(E)-N′-(2,5-Dimethoxy­benzyl­idene)-2,4-dihydroxy­benzohydrazide

Wei, J.-Y.; Song, D.-G.; Wang, D.-C.; Deng, X.-M.; Liu, J.-X.; Liu, B.

doi:10.1107/S160053681001130X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o996

doi:10.1107/S160053681001130X

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(E)-N′-(2,5-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide

Jing-Yuan Wei,^a De-Guang Song,^a Da-Cheng Wang,^a Xu-Ming Deng,^a Ju-Xiong Liu ^a ^* and Bo Liu ^a ^*

^aCollege of Animal Science and Veterinary Medicine, Jilin University, Changchun 130062, People's Republic of China
^*Correspondence e-mail: jlljx@163.com, jlliubo@yeah.net

(Received 24 March 2010; accepted 25 March 2010; online 31 March 2010)

In the title compound, C₁₆H₁₆N₂O₅, the dihedral angle between the two benzene rings is 4.2 (2)° and an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked into layers lying parallel to the bc plane by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Bhandari et al. (2008 ); Sinha et al. (2008 ). For Schiff base compounds containing 2,5-dimethoxybenzaldehyde, see: Wang et al. (2009 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₅
M_r = 316.31
Monoclinic, P 2₁ /c
a = 7.8600 (16) Å
b = 15.358 (3) Å
c = 12.425 (3) Å
β = 99.80 (3)°
V = 1478.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.984
7757 measured reflections
2626 independent reflections
1698 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.112
S = 1.02
2626 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.82	1.76	2.495 (2)	148
O2—H2⋯O3ⁱ	0.82	1.92	2.664 (2)	151
N1—H1A⋯O1ⁱⁱ	0.86	2.17	3.012 (2)	166
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001130X/hb5375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681001130X/hb5375Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been of great interest for many years. Some of the complexes derived from Schiff bases have been found to have pharmacological and antitumor properties (Bhandari et al., 2008; Sinha et al., 2008). In this paper, the crystal structure of the title compound, (I), a new Schiff base compound derived from the condensation reaction of 2,4-dihydroxybenzohydrazide with 2,5-dimethoxybenzaldehyde is reported.

The Schiff base molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds(Fig. 1). All the bond lengths are within their normal ranges (Allen et al., 1987) and comparable to other Schiff base compounds containing 2,5-dimethoxybenzaldehyde (Wang et al., 2009). The dihedral angle between the two benzene rings is 4.2 (2)°. Intramolecular O—H···O hydrogen bonds are observed(Table 1). Molecules are linked into layers parallel to the bc plane by O—H···O and N—H···O hydrogen bonds(Fig. 2).

Related literature top

For the biological properties of Schiff base compounds, see: Bhandari et al., 2008; Sinha et al., 2008. For Schiff base compounds containing 2,5-dimethoxybenzaldehyde, see: Wang et al., (2009). For reference structural data, see: Allen et al. (1987).

Experimental top

2,5-dimethoxybenzaldehyde (0.1 mmol, 16.6 mg) and 2,4-dihydroxybenzohydrazide (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 colorless solution. Light yellow blocks of (I) were formed by gradual evaporation of the solvent over a period of three days at room temperature.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 30% probability level. The dashed lines indicate hydrogen bonds.
	Fig. 2. The molecular packing of (I). Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity.

(E)-N'-(2,5-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₅	F(000) = 664
M_r = 316.31	D_x = 1.421 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1224 reflections
a = 7.8600 (16) Å	θ = 2.7–22.4°
b = 15.358 (3) Å	µ = 0.11 mm⁻¹
c = 12.425 (3) Å	T = 295 K
β = 99.80 (3)°	Block, light yellow
V = 1478.0 (5) Å³	0.18 × 0.17 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2626 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.981, T_max = 0.984	k = −17→18
7757 measured reflections	l = −13→14

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) = 0.112	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0464P)² + 0.2321P] where P = (F_o² + 2F_c²)/3
2626 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₅	V = 1478.0 (5) Å³
M_r = 316.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8600 (16) Å	µ = 0.11 mm⁻¹
b = 15.358 (3) Å	T = 295 K
c = 12.425 (3) Å	0.18 × 0.17 × 0.15 mm
β = 99.80 (3)°

