N′-Benzyl­idene­furan-2-carbohydrazide

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536810021471

organic compounds

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Volume 66| Part 7| July 2010| Page o1720

doi:10.1107/S1600536810021471

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N′-Benzylidenefuran-2-carbohydrazide

Yu-Feng Li ^a and Fang-Fang Jian ^b ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 4 June 2010; accepted 5 June 2010; online 18 June 2010)

In the title compound, C₁₂H₁₀N₂O₂, the dihedral angle between the benzene ring and the furan ring is 24.6 (2)°. In the crystal, molecules 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_r = 214.22
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.069
wR(F²) = 0.182
S = 0.87
1915 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021471/hb5485sup1.cif

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

checkCIF report

Comment top

Metal complexes based on Schiff bases have attracted much attention because they can be utilized as effective ligands to form the compounds with optically active (Polt et al., 2003). As part of our search for new Schiff base compounds we synthesized the title compound (I), and describe its structure here. The dihedral angle between the benzene ring and the furan ring is 24.6 (2)°. In the crystal lattice, the N—H···O hydrogen bonds which form chains stable the molecule structures.

Bond lengths and angles are comparable to those in a related material (Jiang, 2010).

Related literature top

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

Experimental top

A mixture of benzaldehyde (0.1 mol), and furan-2-carbohydrazide (0.1 mol) was stirred in refluxing ethanol (20 ml) for 2 h to afford the title compound (0.096 mol, yield 96%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.

N'-Benzylidenefuran-2-carbohydrazide top

Crystal data top

C₁₂H₁₀N₂O₂	F(000) = 896
M_r = 214.22	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0916P)²] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max < 0.001
1915 reflections	Δρ_max = 0.48 e Å⁻³
146 parameters	Δρ_min = −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)

Crystal data top

C₁₂H₁₀N₂O₂	V = 2127.4 (7) Å³
M_r = 214.22	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.628 (2) Å	µ = 0.09 mm⁻¹
b = 7.6638 (15) Å	T = 293 K
c = 23.873 (5) Å	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	841 reflections with I > 2σ(I)
15748 measured reflections	R_int = 0.180
1915 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 0.87	Δρ_max = 0.48 e Å⁻³
1915 reflections	Δρ_min = −0.35 e Å⁻³
146 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂O₂
M_r	214.22
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	11.628 (2), 7.6638 (15), 23.873 (5)
V (Å³)	2127.4 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15748, 1915, 841
R_int	0.180
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.182, 0.87
No. of reflections	1915
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.35

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jiang, J.-H. (2010). Acta Cryst. E66, o627. Web of Science CSD CrossRef IUCr Journals Google Scholar
Polt, R., Kelly, B. D. & Dangel, B. D. (2003). Inorg. Chem. 42, 566–574. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1720

doi:10.1107/S1600536810021471

Open

access