N′-(2,5-Dihydroxy­benzyl­idene)-2-hydr­oxy-3-methyl­benzohydrazide

Han, Y.-Y.; Li, Y.-H.; Zhao, Q.-R.

doi:10.1107/S1600536810013395

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1091

https://doi.org/10.1107/S1600536810013395

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N′-(2,5-Dihydroxybenzylidene)-2-hydroxy-3-methylbenzohydrazide

You-Yue Han,^a ^* Yong-Hong Li ^a and Qiu-Rong Zhao ^a

^aDepartment of Chemistry and Life Science, Chuzhou University, Chuzhou, Anhui 239000, People's Republic of China
^*Correspondence e-mail: hanyouyue@126.com

(Received 6 April 2010; accepted 11 April 2010; online 17 April 2010)

In the title compound, C₁₅H₁₄N₂O₄, the dihedral angle between the two benzene rings is 4.1 (2)°. The molecule adopts an E configuration with respect to the C=N bond. There are intramolecular O—H⋯N and O—H⋯O hydrogen bonds in the molecule. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 ); Cukurovali et al. (2006 ). For the crystal structures of hydrazones, see: Mohd Lair et al. (2009 ); Lin & Sang (2009 ); Suleiman Gwaram et al. (2010 ). For hydrazone compounds recently reported by us, see: Han & Zhao (2010a ,b ). For bond-length data, see: Allen et al. (1987 ). For similar compounds, see: Li & Ban (2009 ); Lo & Ng (2009 ); Ning & Xu (2009 ); Zhu et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Monoclinic, P 2₁ /c
a = 13.333 (2) Å
b = 7.316 (1) Å
c = 13.738 (2) Å
β = 94.742 (2)°
V = 1335.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.25 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.974, T_max = 0.977
7636 measured reflections
3002 independent reflections
1457 reflections with I > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.136
S = 0.82
3002 reflections
197 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.82	2.5452 (19)	147
O3—H3⋯N2	0.82	1.85	2.576 (2)	146
O4—H4⋯O3ⁱ	0.82	1.97	2.774 (2)	169
N1—H1A⋯O4ⁱⁱ	0.90 (2)	2.27 (2)	3.072 (2)	148 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810013395/om2333sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013395/om2333Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of the hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). As a continuation of our work on the structural characterization of such compounds (Han & Zhao, 2010a,b), the title new hydrazone compound is reported.

In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 4.1 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There are intramolecular O–H···N and O–H···O hydrogen bonds in the molecule (Table 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable with those in the similar compounds (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

Related literature top

For the biological properties of hydrazone compounds, see: Patil et al. (2010); Cukurovali et al. (2006). For the crystal structures of hydrazones, see: Mohd Lair et al. (2009); Lin & Sang (2009); Suleiman Gwaram et al. (2010). For hydrazone compounds recently reported by us, see: Han & Zhao (2010a,b). For bond-length data, see: Allen et al. (1987). For similar compounds, see: Li & Ban (2009); Lo & Ng (2009); Ning & Xu (2009); Zhu et al. (2009).

Experimental top

A mixture of 2,5-dihydroxybenzaldehyde (0.138 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in 50 ml methanol was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, single crystals of the title compound, suitable for X-ray diffraction, were formed.

Structure description top

In the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

For the biological properties of hydrazone compounds, see: Patil et al. (2010); Cukurovali et al. (2006). For the crystal structures of hydrazones, see: Mohd Lair et al. (2009); Lin & Sang (2009); Suleiman Gwaram et al. (2010). For hydrazone compounds recently reported by us, see: Han & Zhao (2010a,b). For bond-length data, see: Allen et al. (1987). For similar compounds, see: Li & Ban (2009); Lo & Ng (2009); Ning & Xu (2009); Zhu et al. (2009).

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 compounds with atom labels and 30% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. The molecular packing of the title compound as viewed down b. Hydrogen bonds are shown as dashed lines.