Data collection top

Bruker SMART CCD diffractometer	2626 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1698 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.039
7757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
2626 reflections	Δρ_min = −0.20 e Å⁻³
212 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	0.5668 (2)	0.18995 (10)	0.34476 (11)	0.0523 (5)
H1	0.6007	0.2404	0.3438	0.078*
O2	0.2931 (2)	−0.02763 (10)	0.10807 (13)	0.0623 (5)
H2	0.3162	−0.0573	0.1635	0.093*
O3	0.6343 (2)	0.33256 (9)	0.26549 (11)	0.0477 (4)
O4	0.7730 (2)	0.58885 (10)	−0.13674 (12)	0.0569 (5)
O5	1.0792 (2)	0.67891 (10)	0.28127 (12)	0.0529 (4)
N1	0.6247 (2)	0.35121 (10)	0.08522 (13)	0.0390 (5)
H1A	0.5957	0.3331	0.0192	0.047*
N2	0.7069 (2)	0.42982 (11)	0.10809 (13)	0.0390 (5)
C1	0.5091 (3)	0.21858 (13)	0.15178 (15)	0.0329 (5)
C2	0.5058 (3)	0.16342 (13)	0.24143 (16)	0.0354 (5)
C3	0.4396 (3)	0.08035 (14)	0.22852 (16)	0.0391 (5)
H3	0.4436	0.0439	0.2887	0.047*
C4	0.3674 (3)	0.05154 (14)	0.12604 (17)	0.0421 (6)
C5	0.3657 (3)	0.10522 (15)	0.03614 (17)	0.0527 (7)
H5	0.3168	0.0857	−0.0331	0.063*
C6	0.4356 (3)	0.18663 (14)	0.04918 (16)	0.0451 (6)
H6	0.4342	0.2218	−0.0119	0.054*
C7	0.5915 (3)	0.30376 (13)	0.17057 (16)	0.0368 (5)
C8	0.7456 (3)	0.47279 (13)	0.02779 (17)	0.0386 (5)
H8	0.7160	0.4520	−0.0432	0.046*
C9	0.8368 (3)	0.55503 (13)	0.04948 (16)	0.0365 (5)
C10	0.8507 (3)	0.61312 (14)	−0.03424 (16)	0.0405 (5)
C11	0.9361 (3)	0.69144 (14)	−0.01112 (19)	0.0463 (6)
H11	0.9448	0.7304	−0.0672	0.056*
C12	1.0081 (3)	0.71168 (15)	0.09455 (18)	0.0468 (6)
H12	1.0627	0.7651	0.1097	0.056*
C13	1.0003 (3)	0.65342 (14)	0.17882 (17)	0.0405 (5)
C14	0.9151 (3)	0.57596 (14)	0.15574 (17)	0.0380 (5)
H14	0.9094	0.5366	0.2119	0.046*
C15	1.1064 (3)	0.61377 (16)	0.36363 (18)	0.0576 (7)
H15A	0.9970	0.5938	0.3785	0.086*
H15B	1.1726	0.6377	0.4290	0.086*
H15C	1.1680	0.5658	0.3390	0.086*
