N′-(Furan-2-ylmethyl­ene)-2-hydroxy­benzohydrazide

Zhang, Y.-X.

doi:10.1107/S1600536808034636

organic compounds

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Volume 64| Part 11| November 2008| Page o2208

doi:10.1107/S1600536808034636

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N′-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide

Yan-Xia Zhang ^a ^*

^aDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: zhangyanxia@mail.sdu.edu.cn

(Received 20 October 2008; accepted 23 October 2008; online 25 October 2008)

In the title molecule, C₁₂H₁₀N₂O₃, the aromatic and furan rings form a dihedral angle of 8.89 (1)° and an intramolecular N—H⋯O hydrogen bond occurs. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into zigzag chains running along the c axis.

Related literature

For background on Schiff bases, see: Garnovskii et al. (1993 ); Anderson et al. (1997 ); Musie et al., (2001 ); Paul et al. (2002 ); Yang, (2006 ). For reference bond distances, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₀N₂O₃
M_r = 230.22
Monoclinic, P 2₁ /n
a = 4.9898 (5) Å
b = 20.662 (2) Å
c = 10.6994 (11) Å
β = 101.421 (2)°
V = 1081.24 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.98, T_max = 0.99
5631 measured reflections
1904 independent reflections
1451 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.02
1904 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	2.14	2.804 (2)	139
N1—H1A⋯O1	0.86	1.99	2.650 (2)	133
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034636/bg2220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034636/bg2220Isup2.hkl

checkCIF report

Comment top

Recently, a number of Schiff-bases have been investigated because of their coordination chemistry (Garnovskii et al., 1993; Musie et al., 2001; Paul et al., 2002; Yang, 2006;) and biological systems (Anderson et al., 1997). In order to search for new Schiff-bases with higher bioactivity, the title compound, (I), was synthesized and its crystal structure determined. In (I) (Fig. 1), the bond lengths and angles are in good agreement with the expected values (Allen et al., 1987). In the crystal structure (Fig. 2), the molecules are linked into infinite chains by O—H···O hydrogen bonds. There is also an intramolecular N—H···O hydrogen bond.

Related literature top

For Schiff bases, see: Garnovskii et al. (1993); Anderson et al. (1997); Musie et al., (2001); Paul et al. (2002); Yang, (2006). For reference bond distances, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by the reaction of 2-hydroxy-benzoic acid hydrazide(1 mmol, 152.2 mg) with furan-2-carbaldehyde(1 mmol, 96.2 mg) in ethanol(20 ml) under reflux conditions (348 K) for 5 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After six days orange crystals suitable for the X-ray diffraction study were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The structure of the infinite chains formed via hydrogen bonds, H atoms have been omitted for clarity. Dashed lines indicate hydrogen bonds.

N'-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide top

Crystal data top

C₁₂H₁₀N₂O₃	F(000) = 480
M_r = 230.22	D_x = 1.414 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1748 reflections
a = 4.9898 (5) Å	θ = 2.2–25.0°
b = 20.662 (2) Å	µ = 0.10 mm⁻¹
c = 10.6994 (11) Å	T = 295 K
β = 101.421 (2)°	Block, orange
V = 1081.24 (19) Å³	0.12 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	1904 independent reflections
Radiation source: fine-focus sealed tube	1451 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
T_min = 0.98, T_max = 0.99	k = −24→21
5631 measured reflections	l = −11→12

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0472P)² + 0.1418P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
1904 reflections	Δρ_max = 0.12 e Å⁻³
156 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0107 (19)

