3-Hydr­oxy-N′-(2-hydroxy­benzyl­idene)benzohydrazide

Peng, S.-J.; Hou, H.-Y.

doi:10.1107/S1600536808027426

organic compounds

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Volume 64| Part 10| October 2008| Page o1864

doi:10.1107/S1600536808027426

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3-Hydroxy-N′-(2-hydroxybenzylidene)benzohydrazide

San-Jun Peng ^a ^* and Hai-Yun Hou ^b

^aCollege of Chemistry and Biological Engineering, Changsha University of Science and Technology, Changsha 410076, People's Republic of China, and ^bCollege of Environmental and Chemical Engineering, Xi'an Polytechnic University, Xi'an 710048, People's Republic of China
^*Correspondence e-mail: sanjunpeng@163.com

(Received 13 August 2008; accepted 26 August 2008; online 6 September 2008)

The title compound, C₁₄H₁₂N₂O₃, was synthesized by the condensation of salicylaldehyde with 3-hydroxybenzohydrazide. The dihedral angle between the two benzene rings is 12.4 (2)°. The 2-hydroxy group forms an intramolecular O—H⋯N hydrogen bond with the imide N atom. Molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds into a two-dimensional polymeric structure parallel to the ab plane.

Related literature

For related literature, see: Ali et al. (2005 ); Eltayeb et al. (2008 ); Habibi et al. (2007 ); Jing et al. (2006 ); Ling et al. (2008 ); Peng & You (2007 ); Peng & Zhou (2007 ); Peng, Ping & Song (2007 ); Peng, Yang & Zhou (2006 ); Peng, Zhou & Yang (2006 ); Yehye et al. (2008a ,b ).

Experimental

Crystal data

C₁₄H₁₂N₂O₃
M_r = 256.26
Orthorhombic, P b c a
a = 14.405 (2) Å
b = 9.661 (1) Å
c = 17.905 (2) Å
V = 2491.8 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.978, T_max = 0.981
13415 measured reflections
2720 independent reflections
1869 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 1.03
2720 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.6010 (19)	146
O3—H3⋯O2ⁱ	0.82	1.81	2.5946 (16)	159
N2—H2⋯O3ⁱⁱ	0.895 (9)	2.119 (10)	3.0062 (18)	171.0 (18)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536808027426/gk2164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027426/gk2164Isup2.hkl

checkCIF report

Comment top

Schiff bases derived from the condensation of aldehydes with primary amines play an important role in coordination chemistry (Ali et al., 2005; Eltayeb et al., 2008; Habibi et al., 2007). Recently, we have reported synthesis and crystal structure of some Schiff base complexes (Peng, Yang & Zhou, 2006; Peng, Zhou & Yang, 2006; Peng et al., 2007; Peng & You, 2007; Peng & Zhou, 2007). We report herein the crystal structure of the title compound, Fig. 1.

All the bond lengths are comparable to those observed in other similar compounds (Yehye et al., 2008a,b; Jing et al., 2006; Ling et al., 2008). The molecule is not planar and the dihedral angle between the two benzene rings is 12.4 (2)°. There is an intramolecular O–H···N hydrogen bond (Table 1) in each molecule of the compound. The molecules are linked through intermolecular O–H···O and N–H···O hydrogen bonds (Table 1), forming layers parallel to the ab plane (Fig. 2).

Related literature top

For related literature, see: Ali et al. (2005); Eltayeb et al. (2008); Habibi et al. (2007); Jing et al. (2006); Ling et al. (2008); Peng & You (2007); Peng & Zhou (2007); Peng, Ping & Song (2007); Peng, Yang & Zhou (2006); Peng, Zhou & Yang (2006); Yehye et al. (2008a,b).

Experimental top

3-Hydroxybenzohydrazide (0.1 mmol, 15.2 mg) and salicylaldehyde (0.1 mmol, 12.2 mg) were stirred at 318 K in methanol (10 ml) for 30 min. The filtrate was kept open to slowly evaporate for a few days, depositing colorless block-like crystals of the title compound.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 the title compound, showing the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. Packing diagram, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

3-Hydroxy-N'-(2-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₂N₂O₃	F(000) = 1072
M_r = 256.26	D_x = 1.366 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3092 reflections
a = 14.405 (2) Å	θ = 2.7–26.0°
b = 9.661 (1) Å	µ = 0.10 mm⁻¹
c = 17.905 (2) Å	T = 298 K
V = 2491.8 (5) Å³	Block, colorless
Z = 8	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→18
T_min = 0.978, T_max = 0.981	k = −11→12
13415 measured reflections	l = −22→22