C16	0.8212 (4)	0.63418 (17)	−0.22690 (18)	0.0649 (8)
H16A	0.7839	0.6936	−0.2260	0.097*
H16B	0.7679	0.6070	−0.2938	0.097*
H16C	0.9445	0.6324	−0.2216	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0799 (12)	0.0477 (11)	0.0280 (8)	−0.0122 (9)	0.0054 (8)	0.0022 (7)
O2	0.0909 (13)	0.0381 (10)	0.0523 (10)	−0.0194 (9)	−0.0042 (10)	0.0057 (8)
O3	0.0727 (11)	0.0384 (9)	0.0312 (8)	−0.0072 (8)	0.0064 (7)	−0.0044 (7)
O4	0.0792 (12)	0.0540 (11)	0.0359 (9)	−0.0129 (9)	0.0045 (8)	0.0054 (7)
O5	0.0636 (11)	0.0464 (10)	0.0445 (9)	−0.0064 (8)	−0.0026 (8)	−0.0036 (8)
N1	0.0569 (12)	0.0289 (10)	0.0321 (10)	−0.0078 (9)	0.0098 (8)	−0.0038 (8)
N2	0.0502 (11)	0.0294 (10)	0.0384 (10)	−0.0049 (8)	0.0101 (9)	−0.0028 (8)
C1	0.0414 (12)	0.0287 (12)	0.0293 (11)	0.0003 (9)	0.0075 (9)	0.0018 (9)
C2	0.0394 (12)	0.0395 (13)	0.0283 (11)	0.0013 (10)	0.0082 (9)	0.0015 (10)
C3	0.0469 (13)	0.0365 (13)	0.0343 (12)	−0.0012 (10)	0.0078 (10)	0.0097 (10)
C4	0.0487 (14)	0.0327 (13)	0.0440 (13)	−0.0046 (10)	0.0058 (11)	0.0039 (10)
C5	0.0797 (18)	0.0412 (14)	0.0332 (13)	−0.0130 (13)	−0.0014 (12)	0.0002 (11)
C6	0.0657 (16)	0.0386 (13)	0.0300 (12)	−0.0073 (11)	0.0052 (11)	0.0064 (10)
C7	0.0451 (13)	0.0342 (12)	0.0315 (12)	0.0049 (10)	0.0080 (10)	0.0016 (10)
C8	0.0487 (14)	0.0341 (13)	0.0333 (12)	−0.0013 (10)	0.0076 (10)	−0.0035 (10)
C9	0.0415 (13)	0.0312 (12)	0.0378 (12)	0.0006 (10)	0.0095 (10)	0.0001 (10)
C10	0.0467 (14)	0.0383 (13)	0.0365 (12)	0.0003 (10)	0.0071 (11)	0.0011 (10)
C11	0.0558 (15)	0.0357 (13)	0.0478 (14)	−0.0033 (11)	0.0099 (12)	0.0075 (10)
C12	0.0521 (15)	0.0331 (13)	0.0550 (15)	−0.0036 (10)	0.0090 (12)	0.0000 (11)
C13	0.0420 (13)	0.0370 (13)	0.0421 (13)	−0.0014 (10)	0.0061 (10)	−0.0039 (10)
C14	0.0429 (13)	0.0329 (12)	0.0393 (12)	0.0012 (10)	0.0098 (10)	0.0036 (9)
C15	0.0654 (17)	0.0599 (17)	0.0439 (14)	−0.0057 (13)	−0.0006 (13)	0.0041 (12)
C16	0.089 (2)	0.0674 (19)	0.0395 (14)	0.0021 (16)	0.0143 (14)	0.0098 (13)