Crystal data top

C₁₂H₁₀N₂O₃	V = 1081.24 (19) Å³
M_r = 230.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.9898 (5) Å	µ = 0.10 mm⁻¹
b = 20.662 (2) Å	T = 295 K
c = 10.6994 (11) Å	0.12 × 0.10 × 0.06 mm
β = 101.421 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	1904 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1451 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.99	R_int = 0.023
5631 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.02	Δρ_max = 0.12 e Å⁻³
1904 reflections	Δρ_min = −0.13 e Å⁻³
156 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
O1	0.2921 (2)	0.22463 (6)	0.59528 (10)	0.0611 (4)
H1	0.3615	0.2261	0.5320	0.092*
O2	0.2021 (2)	0.22907 (5)	0.97330 (9)	0.0541 (3)
O3	−0.6276 (3)	0.42331 (7)	0.68440 (12)	0.0815 (4)
N1	0.0370 (2)	0.26559 (6)	0.77544 (11)	0.0435 (3)
H1A	0.0365	0.2638	0.6951	0.052*
N2	−0.1342 (2)	0.30720 (6)	0.82213 (11)	0.0422 (3)
C1	0.4351 (3)	0.18305 (7)	0.68139 (14)	0.0415 (4)
C2	0.3961 (3)	0.18397 (7)	0.80733 (13)	0.0385 (3)
C3	0.5525 (3)	0.14165 (7)	0.89334 (15)	0.0493 (4)
H3	0.5312	0.1417	0.9778	0.059*
C4	0.7373 (3)	0.09972 (8)	0.85745 (16)	0.0560 (4)
H4	0.8409	0.0723	0.9171	0.067*
C5	0.7674 (3)	0.09876 (8)	0.73201 (16)	0.0549 (4)
H5	0.8892	0.0699	0.7065	0.066*
C6	0.6191 (3)	0.14000 (8)	0.64527 (15)	0.0508 (4)
H6	0.6417	0.1392	0.5611	0.061*
C7	0.2058 (3)	0.22765 (7)	0.85884 (13)	0.0397 (4)
C8	−0.2876 (3)	0.34231 (7)	0.74000 (15)	0.0483 (4)
H8	−0.2834	0.3378	0.6539	0.058*
C9	−0.4676 (3)	0.38898 (7)	0.77975 (14)	0.0460 (4)
C10	−0.5197 (3)	0.40836 (8)	0.89143 (17)	0.0582 (5)
H10	−0.4375	0.3928	0.9714	0.070*
C11	−0.7221 (4)	0.45682 (9)	0.8659 (2)	0.0668 (5)
H11	−0.7991	0.4793	0.9254	0.080*
C12	−0.7803 (4)	0.46390 (9)	0.7418 (2)	0.0767 (6)
H12	−0.9090	0.4928	0.6988	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0660 (8)	0.0871 (9)	0.0369 (6)	0.0281 (6)	0.0263 (5)	0.0161 (6)
O2	0.0647 (7)	0.0696 (8)	0.0325 (6)	0.0026 (6)	0.0206 (5)	0.0006 (5)
O3	0.0984 (10)	0.0848 (9)	0.0550 (8)	0.0339 (8)	0.0000 (7)	−0.0057 (7)
N1	0.0502 (7)	0.0512 (7)	0.0328 (7)	0.0022 (6)	0.0171 (6)	−0.0049 (6)
N2	0.0457 (7)	0.0457 (7)	0.0386 (7)	−0.0034 (6)	0.0167 (6)	−0.0075 (6)
C1	0.0397 (8)	0.0502 (9)	0.0365 (8)	−0.0013 (7)	0.0120 (6)	0.0019 (7)
C2	0.0386 (8)	0.0434 (8)	0.0350 (7)	−0.0083 (6)	0.0107 (6)	−0.0015 (6)
C3	0.0566 (9)	0.0529 (9)	0.0388 (8)	−0.0027 (8)	0.0103 (7)	0.0013 (7)
C4	0.0582 (10)	0.0533 (10)	0.0538 (10)	0.0060 (8)	0.0046 (8)	0.0067 (8)
C5	0.0525 (10)	0.0530 (10)	0.0612 (11)	0.0058 (8)	0.0162 (8)	−0.0053 (8)
C6	0.0512 (9)	0.0611 (10)	0.0439 (9)	0.0048 (8)	0.0185 (7)	−0.0016 (8)
C7	0.0427 (8)	0.0450 (8)	0.0343 (8)	−0.0099 (7)	0.0146 (6)	−0.0019 (7)
C8	0.0584 (10)	0.0526 (9)	0.0362 (8)	−0.0008 (8)	0.0147 (8)	−0.0076 (7)
C9	0.0475 (9)	0.0461 (9)	0.0439 (9)	−0.0030 (7)	0.0080 (7)	−0.0032 (7)
C10	0.0629 (11)	0.0656 (11)	0.0506 (10)	0.0079 (9)	0.0220 (8)	−0.0004 (8)
C11	0.0634 (12)	0.0592 (11)	0.0856 (15)	0.0003 (9)	0.0337 (11)	−0.0125 (10)
C12	0.0694 (13)	0.0596 (12)	0.0966 (17)	0.0202 (10)	0.0055 (12)	−0.0088 (11)

