N'-Benzyl-idene-furan-2-carbohydrazide.

In the title compound, C(12)H(10)N(2)O(2), the dihedral angle between the benzene ring and the furan ring is 24.6 (2)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(4) chains propagating in [010].

Related literature

For background to Schiff bases as ligands, see: Polt et al. (2003 ▶). For a related structure, see: Jiang (2010 ▶).

Experimental

Crystal data

C12H10N2O2

M = 214.22

Orthorhombic,

a = 11.628 (2) Å

b = 7.6638 (15) Å

c = 23.873 (5) Å

V = 2127.4 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

15748 measured reflections

1915 independent reflections

841 reflections with I > 2σ(I)

R int = 0.180

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.182

S = 0.87

1915 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.35 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/S1600536810021471/hb5485sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021471/hb5485Isup2.hkl

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

C12H10N2O2	F(000) = 896
Mr = 214.22	Dx = 1.338 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2542 reflections
a = 11.628 (2) Å	θ = 2.7–25.4°
b = 7.6638 (15) Å	µ = 0.09 mm−1
c = 23.873 (5) Å	T = 293 K
V = 2127.4 (7) Å3	Block, colorless
Z = 8	0.22 × 0.20 × 0.18 mm

Bruker SMART CCD diffractometer	841 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.180
graphite	θmax = 25.3°, θmin = 3.3°
phi and ω scans	h = −13→13
15748 measured reflections	k = −9→9
1915 independent reflections	l = −28→28

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)] = 0.069	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.0916P)2] where P = (Fo2 + 2Fc2)/3
S = 0.87	(Δ/σ)max < 0.001
1915 reflections	Δρmax = 0.48 e Å−3
146 parameters	Δρmin = −0.35 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (4)

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
C7	0.6392 (3)	0.2814 (4)	0.22579 (15)	0.0427 (9)
N2	0.7400 (2)	0.2911 (4)	0.13973 (12)	0.0444 (8)
O2	0.89248 (19)	0.4222 (3)	0.06644 (10)	0.0525 (7)
C6	0.6608 (3)	0.2226 (4)	0.16890 (15)	0.0464 (9)
H6A	0.6161	0.1338	0.1537	0.056*
N1	0.7595 (2)	0.2165 (4)	0.08817 (12)	0.0468 (8)
H1A	0.7204	0.1273	0.0774	0.056*
C11	0.5250 (3)	0.2748 (5)	0.30936 (18)	0.0614 (11)
H11A	0.4599	0.2357	0.3282	0.074*
C5	0.8408 (3)	0.2861 (4)	0.05515 (15)	0.0433 (9)
O1	0.8127 (2)	0.0388 (3)	−0.00680 (11)	0.0624 (8)
C12	0.5431 (3)	0.2243 (5)	0.25478 (17)	0.0565 (11)
H12A	0.4905	0.1511	0.2372	0.068*
C2	0.9298 (4)	0.0939 (6)	−0.07761 (19)	0.0717 (13)
H2B	0.9697	0.0836	−0.1112	0.086*
C8	0.7157 (3)	0.3882 (5)	0.25381 (16)	0.0499 (10)
H8A	0.7816	0.4262	0.2354	0.060*
C4	0.8663 (3)	0.1949 (4)	0.00321 (15)	0.0457 (9)
C3	0.9374 (3)	0.2318 (5)	−0.03877 (18)	0.0619 (12)
H4A	0.9835	0.3304	−0.0419	0.074*
C10	0.6010 (4)	0.3816 (5)	0.33627 (18)	0.0617 (11)
H10A	0.5884	0.4148	0.3732	0.074*
C9	0.6968 (3)	0.4393 (5)	0.30781 (17)	0.0607 (11)
H9A	0.7488	0.5134	0.3254	0.073*
C1	0.8544 (4)	−0.0182 (6)	−0.05660 (18)	0.0746 (13)
H1B	0.8329	−0.1222	−0.0737	0.090*