N'-(2,5-Dihydroxybenzylidene)-2-hydroxy-3-methylbenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₄	F(000) = 600
M_r = 286.28	D_x = 1.424 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.333 (2) Å	Cell parameters from 1316 reflections
b = 7.316 (1) Å	θ = 2.7–24.5°
c = 13.738 (2) Å	µ = 0.11 mm⁻¹
β = 94.742 (2)°	T = 298 K
V = 1335.5 (3) Å³	Block, colorless
Z = 4	0.25 × 0.23 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3002 independent reflections
Radiation source: fine-focus sealed tube	1457 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→16
T_min = 0.974, T_max = 0.977	k = −9→9
7636 measured reflections	l = −11→17

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	w = 1/[σ²(F_o²) + (0.0615P)²] where P = (F_o² + 2F_c²)/3
3002 reflections	(Δ/σ)_max = 0.001
197 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄	V = 1335.5 (3) Å³
M_r = 286.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.333 (2) Å	µ = 0.11 mm⁻¹
b = 7.316 (1) Å	T = 298 K
c = 13.738 (2) Å	0.25 × 0.23 × 0.22 mm
β = 94.742 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3002 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1457 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.977	R_int = 0.087
7636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	Δρ_max = 0.22 e Å⁻³
3002 reflections	Δρ_min = −0.26 e Å⁻³
197 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
O1	0.25674 (12)	0.4205 (2)	0.31421 (10)	0.0660 (5)
H1	0.2036	0.3785	0.2893	0.099*
O2	0.12591 (10)	0.3298 (2)	0.17731 (10)	0.0530 (4)
O3	−0.10549 (10)	0.1488 (2)	0.03610 (9)	0.0528 (4)
H3	−0.0498	0.1958	0.0467	0.079*
O4	−0.22237 (11)	0.1219 (2)	−0.35891 (9)	0.0555 (4)
H4	−0.1937	0.2007	−0.3888	0.083*
N1	0.15386 (12)	0.3685 (2)	0.01891 (11)	0.0451 (4)
H1A	0.1913 (15)	0.405 (3)	−0.0290 (12)	0.080*
N2	0.06052 (11)	0.2950 (2)	−0.00814 (11)	0.0441 (4)
C1	0.28436 (13)	0.4534 (3)	0.14397 (13)	0.0401 (5)
C2	0.31477 (14)	0.4737 (3)	0.24325 (14)	0.0447 (5)
C3	0.40822 (15)	0.5532 (3)	0.27436 (15)	0.0513 (6)
C4	0.46896 (16)	0.6081 (3)	0.20408 (17)	0.0573 (6)
H4A	0.5310	0.6606	0.2235	0.069*
C5	0.44147 (15)	0.5884 (3)	0.10597 (16)	0.0570 (6)
H5	0.4846	0.6271	0.0602	0.068*
C6	0.34987 (14)	0.5113 (3)	0.07559 (14)	0.0496 (5)
H6	0.3315	0.4976	0.0092	0.060*
C7	0.43835 (18)	0.5770 (4)	0.38160 (16)	0.0771 (8)
