2,4-Dihydr­oxy-N′-(4-methoxy­benzyl­idene)benzohydrazide

Diao, Y.-P.; Huang, S.-S.; Zhang, J.-K.; Kang, T.-G.

doi:10.1107/S1600536808001104

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o470

doi:10.1107/S1600536808001104

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2,4-Dihydroxy-N′-(4-methoxybenzylidene)benzohydrazide

Yun-Peng Diao,^a Shan-Shan Huang,^a Jian-Kui Zhang ^b and Ting-Guo Kang ^b ^*

^aSchool of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China, and ^bLiaoning University of Traditional Chinese Medicine, Shenyang 110032, People's Republic of China
^*Correspondence e-mail: diaoyiwen@126.com

(Received 21 December 2007; accepted 10 January 2008; online 18 January 2008)

The molecule of the title compound, C₁₅H₁₄N₂O₄, displays a trans configuration with respect to the hydrazide C=N bond. The dihedral angle between the two benzene rings is 15.0 (2)°. In the crystal structure, molecules are linked through intermolecular O—H⋯N and O—H⋯O hydrogen bonds, forming layers parallel to the ab plane; an intramolecular N—H⋯O hydrogen bond is also present.

Related literature

For the biological properties of Schiff base compounds, see: Brückner et al. (2000 ); Harrop et al. (2003 ); Ren et al. (2002 ). For related structures, see: Diao (2007 ); Diao et al. (2007 ); Li et al. (2007 ); Huang et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Orthorhombic, P n a 2₁
a = 12.494 (3) Å
b = 5.196 (1) Å
c = 20.825 (4) Å
V = 1351.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.978, T_max = 0.980
7661 measured reflections
1519 independent reflections
1382 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.079
S = 1.06
1519 reflections
196 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.901 (10)	1.94 (2)	2.646 (2)	134 (3)
O4—H4⋯O2ⁱ	0.82	1.85	2.671 (2)	174
O3—H3⋯N1ⁱⁱ	0.82	2.48	3.234 (2)	154
O3—H3⋯O2ⁱⁱ	0.82	2.14	2.788 (2)	136
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{7\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, z]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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/S1600536808001104/rz2192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001104/rz2192Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have received much attention in recent years. Some Schiff base metal complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on the synthesis and characterization of Schiff base compounds (Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title ligand.

The molecule of the title compound displays a trans configuration with respect to the C=N bond (Fig. 1). The dihedral angle between the two benzene rings is 15.0 (2)°. The molecular conformation is stabilized by an intramolecular N—H···O hydrogen interaction (Table 1). In the crystal, molecules are linked through intermolecular O—H···N and O—H···O hydrogen bonds (Table 1), forming layers parallel to the ab plane (Fig. 2).

Related literature top

For the biological properties of Schiff base compounds, see: Brückner et al. (2000); Harrop et al. (2003); Ren et al. (2002). For related structures, see: Diao (2007); Diao et al. (2007); Li et al. (2007); Huang et al. (2007).

Experimental top

4-Methoxybenzaldehyde (0.1 mmol, 13.6 mg) and 2,4-dihydroxybenzoic acid hydrazide (0.1 mmol, 16.8 mg) were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of three days at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound viewed along the b axis. Intermolecular hydrogen bonds are shown as dashed lines.

2,4-Dihydroxy-N'-(4-methoxybenzylidene)benzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₄	F(000) = 600
M_r = 286.28	D_x = 1.407 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3064 reflections
a = 12.494 (3) Å	θ = 2.7–27.2°
b = 5.196 (1) Å	µ = 0.10 mm⁻¹
c = 20.825 (4) Å	T = 298 K
V = 1351.9 (5) Å³	Block, colourless
Z = 4	0.22 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1519 independent reflections
Radiation source: fine-focus sealed tube	1382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→15
T_min = 0.978, T_max = 0.980	k = −6→5
7661 measured reflections	l = −25→26