	U11	U22	U33	U12	U13	U23
C7	0.047 (2)	0.0397 (19)	0.042 (2)	0.0015 (16)	0.0025 (17)	0.0011 (17)
N2	0.0508 (17)	0.0434 (17)	0.0389 (19)	−0.0018 (14)	0.0016 (14)	−0.0050 (14)
O2	0.0574 (14)	0.0490 (15)	0.0512 (18)	−0.0076 (12)	0.0024 (13)	−0.0054 (12)
C6	0.052 (2)	0.0403 (19)	0.047 (2)	−0.0016 (17)	−0.0001 (19)	−0.0025 (17)
N1	0.0558 (18)	0.0463 (17)	0.0384 (19)	−0.0070 (14)	0.0023 (15)	−0.0081 (14)
C11	0.058 (2)	0.073 (3)	0.054 (3)	0.005 (2)	0.019 (2)	0.001 (2)
C5	0.0469 (19)	0.0411 (19)	0.042 (2)	0.0030 (17)	−0.0022 (18)	0.0021 (18)
O1	0.0769 (18)	0.0604 (17)	0.0499 (19)	−0.0157 (13)	0.0153 (14)	−0.0151 (13)
C12	0.051 (2)	0.060 (2)	0.059 (3)	−0.0034 (19)	0.007 (2)	−0.006 (2)
C2	0.085 (3)	0.080 (3)	0.051 (3)	−0.011 (2)	0.024 (2)	−0.006 (2)
C8	0.051 (2)	0.051 (2)	0.047 (3)	−0.0037 (18)	0.0013 (19)	−0.0039 (18)
C4	0.051 (2)	0.0434 (19)	0.043 (3)	−0.0017 (16)	−0.0007 (18)	−0.0012 (18)
C3	0.070 (3)	0.062 (3)	0.053 (3)	−0.010 (2)	0.012 (2)	−0.005 (2)
C10	0.080 (3)	0.068 (3)	0.038 (2)	0.016 (2)	0.007 (2)	−0.001 (2)
C9	0.073 (3)	0.062 (3)	0.048 (3)	0.002 (2)	−0.003 (2)	−0.010 (2)
C1	0.101 (3)	0.069 (3)	0.053 (3)	−0.007 (3)	0.019 (2)	−0.021 (2)

C7—C8	1.382 (5)	O1—C4	1.370 (4)
C7—C12	1.385 (5)	C12—H12A	0.9300
C7—C6	1.453 (5)	C2—C1	1.327 (6)
N2—C6	1.268 (4)	C2—C3	1.408 (5)
N2—N1	1.376 (4)	C2—H2B	0.9300
O2—C5	1.234 (4)	C8—C9	1.365 (5)
C6—H6A	0.9300	C8—H8A	0.9300
N1—C5	1.342 (4)	C4—C3	1.329 (5)
N1—H1A	0.8600	C3—H4A	0.9300
C11—C10	1.366 (5)	C10—C9	1.377 (5)
C11—C12	1.376 (5)	C10—H10A	0.9300
C11—H11A	0.9300	C9—H9A	0.9300
C5—C4	1.454 (5)	C1—H1B	0.9300
O1—C1	1.357 (4)
C8—C7—C12	117.7 (4)	C1—C2—H2B	126.9
C8—C7—C6	121.6 (3)	C3—C2—H2B	126.9
C12—C7—C6	120.6 (3)	C9—C8—C7	121.6 (4)
C6—N2—N1	116.0 (3)	C9—C8—H8A	119.2
N2—C6—C7	120.7 (3)	C7—C8—H8A	119.2
N2—C6—H6A	119.6	C3—C4—O1	109.7 (3)
C7—C6—H6A	119.6	C3—C4—C5	131.9 (3)
C5—N1—N2	118.4 (3)	O1—C4—C5	118.4 (3)
C5—N1—H1A	120.8	C4—C3—C2	107.4 (3)
N2—N1—H1A	120.8	C4—C3—H4A	126.3
C10—C11—C12	121.0 (4)	C2—C3—H4A	126.3
C10—C11—H11A	119.5	C11—C10—C9	119.0 (4)
C12—C11—H11A	119.5	C11—C10—H10A	120.5
O2—C5—N1	123.5 (3)	C9—C10—H10A	120.5
O2—C5—C4	119.5 (3)	C8—C9—C10	120.2 (4)
N1—C5—C4	117.0 (3)	C8—C9—H9A	119.9
C1—O1—C4	105.8 (3)	C10—C9—H9A	119.9
C11—C12—C7	120.6 (4)	C2—C1—O1	111.0 (4)
C11—C12—H12A	119.7	C2—C1—H1B	124.5
C7—C12—H12A	119.7	O1—C1—H1B	124.5
C1—C2—C3	106.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.06	2.911 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.06	2.911 (4)	168

Symmetry code: (i) .