1-(2-Furylmethyl­ene)-2-(2-nitro­phen­yl)hydrazine

Yin, Z.-G.; Fei, Z.-L.; Qian, H.-Y.; Zhu, X.-W.; Zhang, C.-X.

doi:10.1107/S1600536809037052

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2534

doi:10.1107/S1600536809037052

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1-(2-Furylmethylene)-2-(2-nitrophenyl)hydrazine

Zhi-Gang Yin,^a ^* Zong-Lei Fei,^a Heng-Yu Qian,^a Xue-Wen Zhu ^a and Chun-Xia Zhang ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Materials & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: yinck@263.net

(Received 11 September 2009; accepted 13 September 2009; online 26 September 2009)

The title Schiff base compound, C₁₁H₉N₃O₃, was obtained from a condensation reaction of furan-2-carbaldehyde and 2-nitrophenylhydrazine. The molecule is roughly planar, the largest deviation from the mean plane defined by all non-H atoms being 0.097 (4). An in ntramolecular N—H⋯O hydrogen bond might influence the planar conformation of the molecule. In the crystal, weak C—H⋯O hydrogen bonds link the molecules, forming a chain.

Related literature

For the role played by Schiff base compounds in the development of various proteins and enzymes, see: Kahwa et al. (1986 ); Santos et al. (2001 ).

Experimental

Crystal data

C₁₁H₉N₃O₃
M_r = 231.21
Monoclinic, P 2₁ /n
a = 15.852 (3) Å
b = 3.8000 (12) Å
c = 17.721 (4) Å
β = 97.89 (2)°
V = 1057.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.979, T_max = 0.982
3497 measured reflections
2033 independent reflections
619 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.195
S = 0.73
2033 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.98	2.599 (5)	128
C2—H2A⋯O2ⁱ	0.93	2.48	3.360 (7)	158
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037052/dn2486sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037052/dn2486Isup2.hkl

checkCIF report

Comment top

The chemistry of Schiff base has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our interest in the study of the coordination chemistry of Schiff bases, we synthesized the title compound and determined its crystal structure.

The whole molecule is roughly planar with the largest deviations from the mean plane being -0.0973 (0.0041) at O3 (Fig. 1). The phenyl and the furan rings are slightly twisted from each other making a dihedral angle of 4.8 (3)°.

The intramolecular N—H···O hydrogen bond might influence the planar conformation of the molecule. Weak intermolecular C-H···O hydrogen bonds link the molecule forming a chain parallel to the (1 0 1) plane (Table 1, Fig. 2).

Related literature top

For the role played by Schiff base compounds in the development of various proteins and enzymes, see: Kahwa et al. (1986); Santos et al. (2001).

Experimental top

2-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (15 ml), The mixture was stirred for several minitutes at 351k, furan-2-carbaldehyde (1 mmol, 0.096 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol, red single crystals of (I) was obtained after 3 d.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997); PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of (I) with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen are represented as small sphere of arbitrary radii. Intramolecular N-H···O hydrogen bond is shown as dashed lines.
	Fig. 2. Partial packing view showing the chain formed by C-H···O hydrogen bonds.H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) x+1/2, -y+1/2, z-1/2]

1-(2-Furylmethylene)-2-(2-nitrophenyl)hydrazine top

Crystal data top

C₁₁H₉N₃O₃	F(000) = 480
M_r = 231.21	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1960 reflections
a = 15.852 (3) Å	θ = 3.2–28.2°
b = 3.8000 (12) Å	µ = 0.11 mm⁻¹
c = 17.721 (4) Å	T = 296 K
β = 97.89 (2)°	Block, red
V = 1057.4 (5) Å³	0.21 × 0.19 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2033 independent reflections
Radiation source: fine-focus sealed tube	619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 26.0°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→19
T_min = 0.979, T_max = 0.982	k = −4→4
3497 measured reflections	l = −21→21