H7A	0.5062	0.6219	0.3903	0.116*
H7B	0.4342	0.4615	0.4142	0.116*
H7C	0.3939	0.6628	0.4088	0.116*
C8	0.18276 (14)	0.3793 (3)	0.11571 (14)	0.0412 (5)
C9	0.03111 (14)	0.2882 (3)	−0.09837 (14)	0.0436 (5)
H9	0.0720	0.3335	−0.1444	0.052*
C10	−0.06605 (13)	0.2097 (3)	−0.12963 (13)	0.0385 (5)
C11	−0.13067 (14)	0.1425 (3)	−0.06259 (13)	0.0404 (5)
C12	−0.22281 (14)	0.0702 (3)	−0.09566 (15)	0.0470 (5)
H12	−0.2653	0.0246	−0.0511	0.056*
C13	−0.25242 (14)	0.0648 (3)	−0.19390 (14)	0.0462 (5)
H13	−0.3150	0.0168	−0.2152	0.055*
C14	−0.18970 (14)	0.1304 (3)	−0.26101 (13)	0.0413 (5)
C15	−0.09706 (13)	0.2005 (3)	−0.22897 (13)	0.0418 (5)
H15	−0.0544	0.2425	−0.2743	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0648 (10)	0.0952 (13)	0.0377 (8)	−0.0074 (9)	0.0018 (7)	0.0016 (8)
O2	0.0484 (8)	0.0677 (10)	0.0431 (8)	−0.0063 (7)	0.0044 (7)	0.0013 (7)
O3	0.0568 (9)	0.0703 (10)	0.0313 (8)	−0.0052 (8)	0.0034 (6)	0.0003 (7)
O4	0.0528 (9)	0.0748 (12)	0.0365 (8)	−0.0068 (7)	−0.0098 (7)	−0.0039 (7)
N1	0.0382 (9)	0.0598 (12)	0.0362 (10)	−0.0042 (8)	−0.0040 (7)	−0.0021 (8)
N2	0.0398 (9)	0.0505 (11)	0.0403 (10)	−0.0002 (7)	−0.0068 (7)	−0.0037 (8)
C1	0.0392 (10)	0.0443 (12)	0.0356 (11)	0.0047 (9)	−0.0037 (9)	−0.0008 (9)
C2	0.0458 (11)	0.0502 (13)	0.0375 (11)	0.0054 (10)	−0.0001 (9)	0.0005 (9)
C3	0.0493 (12)	0.0555 (14)	0.0463 (13)	0.0090 (10)	−0.0138 (10)	−0.0075 (11)
C4	0.0376 (11)	0.0633 (16)	0.0685 (16)	0.0023 (10)	−0.0098 (11)	−0.0054 (12)
C5	0.0404 (12)	0.0762 (16)	0.0538 (14)	−0.0035 (11)	0.0004 (10)	0.0049 (12)
C6	0.0447 (11)	0.0667 (15)	0.0364 (11)	0.0021 (11)	−0.0031 (9)	−0.0001 (10)
C7	0.0754 (16)	0.098 (2)	0.0525 (15)	0.0085 (14)	−0.0247 (13)	−0.0169 (14)
C8	0.0413 (11)	0.0435 (12)	0.0378 (11)	0.0035 (9)	−0.0024 (9)	−0.0022 (9)
C9	0.0392 (11)	0.0523 (13)	0.0389 (12)	0.0015 (9)	0.0011 (9)	−0.0034 (10)
C10	0.0371 (10)	0.0439 (12)	0.0342 (11)	0.0028 (9)	0.0005 (8)	−0.0039 (9)
C11	0.0456 (11)	0.0445 (12)	0.0305 (11)	0.0037 (9)	−0.0006 (9)	−0.0016 (9)
C12	0.0446 (11)	0.0514 (13)	0.0456 (12)	−0.0002 (9)	0.0082 (10)	0.0012 (10)
C13	0.0354 (10)	0.0516 (13)	0.0505 (13)	−0.0042 (9)	−0.0023 (9)	−0.0051 (10)
C14	0.0399 (11)	0.0492 (12)	0.0337 (11)	0.0042 (9)	−0.0039 (9)	−0.0035 (9)
C15	0.0381 (11)	0.0549 (13)	0.0323 (11)	0.0000 (9)	0.0024 (8)	−0.0023 (9)