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0468P)² + 0.123P] where P = (F_o² + 2F_c²)/3
1519 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.13 e Å⁻³
2 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄	V = 1351.9 (5) Å³
M_r = 286.28	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.494 (3) Å	µ = 0.10 mm⁻¹
b = 5.196 (1) Å	T = 298 K
c = 20.825 (4) Å	0.22 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1519 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1382 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.980	R_int = 0.025
7661 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.13 e Å⁻³
1519 reflections	Δρ_min = −0.15 e Å⁻³
196 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	−0.07270 (13)	0.0953 (3)	0.95352 (10)	0.0550 (5)
O2	0.05579 (11)	1.2801 (3)	0.67387 (9)	0.0461 (4)
O3	0.37031 (11)	1.3774 (3)	0.73708 (8)	0.0411 (4)
H3	0.4359	1.3777	0.7357	0.062*
O4	0.41377 (12)	2.0606 (3)	0.58664 (8)	0.0438 (4)
H4	0.4607	2.1038	0.6120	0.066*
N1	0.11530 (13)	0.9630 (3)	0.76750 (9)	0.0358 (4)
N2	0.18526 (13)	1.1298 (3)	0.73763 (9)	0.0354 (4)
C1	0.09837 (17)	0.6230 (4)	0.84516 (11)	0.0361 (4)
C2	−0.01216 (19)	0.5952 (5)	0.83938 (12)	0.0461 (6)
H2	−0.0499	0.6974	0.8105	0.055*
C3	−0.06553 (18)	0.4174 (5)	0.87614 (13)	0.0490 (6)
H3A	−0.1392	0.3994	0.8717	0.059*
C4	−0.01114 (18)	0.2637 (4)	0.91993 (11)	0.0394 (5)
C5	0.09840 (18)	0.2886 (4)	0.92608 (12)	0.0421 (5)
H5	0.1360	0.1855	0.9548	0.051*
C6	0.15162 (17)	0.4694 (4)	0.88882 (12)	0.0424 (5)
H6	0.2253	0.4876	0.8934	0.051*
C7	0.15821 (17)	0.8097 (4)	0.80745 (11)	0.0377 (5)
H7	0.2320	0.8173	0.8129	0.045*
C8	0.15001 (14)	1.2894 (4)	0.69171 (10)	0.0317 (4)
C9	0.22691 (14)	1.4776 (4)	0.66456 (10)	0.0304 (4)
C10	0.33078 (14)	1.5226 (4)	0.68779 (10)	0.0306 (4)
C11	0.39332 (15)	1.7176 (4)	0.66248 (10)	0.0324 (4)
H11	0.4610	1.7489	0.6793	0.039*
C12	0.35562 (16)	1.8657 (4)	0.61231 (10)	0.0335 (4)