Refinement top

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 0.73	w = 1/[σ²(F_o²) + (0.0948P)²] where P = (F_o² + 2F_c²)/3
2033 reflections	(Δ/σ)_max = 0.006
154 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₁H₉N₃O₃	V = 1057.4 (5) Å³
M_r = 231.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.852 (3) Å	µ = 0.11 mm⁻¹
b = 3.8000 (12) Å	T = 296 K
c = 17.721 (4) Å	0.21 × 0.19 × 0.17 mm
β = 97.89 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2033 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	619 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.982	R_int = 0.063
3497 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 0.73	Δρ_max = 0.24 e Å⁻³
2033 reflections	Δρ_min = −0.23 e Å⁻³
154 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.5620 (4)	−0.1566 (18)	0.1304 (3)	0.089 (2)
H1	0.5467	−0.2470	0.0817	0.107*
C2	0.6396 (4)	−0.0571 (18)	0.1574 (4)	0.085 (2)
H2A	0.6878	−0.0666	0.1328	0.103*
C3	0.6342 (3)	0.0688 (15)	0.2323 (3)	0.0609 (16)
H3	0.6781	0.1673	0.2659	0.073*
C4	0.5541 (3)	0.0181 (15)	0.2450 (3)	0.0554 (14)
C5	0.5169 (3)	0.1022 (14)	0.3106 (2)	0.0508 (14)
H5	0.5500	0.2188	0.3502	0.061*
C6	0.3320 (2)	0.0389 (13)	0.3999 (2)	0.0447 (13)
C7	0.2756 (2)	−0.1246 (13)	0.3415 (3)	0.0521 (14)
H7	0.2938	−0.1806	0.2952	0.063*
C8	0.1937 (3)	−0.2002 (14)	0.3537 (3)	0.0560 (14)
H8	0.1574	−0.3116	0.3154	0.067*
C9	0.1634 (3)	−0.1163 (15)	0.4210 (3)	0.0591 (15)
H9	0.1071	−0.1636	0.4269	0.071*
C10	0.2168 (3)	0.0365 (14)	0.4787 (3)	0.0555 (14)
H10	0.1979	0.0861	0.5250	0.067*
C11	0.3009 (2)	0.1184 (13)	0.4672 (2)	0.0446 (12)
N1	0.4392 (2)	0.0254 (11)	0.3182 (2)	0.0509 (11)
N2	0.4128 (2)	0.1163 (11)	0.3862 (2)	0.0499 (11)
H2	0.4473	0.2227	0.4205	0.060*
N3	0.3518 (2)	0.2903 (12)	0.5299 (2)	0.0535 (12)
O1	0.42600 (19)	0.3693 (10)	0.52361 (17)	0.0679 (11)
O2	0.32065 (19)	0.3559 (12)	0.58821 (19)	0.0776 (13)
O3	0.5066 (2)	−0.1130 (12)	0.1815 (2)	0.0797 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.111 (5)	0.101 (6)	0.059 (4)	0.020 (5)	0.027 (4)	−0.012 (4)
C2	0.081 (4)	0.086 (5)	0.095 (5)	0.018 (4)	0.035 (4)	0.020 (5)
C3	0.046 (3)	0.072 (4)	0.065 (4)	−0.005 (3)	0.008 (2)	−0.002 (3)
C4	0.048 (3)	0.073 (4)	0.042 (3)	0.014 (3)	−0.003 (2)	−0.003 (3)
C5	0.052 (3)	0.055 (4)	0.042 (3)	0.010 (3)	−0.006 (2)	−0.007 (3)
C6	0.044 (2)	0.047 (3)	0.039 (3)	0.005 (3)	−0.009 (2)	−0.003 (3)
C7	0.051 (3)	0.057 (4)	0.044 (3)	0.000 (3)	−0.011 (2)	−0.001 (3)
C8	0.051 (3)	0.059 (4)	0.051 (3)	−0.004 (3)	−0.016 (2)	−0.008 (3)
C9	0.040 (2)	0.070 (4)	0.064 (3)	−0.002 (3)	−0.006 (2)	−0.001 (3)
C10	0.056 (3)	0.061 (4)	0.045 (3)	0.003 (3)	−0.005 (2)	0.001 (3)
C11	0.040 (2)	0.053 (3)	0.037 (3)	−0.003 (3)	−0.0077 (19)	−0.002 (3)
N1	0.046 (2)	0.063 (3)	0.042 (2)	0.004 (2)	−0.0018 (16)	−0.008 (2)
N2	0.042 (2)	0.067 (3)	0.039 (2)	−0.003 (2)	−0.0005 (16)	−0.007 (2)
N3	0.046 (2)	0.077 (3)	0.035 (2)	0.005 (2)	−0.0035 (18)	−0.007 (2)
O1	0.0486 (18)	0.107 (3)	0.045 (2)	−0.016 (2)	−0.0029 (14)	−0.015 (2)
O2	0.0599 (19)	0.127 (4)	0.043 (2)	−0.003 (2)	−0.0027 (15)	−0.024 (2)
O3	0.072 (2)	0.104 (4)	0.060 (2)	0.006 (2)	−0.0034 (18)	−0.006 (3)