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0535P)² + 0.3997P] where P = (F_o² + 2F_c²)/3
2720 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₄H₁₂N₂O₃	V = 2491.8 (5) Å³
M_r = 256.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.405 (2) Å	µ = 0.10 mm⁻¹
b = 9.661 (1) Å	T = 298 K
c = 17.905 (2) Å	0.23 × 0.20 × 0.20 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2720 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1869 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.981	R_int = 0.039
13415 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.13 e Å⁻³
2720 reflections	Δρ_min = −0.18 e Å⁻³
177 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	0.16163 (8)	1.20579 (14)	0.04590 (8)	0.0677 (4)
H1	0.1829	1.1427	0.0713	0.102*
O2	0.33625 (7)	0.98665 (12)	0.15618 (6)	0.0524 (3)
O3	0.56381 (7)	0.66767 (12)	0.27314 (7)	0.0548 (3)
H3	0.5826	0.6036	0.2991	0.082*
N1	0.15527 (8)	0.98711 (13)	0.13048 (7)	0.0419 (3)
N2	0.19669 (8)	0.88568 (13)	0.17276 (8)	0.0436 (3)
C1	0.01929 (10)	1.09152 (16)	0.08195 (8)	0.0409 (4)
C2	0.06764 (12)	1.19810 (18)	0.04586 (9)	0.0493 (4)
C3	0.01833 (15)	1.3000 (2)	0.00834 (11)	0.0668 (5)
H3A	0.0501	1.3716	−0.0152	0.080*
C4	−0.07686 (16)	1.2964 (2)	0.00557 (11)	0.0709 (6)
H4	−0.1089	1.3653	−0.0200	0.085*
C5	−0.12534 (13)	1.1922 (2)	0.04022 (11)	0.0663 (6)
H5	−0.1898	1.1900	0.0380	0.080*
C6	−0.07735 (11)	1.0909 (2)	0.07839 (9)	0.0533 (4)
H6	−0.1102	1.0207	0.1022	0.064*
C7	0.06694 (10)	0.98419 (16)	0.12381 (9)	0.0423 (4)
H7	0.0331	0.9131	0.1458	0.051*
C8	0.28882 (10)	0.89504 (16)	0.18561 (8)	0.0411 (4)
C9	0.32990 (9)	0.78911 (16)	0.23665 (9)	0.0396 (4)
C10	0.42602 (10)	0.77388 (16)	0.23447 (9)	0.0402 (4)
H10	0.4612	0.8302	0.2033	0.048*
C11	0.46926 (9)	0.67575 (16)	0.27832 (9)	0.0407 (4)
C12	0.41777 (11)	0.59119 (18)	0.32492 (9)	0.0474 (4)
H12	0.4468	0.5240	0.3538	0.057*
C13	0.32267 (11)	0.6079 (2)	0.32798 (10)	0.0561 (5)
H13	0.2878	0.5519	0.3596	0.067*
C14	0.27860 (11)	0.70631 (19)	0.28484 (9)	0.0517 (4)
H14	0.2146	0.7172	0.2880	0.062*
H2	0.1622 (12)	0.8175 (16)	0.1921 (11)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0516 (7)	0.0702 (10)	0.0815 (10)	−0.0133 (6)	0.0067 (6)	0.0162 (7)
O2	0.0375 (6)	0.0518 (7)	0.0680 (8)	−0.0079 (5)	−0.0066 (5)	0.0050 (6)
O3	0.0286 (5)	0.0524 (7)	0.0835 (9)	0.0054 (5)	−0.0026 (5)	0.0072 (6)
N1	0.0331 (6)	0.0436 (8)	0.0488 (7)	0.0030 (5)	−0.0044 (5)	−0.0028 (6)
N2	0.0297 (6)	0.0423 (8)	0.0586 (8)	0.0007 (5)	−0.0060 (6)	0.0025 (6)
C1	0.0378 (8)	0.0462 (9)	0.0387 (8)	0.0039 (7)	−0.0007 (6)	−0.0018 (7)
C2	0.0507 (10)	0.0523 (10)	0.0448 (9)	−0.0009 (8)	0.0011 (7)	−0.0004 (8)
C3	0.0846 (15)	0.0592 (12)	0.0566 (11)	0.0036 (10)	0.0013 (10)	0.0144 (9)
C4	0.0794 (14)	0.0749 (14)	0.0583 (12)	0.0259 (11)	−0.0111 (11)	0.0105 (10)
C5	0.0491 (10)	0.0885 (15)	0.0614 (12)	0.0206 (10)	−0.0073 (9)	0.0031 (11)
C6	0.0401 (9)	0.0672 (12)	0.0525 (10)	0.0064 (8)	−0.0014 (7)	0.0054 (9)
C7	0.0359 (8)	0.0434 (9)	0.0476 (9)	−0.0005 (6)	0.0000 (7)	0.0001 (7)
C8	0.0312 (7)	0.0424 (9)	0.0497 (9)	−0.0003 (7)	−0.0027 (6)	−0.0081 (7)
C9	0.0286 (7)	0.0440 (9)	0.0461 (8)	−0.0005 (6)	−0.0040 (6)	−0.0075 (7)
C10	0.0296 (7)	0.0395 (8)	0.0516 (9)	−0.0022 (6)	0.0002 (6)	−0.0050 (7)
C11	0.0275 (7)	0.0417 (8)	0.0529 (9)	0.0026 (6)	−0.0050 (7)	−0.0113 (7)
C12	0.0414 (8)	0.0540 (10)	0.0467 (9)	0.0054 (7)	−0.0046 (7)	0.0004 (8)
C13	0.0394 (9)	0.0740 (13)	0.0548 (10)	−0.0012 (8)	0.0048 (7)	0.0130 (9)
C14	0.0282 (7)	0.0729 (12)	0.0541 (10)	0.0016 (7)	0.0006 (7)	0.0026 (9)