C13	0.25493 (16)	1.8182 (4)	0.58614 (11)	0.0394 (5)
H13	0.2303	1.9129	0.5512	0.047*
C14	0.19282 (16)	1.6282 (4)	0.61303 (10)	0.0373 (5)
H14	0.1250	1.5987	0.5961	0.045*
C15	−0.0203 (2)	−0.0748 (5)	0.99722 (14)	0.0540 (6)
H15A	0.0135	0.0235	1.0306	0.081*
H15B	0.0328	−0.1729	0.9746	0.081*
H15C	−0.0720	−0.1893	1.0159	0.081*
H2A	0.2547 (11)	1.133 (6)	0.7492 (17)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0502 (9)	0.0531 (9)	0.0618 (11)	−0.0010 (8)	0.0024 (9)	0.0263 (8)
O2	0.0247 (7)	0.0480 (8)	0.0657 (11)	−0.0043 (6)	−0.0063 (7)	0.0119 (8)
O3	0.0221 (6)	0.0521 (9)	0.0490 (9)	−0.0013 (6)	−0.0039 (6)	0.0161 (8)
O4	0.0398 (8)	0.0458 (9)	0.0458 (8)	−0.0114 (7)	−0.0038 (7)	0.0110 (7)
N1	0.0311 (8)	0.0368 (9)	0.0395 (9)	−0.0081 (7)	0.0034 (7)	0.0004 (8)
N2	0.0258 (8)	0.0401 (9)	0.0404 (9)	−0.0046 (7)	0.0007 (8)	0.0049 (7)
C1	0.0364 (10)	0.0354 (10)	0.0364 (10)	−0.0019 (8)	−0.0005 (8)	−0.0012 (8)
C2	0.0383 (11)	0.0517 (13)	0.0481 (13)	−0.0061 (10)	−0.0100 (10)	0.0175 (11)
C3	0.0346 (10)	0.0557 (13)	0.0567 (14)	−0.0070 (10)	−0.0084 (11)	0.0186 (11)
C4	0.0422 (12)	0.0360 (10)	0.0399 (11)	−0.0009 (9)	0.0012 (9)	0.0062 (9)
C5	0.0439 (12)	0.0400 (11)	0.0425 (11)	0.0066 (9)	−0.0042 (9)	0.0068 (10)
C6	0.0347 (10)	0.0451 (12)	0.0476 (13)	0.0029 (9)	−0.0033 (10)	0.0006 (10)
C7	0.0311 (10)	0.0418 (11)	0.0404 (11)	−0.0033 (9)	−0.0001 (9)	−0.0023 (9)
C8	0.0239 (9)	0.0318 (9)	0.0394 (10)	0.0013 (7)	0.0020 (8)	−0.0037 (8)
C9	0.0233 (8)	0.0324 (9)	0.0356 (10)	0.0009 (7)	0.0000 (8)	−0.0020 (8)
C10	0.0240 (8)	0.0333 (9)	0.0346 (10)	0.0032 (7)	0.0006 (8)	0.0007 (8)
C11	0.0227 (8)	0.0371 (10)	0.0376 (10)	−0.0001 (7)	−0.0016 (8)	−0.0006 (8)
C12	0.0296 (9)	0.0346 (10)	0.0363 (10)	−0.0020 (8)	0.0024 (8)	−0.0004 (8)
C13	0.0333 (10)	0.0460 (11)	0.0389 (11)	−0.0003 (9)	−0.0065 (9)	0.0089 (10)
C14	0.0262 (9)	0.0437 (11)	0.0419 (11)	−0.0031 (8)	−0.0081 (8)	0.0019 (9)
C15	0.0663 (16)	0.0453 (12)	0.0504 (14)	0.0093 (13)	0.0052 (13)	0.0159 (11)