Geometric parameters (Å, º) top

O1—C2	1.351 (2)	C4—H4A	0.9300
O1—H1	0.8200	C5—C6	1.378 (3)
O2—C8	1.236 (2)	C5—H5	0.9300
O3—C11	1.370 (2)	C6—H6	0.9300
O3—H3	0.8200	C7—H7A	0.9600
O4—C14	1.380 (2)	C7—H7B	0.9600
O4—H4	0.8200	C7—H7C	0.9600
N1—C8	1.356 (2)	C9—C10	1.449 (3)
N1—N2	1.378 (2)	C9—H9	0.9300
N1—H1A	0.899 (19)	C10—C15	1.395 (2)
N2—C9	1.270 (2)	C10—C11	1.401 (3)
C1—C2	1.398 (2)	C11—C12	1.379 (3)
C1—C6	1.400 (3)	C12—C13	1.375 (3)
C1—C8	1.481 (3)	C12—H12	0.9300
C2—C3	1.409 (3)	C13—C14	1.381 (3)
C3—C4	1.371 (3)	C13—H13	0.9300
C3—C7	1.505 (3)	C14—C15	1.376 (2)
C4—C5	1.375 (3)	C15—H15	0.9300

C2—O1—H1	109.5	C3—C7—H7C	109.5
C11—O3—H3	109.5	H7A—C7—H7C	109.5
C14—O4—H4	109.5	H7B—C7—H7C	109.5
C8—N1—N2	117.67 (16)	O2—C8—N1	120.92 (18)
C8—N1—H1A	124.8 (15)	O2—C8—C1	121.82 (17)
N2—N1—H1A	117.5 (15)	N1—C8—C1	117.26 (18)
C9—N2—N1	118.55 (16)	N2—C9—C10	120.09 (18)
C2—C1—C6	118.40 (17)	N2—C9—H9	120.0
C2—C1—C8	118.67 (18)	C10—C9—H9	120.0
C6—C1—C8	122.87 (17)	C15—C10—C11	118.53 (17)
O1—C2—C1	122.42 (18)	C15—C10—C9	119.64 (18)
O1—C2—C3	116.41 (18)	C11—C10—C9	121.83 (17)
C1—C2—C3	121.17 (19)	O3—C11—C12	118.53 (18)
C4—C3—C2	117.80 (18)	O3—C11—C10	121.64 (17)
C4—C3—C7	122.02 (19)	C12—C11—C10	119.82 (17)
C2—C3—C7	120.2 (2)	C13—C12—C11	120.65 (19)
C3—C4—C5	122.33 (19)	C13—C12—H12	119.7
C3—C4—H4A	118.8	C11—C12—H12	119.7
C5—C4—H4A	118.8	C12—C13—C14	120.31 (17)
C4—C5—C6	119.8 (2)	C12—C13—H13	119.8
C4—C5—H5	120.1	C14—C13—H13	119.8
C6—C5—H5	120.1	C15—C14—O4	122.08 (18)
C5—C6—C1	120.46 (19)	C15—C14—C13	119.55 (17)
C5—C6—H6	119.8	O4—C14—C13	118.36 (16)
C1—C6—H6	119.8	C14—C15—C10	121.11 (18)
C3—C7—H7A	109.5	C14—C15—H15	119.4
C3—C7—H7B	109.5	C10—C15—H15	119.4
H7A—C7—H7B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.82	2.5452 (19)	147
O3—H3···N2	0.82	1.85	2.576 (2)	146
O4—H4···O3ⁱ	0.82	1.97	2.774 (2)	169
N1—H1A···O4ⁱⁱ	0.90 (2)	2.27 (2)	3.072 (2)	148 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄
M_r	286.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.333 (2), 7.316 (1), 13.738 (2)
β (°)	94.742 (2)
V (Å³)	1335.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.23 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.974, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	7636, 3002, 1457
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.136, 0.82
No. of reflections	3002
No. of parameters	197
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)	0.22, −0.26

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···O2	0.82	1.82	2.5452 (19)	147.0
O3—H3···N2	0.82	1.85	2.576 (2)	146.0
O4—H4···O3ⁱ	0.82	1.97	2.774 (2)	168.6
N1—H1A···O4ⁱⁱ	0.899 (19)	2.272 (15)	3.072 (2)	148 (2)

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

Acknowledgements

This work was supported by the Applied Chemistry Key Subject of Anhui Province (No. 200802187 C).

References

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