(E)-N′-(2-Hy­droxy­benzyl­idene)furan-2-carbohydrazide

Bikas, R.; Hosseini Monfared, H.; Kazak, C.; Arslan, N.B.; Bijanzad, K.

doi:10.1107/S1600536810024839

organic compounds

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Volume 66| Part 8| August 2010| Page o2015

https://doi.org/10.1107/S1600536810024839

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(E)-N′-(2-Hydroxybenzylidene)furan-2-carbohydrazide

Rahman Bikas,^a ^* Hassan Hosseini Monfared,^a Canan Kazak,^b N. Burcu Arslan ^b and Keyvan Bijanzad ^c

^aDepartment of Chemistry, Zanjan University, 45195-313 Zanjan, Iran, ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55019 Kurupelit, Samsun, Turkey, and ^cFaculty of Chemistry, Iran University of Science and Technology (IUST), 16846 Tehran, Iran
^*Correspondence e-mail: bikas_r@yahoo.com

(Received 18 May 2010; accepted 24 June 2010; online 14 July 2010)

In the title compound, C₁₂H₁₀N₂O₃, the dihedral angle between the benzene ring and the furan ring is 16.12 (13)°. The conformation is stabilized by an intramolecular O—H⋯N hydrogen bond. Intermolecular N—H⋯O hydrogen bonds with the keto group as acceptor lead to strands along [001]. The molecule displays a trans configuration with respect to the C=N and N—N bonds.

Related literature

For historical background to aroylhydrazones, see: Offe et al. (1952 ); Craliz et al. (1955 ); Pickart et al. (1983 ); Arapov et al. (1987 ); Ranford et al. (1998 ); Savanini et al. (2002 ). For related structures, see: Monfared et al. (2010 ); Ali et al. (2005 ); Li et al. (2007 ); Diao et al. (2007 ).

Experimental

Crystal data

C₁₂H₁₀N₂O₃
M_r = 230.22
Orthorhombic, P c a 2₁
a = 17.3539 (15) Å
b = 6.3320 (4) Å
c = 9.8613 (7) Å
V = 1083.61 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.46 × 0.29 × 0.20 mm

Data collection

Stoe IPDS 2 diffractometer
6705 measured reflections
1130 independent reflections
792 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.043
S = 0.81
1130 reflections
159 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.21	2.900 (2)	137
O1—H22⋯N1	0.90 (3)	1.89 (3)	2.651 (3)	141 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810024839/vm2028sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810024839/vm2028Isup2.hkl

checkCIF report

Comment top

As part of our studies on the synthesis and characterization of aroylhydrazone derivatives, we report the crystal structure of (E)—N'-(2-hydroxybenzylidene)furan-2-carbohydrazide.

The asymmetric unit contains one molecule of the title compound, which is shown in Figure 1. The molecule is almost planar with a dihedral angle of 16.12 (13)° between the benzene ring and the furan ring. This configuration is stabilized by an intramolecular O—H···N hydrogen bond, with the nitrogen of the azomethine group (–C=N–) acting as acceptor. Intermolecular N—H···O hydrogen bonds with the keto group as acceptor lead to strands along [001] (Fig. 2).

Related literature top

For historical background to aroylhydrazones, see: Offe et al. (1952); Craliz et al. (1955); Pickart et al. (1983); Arapov et al. (1987); Ranford et al. (1998); Savanini et al. (2002). For related structures, see: Monfared et al. (2010); Ali et al. (2005); Li et al. (2007); Diao et al. (2007).

Experimental top

All reagents were commercially available and used as received. A methanol (10 ml) solution of 2-hydroxybenzaldehyde (1.5 mmol) was drop-wise added to a methanol solution (10 ml) of 2-furanecarboxylic acid hydrazide (1.5 mmol), and the mixture was refluxed for 3 h. Then the solution was evaporated on a steam bath to 5 cm³ and cooled to room temperature. Light yellow precipitates of the title compound were separated and filtered off, washed with 3 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 78%, mp 191 °C.

Structure description top

As part of our studies on the synthesis and characterization of aroylhydrazone derivatives, we report the crystal structure of (E)—N'-(2-hydroxybenzylidene)furan-2-carbohydrazide.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms. The dashed line indicates intramolecular O–H···N hydrogen bond.
	Fig. 2. View of the unit cell of the title compound viewed along [010]. Hydrogen bonds are drawn as dashed lines.