Geometric parameters (Å, º) top

O1—C4	1.359 (3)	C4—C5	1.381 (3)
O1—C15	1.427 (3)	C5—C6	1.388 (3)
O2—C8	1.235 (2)	C5—H5	0.9300
O3—C10	1.366 (2)	C6—H6	0.9300
O3—H3	0.8200	C7—H7	0.9300
O4—C12	1.356 (2)	C8—C9	1.483 (3)
O4—H4	0.8200	C9—C14	1.394 (3)
N1—C7	1.270 (3)	C9—C10	1.405 (3)
N1—N2	1.379 (2)	C10—C11	1.384 (3)
N2—C8	1.340 (3)	C11—C12	1.380 (3)
N2—H2A	0.901 (10)	C11—H11	0.9300
C1—C6	1.381 (3)	C12—C13	1.393 (3)
C1—C2	1.394 (3)	C13—C14	1.375 (3)
C1—C7	1.455 (3)	C13—H13	0.9300
C2—C3	1.373 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.390 (3)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600

C4—O1—C15	117.86 (19)	O2—C8—N2	120.23 (18)
C10—O3—H3	109.5	O2—C8—C9	121.91 (18)
C12—O4—H4	109.5	N2—C8—C9	117.85 (16)
C7—N1—N2	114.96 (16)	C14—C9—C10	117.00 (17)
C8—N2—N1	120.15 (16)	C14—C9—C8	117.74 (17)
C8—N2—H2A	120 (2)	C10—C9—C8	125.23 (17)
N1—N2—H2A	120 (2)	O3—C10—C11	119.10 (16)
C6—C1—C2	118.3 (2)	O3—C10—C9	120.06 (16)
C6—C1—C7	119.57 (19)	C11—C10—C9	120.82 (17)
C2—C1—C7	122.1 (2)	C12—C11—C10	120.26 (17)
C3—C2—C1	120.2 (2)	C12—C11—H11	119.9
C3—C2—H2	119.9	C10—C11—H11	119.9
C1—C2—H2	119.9	O4—C12—C11	122.14 (18)
C2—C3—C4	121.0 (2)	O4—C12—C13	117.50 (18)
C2—C3—H3A	119.5	C11—C12—C13	120.36 (18)
C4—C3—H3A	119.5	C14—C13—C12	118.52 (19)
O1—C4—C5	125.0 (2)	C14—C13—H13	120.7
O1—C4—C3	115.5 (2)	C12—C13—H13	120.7
C5—C4—C3	119.5 (2)	C13—C14—C9	122.94 (18)
C4—C5—C6	119.1 (2)	C13—C14—H14	118.5
C4—C5—H5	120.4	C9—C14—H14	118.5
C6—C5—H5	120.4	O1—C15—H15A	109.5
C1—C6—C5	121.9 (2)	O1—C15—H15B	109.5
C1—C6—H6	119.0	H15A—C15—H15B	109.5
C5—C6—H6	119.0	O1—C15—H15C	109.5
N1—C7—C1	123.69 (19)	H15A—C15—H15C	109.5
N1—C7—H7	118.2	H15B—C15—H15C	109.5
C1—C7—H7	118.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.90 (1)	1.94 (2)	2.646 (2)	134 (3)
O4—H4···O2ⁱ	0.82	1.85	2.671 (2)	174
O3—H3···N1ⁱⁱ	0.82	2.48	3.234 (2)	154
O3—H3···O2ⁱⁱ	0.82	2.14	2.788 (2)	136

Symmetry codes: (i) x+1/2, −y+7/2, z; (ii) x+1/2, −y+5/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄
M_r	286.28
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	12.494 (3), 5.196 (1), 20.825 (4)
V (Å³)	1351.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.978, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	7661, 1519, 1382
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.079, 1.06
No. of reflections	1519
No. of parameters	196
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.15

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.901 (10)	1.94 (2)	2.646 (2)	134 (3)
O4—H4···O2ⁱ	0.82	1.85	2.671 (2)	174.1
O3—H3···N1ⁱⁱ	0.82	2.48	3.234 (2)	153.5
O3—H3···O2ⁱⁱ	0.82	2.14	2.788 (2)	136.1

Symmetry codes: (i) x+1/2, −y+7/2, z; (ii) x+1/2, −y+5/2, z.

Acknowledgements

This project was supported by a research grant from Dalian Medical University.

References

Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100–6106. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diao, Y.-P. (2007). Acta Cryst. E63, m1453–m1454. Web of Science CSD CrossRef IUCr Journals Google Scholar
Diao, Y.-P., Shu, X.-H., Zhang, B.-J., Zhen, Y.-H. & Kang, T.-G. (2007). Acta Cryst. E63, m1816. CSD CrossRef IUCr Journals Google Scholar
Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411. Web of Science CSD CrossRef Google Scholar
Huang, S.-S., Zhou, Q. & Diao, Y.-P. (2007). Acta Cryst. E63, o4659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, K., Huang, S.-S., Zhang, B.-J., Meng, D.-L. & Diao, Y.-P. (2007). Acta Cryst. E63, m2291. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410–419. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar