C2	116.08 (14)	C9—C8—H8	119.1
C7—C2—C3	118.82 (16)	C10—C9—O2	110.11 (16)
C7—C2—C1	117.59 (15)	C10—C9—C8	130.51 (17)
C3—C2—C1	123.59 (15)	O2—C9—C8	119.36 (15)
C4—C3—C2	120.22 (17)	C9—C10—C11	106.54 (19)
C4—C3—H3	119.9	C9—C10—H10	126.7
C2—C3—H3	119.9	C11—C10—H10	126.7
C3—C4—C5	120.23 (18)	C12—C11—C10	106.65 (19)
C3—C4—H4	119.9	C12—C11—H11	126.7
C5—C4—H4	119.9	C10—C11—H11	126.7
C6—C5—C4	120.03 (18)	C11—C12—O2	111.01 (18)
C6—C5—H5	120.0	C11—C12—H12	124.5
C4—C5—H5	120.0	O2—C12—H12	124.5
C5—C6—C7	119.89 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.14	2.972 (2)	163
C10—H10···Cg1ii	0.93	2.85	3.498 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.14	2.972 (2)	163
C10—H10⋯Cg1ii	0.93	2.84	3.498 (2)	128

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C2–C7 ring.