Geometric parameters (Å, º) top

O1—C2	1.356 (2)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.380 (3)
O2—C8	1.2360 (18)	C5—H5	0.9300
O3—C11	1.3673 (17)	C6—H6	0.9300
O3—H3	0.8200	C7—H7	0.9300
N1—C7	1.2784 (18)	C8—C9	1.494 (2)
N1—N2	1.3745 (18)	C9—C14	1.389 (2)
N2—C8	1.3499 (18)	C9—C10	1.3928 (19)
N2—H2	0.895 (9)	C10—C11	1.379 (2)
C1—C6	1.394 (2)	C10—H10	0.9300
C1—C2	1.401 (2)	C11—C12	1.383 (2)
C1—C7	1.452 (2)	C12—C13	1.380 (2)
C2—C3	1.388 (2)	C12—H12	0.9300
C3—C4	1.373 (3)	C13—C14	1.380 (2)
C3—H3A	0.9300	C13—H13	0.9300
C4—C5	1.373 (3)	C14—H14	0.9300

C2—O1—H1	109.5	N1—C7—C1	120.20 (14)
C11—O3—H3	109.5	N1—C7—H7	119.9
C7—N1—N2	117.88 (13)	C1—C7—H7	119.9
C8—N2—N1	118.21 (13)	O2—C8—N2	121.25 (14)
C8—N2—H2	122.0 (13)	O2—C8—C9	122.15 (13)
N1—N2—H2	119.8 (13)	N2—C8—C9	116.60 (13)
C6—C1—C2	118.60 (15)	C14—C9—C10	119.03 (14)
C6—C1—C7	119.53 (15)	C14—C9—C8	124.29 (13)
C2—C1—C7	121.86 (14)	C10—C9—C8	116.68 (13)
O1—C2—C3	118.19 (16)	C11—C10—C9	120.37 (14)
O1—C2—C1	122.45 (15)	C11—C10—H10	119.8
C3—C2—C1	119.36 (17)	C9—C10—H10	119.8
C4—C3—C2	120.71 (19)	O3—C11—C10	116.77 (14)
C4—C3—H3A	119.6	O3—C11—C12	122.77 (14)
C2—C3—H3A	119.6	C10—C11—C12	120.46 (13)
C3—C4—C5	120.68 (18)	C13—C12—C11	119.15 (15)
C3—C4—H4	119.7	C13—C12—H12	120.4
C5—C4—H4	119.7	C11—C12—H12	120.4
C4—C5—C6	119.29 (18)	C14—C13—C12	120.98 (16)
C4—C5—H5	120.4	C14—C13—H13	119.5
C6—C5—H5	120.4	C12—C13—H13	119.5
C5—C6—C1	121.34 (18)	C13—C14—C9	119.98 (14)
C5—C6—H6	119.3	C13—C14—H14	120.0
C1—C6—H6	119.3	C9—C14—H14	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.6010 (19)	146
O3—H3···O2ⁱ	0.82	1.81	2.5946 (16)	159
N2—H2···O3ⁱⁱ	0.90 (1)	2.12 (1)	3.0062 (18)	171 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₃
M_r	256.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	14.405 (2), 9.661 (1), 17.905 (2)
V (Å³)	2491.8 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.978, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	13415, 2720, 1869
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.119, 1.03
No. of reflections	2720
No. of parameters	177
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.6010 (19)	145.8
O3—H3···O2ⁱ	0.82	1.81	2.5946 (16)	159.0
N2—H2···O3ⁱⁱ	0.895 (9)	2.119 (10)	3.0062 (18)	171.0 (18)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, y, −z+1/2.

Acknowledgements

We acknowledge Changsha University of Science and Technology for research grants.

References

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