(E)-N'-(2-Hydroxybenzylidene)furan-2-carbohydrazide top

Crystal data top

C₁₂H₁₀N₂O₃	F(000) = 480
M_r = 230.22	D_x = 1.411 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6480 reflections
a = 17.3539 (15) Å	θ = 2.1–26.9°
b = 6.3320 (4) Å	µ = 0.10 mm⁻¹
c = 9.8613 (7) Å	T = 293 K
V = 1083.61 (14) Å³	Prism, light yellow
Z = 4	0.46 × 0.29 × 0.20 mm

Data collection top

Stoe IPDS 2 diffractometer	792 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.056
Graphite monochromator	θ_max = 26.0°, θ_min = 2.4°
Detector resolution: 6.67 pixels mm^-1	h = −21→21
w scans	k = −6→7
6705 measured reflections	l = −11→12
1130 independent reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.043	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ²(F_o²) + (0.0138P)²] where P = (F_o² + 2F_c²)/3
1130 reflections	(Δ/σ)_max < 0.001
159 parameters	Δρ_max = 0.10 e Å⁻³
3 restraints	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₁₂H₁₀N₂O₃	V = 1083.61 (14) Å³
M_r = 230.22	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 17.3539 (15) Å	µ = 0.10 mm⁻¹
b = 6.3320 (4) Å	T = 293 K
c = 9.8613 (7) Å	0.46 × 0.29 × 0.20 mm

Data collection top

Stoe IPDS 2 diffractometer	792 reflections with I > 2σ(I)
6705 measured reflections	R_int = 0.056
1130 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	3 restraints
wR(F²) = 0.043	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.10 e Å⁻³
1130 reflections	Δρ_min = −0.11 e Å⁻³
159 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
C1	0.44074 (10)	0.4371 (3)	0.5468 (2)	0.0396 (5)
C2	0.43426 (12)	0.2756 (4)	0.6432 (2)	0.0459 (6)
C3	0.48301 (13)	0.1039 (4)	0.6372 (3)	0.0594 (7)
H3	0.4781	−0.0039	0.7006	0.071*
C4	0.53899 (13)	0.0898 (4)	0.5384 (3)	0.0616 (7)
H4	0.5710	−0.0278	0.5349	0.074*
C5	0.54754 (12)	0.2496 (4)	0.4452 (3)	0.0579 (7)
H5	0.5859	0.2417	0.3796	0.070*
C6	0.49918 (11)	0.4207 (4)	0.4496 (3)	0.0496 (6)
H6	0.5054	0.5285	0.3865	0.060*
C7	0.38950 (11)	0.6177 (4)	0.5438 (2)	0.0461 (6)
H7	0.3928	0.7123	0.4718	0.055*
C8	0.25245 (13)	0.9022 (4)	0.7261 (2)	0.0447 (5)
C9	0.21197 (12)	1.0979 (4)	0.6958 (2)	0.0449 (6)
C10	0.16454 (13)	1.2205 (4)	0.7684 (3)	0.0569 (6)
H10	0.1472	1.1948	0.8561	0.068*
C11	0.14591 (15)	1.3964 (4)	0.6865 (3)	0.0626 (8)
H11	0.1139	1.5085	0.7097	0.075*
C12	0.18302 (13)	1.3702 (4)	0.5694 (3)	0.0607 (7)
H12	0.1808	1.4634	0.4966	0.073*
N1	0.33997 (9)	0.6505 (3)	0.63712 (19)	0.0455 (5)
N2	0.29468 (9)	0.8264 (3)	0.62150 (19)	0.0489 (5)
H2	0.2931	0.8892	0.5442	0.059*
O1	0.38068 (10)	0.2824 (3)	0.74331 (17)	0.0594 (5)
O2	0.24940 (11)	0.8172 (2)	0.83793 (16)	0.0575 (4)
O3	0.22438 (8)	1.1887 (3)	0.57132 (16)	0.0557 (4)
H22	0.3504 (17)	0.397 (4)	0.736 (3)	0.095 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0403 (11)	0.0426 (14)	0.0360 (12)	−0.0038 (10)	−0.0032 (11)	−0.0029 (12)
C2	0.0445 (12)	0.0538 (16)	0.0395 (13)	−0.0066 (11)	−0.0031 (12)	−0.0030 (13)
C3	0.0668 (15)	0.0509 (16)	0.0604 (17)	0.0002 (14)	−0.0073 (15)	0.0084 (14)
C4	0.0566 (14)	0.0627 (18)	0.0653 (18)	0.0127 (13)	−0.0034 (15)	−0.0040 (18)
C5	0.0463 (14)	0.074 (2)	0.0536 (16)	0.0036 (13)	0.0022 (13)	−0.0168 (15)
C6	0.0493 (14)	0.0584 (16)	0.0412 (15)	−0.0033 (13)	0.0019 (11)	0.0001 (15)
C7	0.0469 (11)	0.0547 (16)	0.0366 (12)	−0.0040 (11)	0.0014 (12)	0.0014 (11)
C8	0.0444 (12)	0.0533 (14)	0.0364 (13)	0.0000 (12)	−0.0023 (10)	−0.0041 (14)
C9	0.0428 (12)	0.0559 (15)	0.0360 (13)	0.0037 (12)	−0.0005 (10)	−0.0039 (13)
C10	0.0599 (14)	0.0665 (18)	0.0444 (14)	0.0099 (15)	0.0048 (13)	−0.0046 (14)
C11	0.0652 (17)	0.0651 (18)	0.0576 (17)	0.0197 (14)	−0.0024 (13)	−0.0115 (16)
C12	0.0649 (15)	0.0568 (19)	0.0604 (17)	0.0135 (13)	−0.0125 (14)	0.0000 (15)
N1	0.0450 (10)	0.0506 (13)	0.0409 (10)	0.0042 (9)	0.0020 (10)	−0.0045 (10)
N2	0.0587 (10)	0.0532 (12)	0.0349 (11)	0.0110 (10)	0.0020 (10)	−0.0009 (10)
O1	0.0615 (10)	0.0708 (13)	0.0459 (10)	−0.0058 (10)	0.0095 (9)	0.0086 (10)
O2	0.0702 (10)	0.0643 (10)	0.0382 (10)	0.0069 (9)	0.0059 (9)	0.0018 (9)
O3	0.0592 (10)	0.0644 (11)	0.0434 (10)	0.0118 (8)	0.0015 (8)	0.0016 (10)