Geometric parameters (Å, º) top

C1—C2	1.313 (8)	C7—C8	1.376 (5)
C1—O3	1.355 (6)	C7—H7	0.9300
C1—H1	0.9300	C8—C9	1.383 (6)
C2—C3	1.426 (7)	C8—H8	0.9300
C2—H2A	0.9300	C9—C10	1.363 (6)
C3—C4	1.334 (6)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.412 (5)
C4—O3	1.360 (5)	C10—H10	0.9300
C4—C5	1.409 (5)	C11—N3	1.437 (5)
C5—N1	1.292 (5)	N1—N2	1.373 (4)
C5—H5	0.9300	N2—H2	0.8600
C6—N2	1.367 (5)	N3—O2	1.230 (4)
C6—C11	1.386 (6)	N3—O1	1.234 (4)
C6—C7	1.415 (6)

C2—C1—O3	112.5 (6)	C7—C8—C9	122.3 (4)
C2—C1—H1	123.7	C7—C8—H8	118.8
O3—C1—H1	123.7	C9—C8—H8	118.8
C1—C2—C3	105.2 (5)	C10—C9—C8	119.4 (4)
C1—C2—H2A	127.4	C10—C9—H9	120.3
C3—C2—H2A	127.4	C8—C9—H9	120.3
C4—C3—C2	106.8 (5)	C9—C10—C11	119.2 (5)
C4—C3—H3	126.6	C9—C10—H10	120.4
C2—C3—H3	126.6	C11—C10—H10	120.4
C3—C4—O3	110.2 (4)	C6—C11—C10	122.0 (4)
C3—C4—C5	128.4 (5)	C6—C11—N3	122.5 (4)
O3—C4—C5	121.2 (4)	C10—C11—N3	115.5 (4)
N1—C5—C4	123.3 (4)	C5—N1—N2	116.5 (4)
N1—C5—H5	118.4	C6—N2—N1	120.4 (4)
C4—C5—H5	118.4	C6—N2—H2	119.8
N2—C6—C11	123.9 (4)	N1—N2—H2	119.8
N2—C6—C7	118.6 (4)	O2—N3—O1	121.6 (4)
C11—C6—C7	117.5 (4)	O2—N3—C11	119.6 (4)
C8—C7—C6	119.4 (5)	O1—N3—C11	118.8 (4)
C8—C7—H7	120.3	C1—O3—C4	105.2 (4)
C6—C7—H7	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.98	2.599 (5)	128
C2—H2A···O2ⁱ	0.93	2.48	3.360 (7)	158

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₉N₃O₃
M_r	231.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	15.852 (3), 3.8000 (12), 17.721 (4)
β (°)	97.89 (2)
V (Å³)	1057.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.21 × 0.19 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.979, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	3497, 2033, 619
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.195, 0.73
No. of reflections	2033
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997); PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.98	2.599 (5)	127.6
C2—H2A···O2ⁱ	0.93	2.48	3.360 (7)	157.5

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Acknowledgements

The authors would like to express their deep appreciation to the startup fund for PhDs of the Natural Scientific Research of Zhengzhou University of Light Industry (No. 2005001) and the Fund for Natural Scientific Research of Zhengzhou University of Light Industry (000455).

References

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