Geometric parameters (Å, º) top

O1—C1	1.3549 (17)	C3—H3	0.9300
O1—H1	0.8200	C4—C5	1.380 (2)
O2—C7	1.2288 (16)	C4—H4	0.9300
O3—C12	1.359 (2)	C5—C6	1.365 (2)
O3—C9	1.3633 (19)	C5—H5	0.9300
N1—C7	1.3503 (18)	C6—H6	0.9300
N1—N2	1.3737 (16)	C8—C9	1.438 (2)
N1—H1A	0.8600	C8—H8	0.9300
N2—C8	1.2720 (19)	C9—C10	1.334 (2)
C1—C6	1.387 (2)	C10—C11	1.410 (2)
C1—C2	1.3991 (19)	C10—H10	0.9300
C2—C3	1.391 (2)	C11—C12	1.310 (3)
C2—C7	1.492 (2)	C11—H11	0.9300
C3—C4	1.374 (2)	C12—H12	0.9300

C1—O1—H1	109.5	C5—C6—C1	120.69 (15)
C12—O3—C9	106.28 (15)	C5—C6—H6	119.7
C7—N1—N2	118.33 (11)	C1—C6—H6	119.7
C7—N1—H1A	120.8	O2—C7—N1	120.95 (13)
N2—N1—H1A	120.8	O2—C7—C2	121.25 (13)
C8—N2—N1	115.98 (12)	N1—C7—C2	117.81 (12)
O1—C1—C6	120.38 (13)	N2—C8—C9	120.25 (13)
O1—C1—C2	119.43 (13)	N2—C8—H8	119.9
C6—C1—C2	120.19 (14)	C9—C8—H8	119.9
C3—C2—C1	117.51 (14)	C10—C9—O3	108.97 (14)
C3—C2—C7	116.76 (12)	C10—C9—C8	135.24 (16)
C1—C2—C7	125.71 (13)	O3—C9—C8	115.78 (14)
C4—C3—C2	122.05 (14)	C9—C10—C11	107.40 (17)
C4—C3—H3	119.0	C9—C10—H10	126.3
C2—C3—H3	119.0	C11—C10—H10	126.3
C3—C4—C5	119.29 (15)	C12—C11—C10	106.37 (17)
C3—C4—H4	120.4	C12—C11—H11	126.8
C5—C4—H4	120.4	C10—C11—H11	126.8
C6—C5—C4	120.24 (15)	C11—C12—O3	110.96 (17)
C6—C5—H5	119.9	C11—C12—H12	124.5
C4—C5—H5	119.9	O3—C12—H12	124.5

C7—N1—N2—C8	179.41 (13)	C3—C2—C7—O2	4.9 (2)
O1—C1—C2—C3	−178.33 (13)	C1—C2—C7—O2	−173.54 (14)
C6—C1—C2—C3	1.5 (2)	C3—C2—C7—N1	−175.00 (13)
O1—C1—C2—C7	0.1 (2)	C1—C2—C7—N1	6.6 (2)
C6—C1—C2—C7	179.90 (13)	N1—N2—C8—C9	−177.93 (12)
C1—C2—C3—C4	−0.6 (2)	C12—O3—C9—C10	−0.45 (19)
C7—C2—C3—C4	−179.16 (13)	C12—O3—C9—C8	179.81 (14)
C2—C3—C4—C5	−0.8 (2)	N2—C8—C9—C10	1.6 (3)
C3—C4—C5—C6	1.4 (3)	N2—C8—C9—O3	−178.74 (14)
C4—C5—C6—C1	−0.5 (2)	O3—C9—C10—C11	0.28 (19)
O1—C1—C6—C5	178.84 (14)	C8—C9—C10—C11	179.95 (17)
C2—C1—C6—C5	−1.0 (2)	C9—C10—C11—C12	0.0 (2)
N2—N1—C7—O2	1.8 (2)	C10—C11—C12—O3	−0.3 (2)
N2—N1—C7—C2	−178.36 (11)	C9—O3—C12—C11	0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.14	2.804 (2)	139
N1—H1A···O1	0.86	1.99	2.650 (2)	133

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₂O₃
M_r	230.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	4.9898 (5), 20.662 (2), 10.6994 (11)
β (°)	101.421 (2)
V (Å³)	1081.24 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.98, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	5631, 1904, 1451
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.02
No. of reflections	1904
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	2.14	2.804 (2)	138.6
N1—H1A···O1	0.86	1.99	2.650 (2)	132.8

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

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No. Y07–2–16).

References

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