Geometric parameters (Å, º) top

C1—C6	1.399 (3)	C8—O2	1.228 (3)
C1—C2	1.401 (3)	C8—N2	1.354 (3)
C1—C7	1.449 (3)	C8—C9	1.456 (3)
C2—O1	1.357 (3)	C9—C10	1.339 (3)
C2—C3	1.379 (3)	C9—O3	1.372 (3)
C3—C4	1.378 (3)	C10—C11	1.413 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.375 (4)	C11—C12	1.332 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.371 (3)	C12—O3	1.355 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	N1—N2	1.371 (2)
C7—N1	1.277 (3)	N2—H2	0.8600
C7—H7	0.9300	O1—H22	0.90 (3)

C6—C1—C2	117.9 (2)	O2—C8—N2	123.5 (2)
C6—C1—C7	119.3 (2)	O2—C8—C9	122.5 (2)
C2—C1—C7	122.75 (19)	N2—C8—C9	114.0 (2)
O1—C2—C3	118.5 (2)	C10—C9—O3	109.4 (2)
O1—C2—C1	121.7 (2)	C10—C9—C8	132.8 (2)
C3—C2—C1	119.8 (2)	O3—C9—C8	117.72 (19)
C4—C3—C2	120.9 (2)	C9—C10—C11	106.9 (2)
C4—C3—H3	119.5	C9—C10—H10	126.5
C2—C3—H3	119.5	C11—C10—H10	126.5
C5—C4—C3	120.0 (2)	C12—C11—C10	106.7 (2)
C5—C4—H4	120.0	C12—C11—H11	126.7
C3—C4—H4	120.0	C10—C11—H11	126.7
C6—C5—C4	119.6 (2)	C11—C12—O3	110.5 (2)
C6—C5—H5	120.2	C11—C12—H12	124.8
C4—C5—H5	120.2	O3—C12—H12	124.8
C5—C6—C1	121.6 (2)	C7—N1—N2	115.92 (19)
C5—C6—H6	119.2	C8—N2—N1	120.84 (19)
C1—C6—H6	119.2	C8—N2—H2	119.6
N1—C7—C1	121.8 (2)	N1—N2—H2	119.6
N1—C7—H7	119.1	C2—O1—H22	111.8 (19)
C1—C7—H7	119.1	C12—O3—C9	106.5 (2)

C6—C1—C2—O1	178.0 (2)	N2—C8—C9—C10	179.1 (2)
C7—C1—C2—O1	−2.3 (3)	O2—C8—C9—O3	174.7 (2)
C6—C1—C2—C3	−2.2 (3)	N2—C8—C9—O3	−3.9 (3)
C7—C1—C2—C3	177.5 (2)	O3—C9—C10—C11	0.1 (3)
O1—C2—C3—C4	−179.3 (2)	C8—C9—C10—C11	177.4 (2)
C1—C2—C3—C4	0.9 (3)	C9—C10—C11—C12	0.0 (3)
C2—C3—C4—C5	0.9 (4)	C10—C11—C12—O3	−0.1 (3)
C3—C4—C5—C6	−1.2 (4)	C1—C7—N1—N2	−179.55 (19)
C4—C5—C6—C1	−0.2 (3)	O2—C8—N2—N1	−2.7 (3)
C2—C1—C6—C5	1.9 (3)	C9—C8—N2—N1	175.82 (18)
C7—C1—C6—C5	−177.8 (2)	C7—N1—N2—C8	−165.59 (19)
C6—C1—C7—N1	−173.37 (19)	C11—C12—O3—C9	0.2 (3)
C2—C1—C7—N1	6.9 (3)	C10—C9—O3—C12	−0.2 (2)
O2—C8—C9—C10	−2.3 (4)	C8—C9—O3—C12	−177.90 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.21	2.900 (2)	137
O1—H22···N1	0.90 (3)	1.89 (3)	2.651 (3)	141 (3)

Symmetry code: (i) −x+1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂O₃
M_r	230.22
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	17.3539 (15), 6.3320 (4), 9.8613 (7)
V (Å³)	1083.61 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.46 × 0.29 × 0.20

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6705, 1130, 792
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.043, 0.81
No. of reflections	1130
No. of parameters	159
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.11

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.21	2.900 (2)	136.9
O1—H22···N1	0.90 (3)	1.89 (3)	2.651 (3)	141 (3)

Symmetry code: (i) −x+1/2, y, z−1/2.

Acknowledgements

The authors are grateful to Zanjan University and Ondokuz Mayis University.

References

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