Geometric parameters (Å, º) top

O1—C2	1.355 (2)	C5—C6	1.364 (3)
O1—H1	0.8200	C5—H5	0.9300
O2—C4	1.351 (2)	C6—H6	0.9300
O2—H2	0.8200	C8—C9	1.455 (3)
O3—C7	1.251 (2)	C8—H8	0.9300
O4—C10	1.367 (2)	C9—C10	1.389 (3)
O4—C16	1.424 (3)	C9—C14	1.396 (3)
O5—C13	1.375 (2)	C10—C11	1.384 (3)
O5—C15	1.421 (3)	C11—C12	1.374 (3)
N1—C7	1.348 (2)	C11—H11	0.9300
N1—N2	1.376 (2)	C12—C13	1.387 (3)
N1—H1A	0.8600	C12—H12	0.9300
N2—C8	1.275 (2)	C13—C14	1.371 (3)
C1—C6	1.396 (3)	C14—H14	0.9300
C1—C2	1.403 (3)	C15—H15A	0.9600
C1—C7	1.461 (3)	C15—H15B	0.9600
C2—C3	1.377 (3)	C15—H15C	0.9600
C3—C4	1.376 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.387 (3)	C16—H16C	0.9600

C2—O1—H1	109.5	C9—C8—H8	120.7
C4—O2—H2	109.5	C10—C9—C14	118.8 (2)
C10—O4—C16	117.56 (18)	C10—C9—C8	121.21 (19)
C13—O5—C15	117.08 (17)	C14—C9—C8	119.95 (19)
C7—N1—N2	117.31 (17)	O4—C10—C11	123.68 (19)
C7—N1—H1A	121.3	O4—C10—C9	116.29 (19)
N2—N1—H1A	121.3	C11—C10—C9	120.0 (2)
C8—N2—N1	117.29 (17)	C12—C11—C10	120.1 (2)
C6—C1—C2	116.88 (19)	C12—C11—H11	119.9
C6—C1—C7	124.33 (18)	C10—C11—H11	119.9
C2—C1—C7	118.77 (18)	C11—C12—C13	120.8 (2)
O1—C2—C3	117.07 (18)	C11—C12—H12	119.6
O1—C2—C1	121.30 (19)	C13—C12—H12	119.6
C3—C2—C1	121.64 (19)	C14—C13—O5	124.6 (2)
C4—C3—C2	119.61 (19)	C14—C13—C12	119.0 (2)
C4—C3—H3	120.2	O5—C13—C12	116.4 (2)
C2—C3—H3	120.2	C13—C14—C9	121.2 (2)
O2—C4—C3	122.76 (19)	C13—C14—H14	119.4
O2—C4—C5	117.22 (19)	C9—C14—H14	119.4
C3—C4—C5	120.0 (2)	O5—C15—H15A	109.5
C6—C5—C4	120.1 (2)	O5—C15—H15B	109.5
C6—C5—H5	120.0	H15A—C15—H15B	109.5
C4—C5—H5	120.0	O5—C15—H15C	109.5
C5—C6—C1	121.75 (19)	H15A—C15—H15C	109.5
C5—C6—H6	119.1	H15B—C15—H15C	109.5
C1—C6—H6	119.1	O4—C16—H16A	109.5
O3—C7—N1	119.56 (19)	O4—C16—H16B	109.5
O3—C7—C1	120.54 (18)	H16A—C16—H16B	109.5
N1—C7—C1	119.89 (18)	O4—C16—H16C	109.5
N2—C8—C9	118.67 (19)	H16A—C16—H16C	109.5
N2—C8—H8	120.7	H16B—C16—H16C	109.5

C7—N1—N2—C8	176.80 (19)	N1—N2—C8—C9	−178.34 (17)
C6—C1—C2—O1	−176.99 (19)	N2—C8—C9—C10	−166.4 (2)
C7—C1—C2—O1	4.5 (3)	N2—C8—C9—C14	14.8 (3)
C6—C1—C2—C3	2.6 (3)	C16—O4—C10—C11	17.6 (3)
C7—C1—C2—C3	−175.98 (19)	C16—O4—C10—C9	−163.9 (2)
O1—C2—C3—C4	176.54 (19)	C14—C9—C10—O4	179.36 (18)
C1—C2—C3—C4	−3.0 (3)	C8—C9—C10—O4	0.6 (3)
C2—C3—C4—O2	−176.9 (2)	C14—C9—C10—C11	−2.1 (3)
C2—C3—C4—C5	1.7 (3)	C8—C9—C10—C11	179.09 (19)
O2—C4—C5—C6	178.7 (2)	O4—C10—C11—C12	178.8 (2)
C3—C4—C5—C6	0.0 (4)	C9—C10—C11—C12	0.4 (3)
C4—C5—C6—C1	−0.4 (4)	C10—C11—C12—C13	1.7 (3)
C2—C1—C6—C5	−0.8 (3)	C15—O5—C13—C14	14.2 (3)
C7—C1—C6—C5	177.6 (2)	C15—O5—C13—C12	−166.4 (2)
N2—N1—C7—O3	0.6 (3)	C11—C12—C13—C14	−1.9 (3)
N2—N1—C7—C1	−178.22 (17)	C11—C12—C13—O5	178.70 (19)
C6—C1—C7—O3	170.6 (2)	O5—C13—C14—C9	179.43 (19)
C2—C1—C7—O3	−11.0 (3)	C12—C13—C14—C9	0.0 (3)
C6—C1—C7—N1	−10.6 (3)	C10—C9—C14—C13	1.9 (3)
C2—C1—C7—N1	167.86 (19)	C8—C9—C14—C13	−179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.76	2.495 (2)	148
O2—H2···O3ⁱ	0.82	1.92	2.664 (2)	151
N1—H1A···O1ⁱⁱ	0.86	2.17	3.012 (2)	166

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₅
M_r	316.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.8600 (16), 15.358 (3), 12.425 (3)
β (°)	99.80 (3)
V (Å³)	1478.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.18 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	7757, 2626, 1698
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.112, 1.02
No. of reflections	2626
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.76	2.495 (2)	148
O2—H2···O3ⁱ	0.82	1.92	2.664 (2)	151
N1—H1A···O1ⁱⁱ	0.86	2.17	3.012 (2)	166

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

References

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Volume 66| Part 4| April 2010| Page o996

doi:10.1107/S160053681001130X

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