4-Hy­droxy-N′-(4-hy­droxy-3-nitro­benzyl­idene)benzohydrazide

Zhang, Z.

doi:10.1107/S1600536811000195

organic compounds

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Volume 67| Part 2| February 2011| Page o300

doi:10.1107/S1600536811000195

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4-Hydroxy-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide

Zhen Zhang ^a ^*

^aExperimental Center, Linyi University, Linyi Shandong 276005, People's Republic of China
^*Correspondence e-mail: zhangzhen_lynu@126.com

(Received 28 December 2010; accepted 4 January 2011; online 8 January 2011)

The molecule of the title compound, C₁₄H₁₁N₃O₅, assumes an E configuration with respect to the methylidene unit. An intramolecular O—H⋯O hydrogen bond is present in the molecule. The dihedral angle between the mean planes of the two benzene rings is 5.46 (15)°. The crystal structure is stabilized by intermolecular O—H⋯O, O—H⋯N, and N—H⋯O hydrogen bonds.

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010 ); Avaji et al. (2009 ); Fan et al. (2010 ); Rasras et al. (2010 ). For similar hydrazone compounds, see: Ahmad et al. (2010 ); Ban (2010 ); Ji & Lu (2010 ); Shalash et al. (2010 ).

Experimental

Crystal data

C₁₄H₁₁N₃O₅
M_r = 301.26
Monoclinic, P 2₁ /n
a = 8.786 (3) Å
b = 14.882 (2) Å
c = 10.3064 (17) Å
β = 91.100 (2)°
V = 1347.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.964, T_max = 0.967
7079 measured reflections
2952 independent reflections
1353 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.137
S = 1.06
2952 reflections
204 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.82	1.93	2.736 (3)	169
O1—H1A⋯N2ⁱ	0.82	2.61	3.121 (3)	122
O3—H3⋯O4	0.82	1.90	2.592 (4)	142
N1—H1⋯O5ⁱⁱ	0.90 (1)	2.32 (1)	3.203 (4)	167 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536811000195/su2243sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000195/su2243Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Ajani et al., 2010; Avaji et al., 2009; Fan et al., 2010; Rasras et al., 2010). As a continuatio of our work on the hydrazone compounds, the new title hydrazone compound was prepared and structurally characterized.

The molecule of the title compound assumes an E configuration with respect to the methylidene unit (Fig. 1). The dihedral angle between the best mean planes of the two benzene rings is 5.46 (15)°. An intramolecular O—H···O hydrogen bond is present in the molecule (Table 1). The bond lengths are comparable to those observed in similar hydrazone compounds (Ahmad et al., 2010; Ban, 2010; Ji & Lu, 2010; Shalash et al., 2010).

The crystal structure is stabilized by intermolecular O—H···O, O—H···N, and N—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the biological applications of hydrazone compounds, see: Ajani et al. (2010); Avaji et al. (2009); Fan et al. (2010); Rasras et al. (2010). For similar hydrazone compounds, see: Ahmad et al. (2010); Ban (2010); Ji & Lu (2010); Shalash et al. (2010).

Experimental top

An ethanol solution (50 ml) of 4-hydroxybenzohydrazide (0.01 mol) and 4-hydroxy-3-nitrobenzaldehyde (0.01 mol) was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals, suitable for X-ray diffraction, were formed by slow evaporation of the solution in air.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. A view of the molecular structure of the title compound, showing the displacement ellipsoids at the 30% probability level. The intramolecular O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. A perspective view along the a-axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines. H-atoms not involved in hydrogen bonding have been omitted for clarity.

4-Hydroxy-N'-(4-hydroxy-3-nitrobenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₁N₃O₅	F(000) = 624
M_r = 301.26	D_x = 1.485 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.786 (3) Å	Cell parameters from 1674 reflections
b = 14.882 (2) Å	θ = 2.4–26.9°
c = 10.3064 (17) Å	µ = 0.12 mm⁻¹
β = 91.100 (2)°	T = 298 K
V = 1347.3 (5) Å³	Block, yellow
Z = 4	0.32 × 0.30 × 0.29 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2952 independent reflections
Radiation source: fine-focus sealed tube	1353 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→11
T_min = 0.964, T_max = 0.967	k = −19→19
7079 measured reflections	l = −13→7

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0262P)² + 0.9404P] where P = (F_o² + 2F_c²)/3
2952 reflections	(Δ/σ)_max < 0.001
204 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₄H₁₁N₃O₅	V = 1347.3 (5) Å³
M_r = 301.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.786 (3) Å	µ = 0.12 mm⁻¹
b = 14.882 (2) Å	T = 298 K
c = 10.3064 (17) Å	0.32 × 0.30 × 0.29 mm
β = 91.100 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2952 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1353 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.967	R_int = 0.050
7079 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.21 e Å⁻³
2952 reflections	Δρ_min = −0.21 e Å⁻³
204 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
N1	0.4602 (3)	0.40859 (16)	0.1386 (3)	0.0442 (7)
N2	0.3606 (3)	0.34194 (16)	0.0989 (3)	0.0419 (7)
O1	1.0054 (2)	0.64891 (13)	0.3680 (3)	0.0577 (7)
H1A	0.9704	0.6998	0.3614	0.087*
O2	0.6482 (2)	0.30744 (13)	0.1654 (2)	0.0521 (7)
O3	−0.2256 (3)	0.12672 (15)	−0.0998 (3)	0.0675 (8)
H3	−0.3047	0.1529	−0.1200	0.101*
O4	−0.3830 (3)	0.26935 (19)	−0.1553 (3)	0.0766 (9)
O5	−0.2875 (3)	0.40196 (19)	−0.1256 (3)	0.0801 (9)
C1	0.7049 (3)	0.45812 (18)	0.2226 (3)	0.0344 (7)
C2	0.6644 (3)	0.54841 (18)	0.2232 (3)	0.0411 (8)
H2	0.5691	0.5655	0.1909	0.049*
C3	0.7623 (3)	0.61274 (19)	0.2707 (3)	0.0432 (8)
H3A	0.7332	0.6728	0.2699	0.052*
C4	0.9033 (3)	0.58892 (19)	0.3194 (3)	0.0398 (8)
C5	0.9456 (4)	0.49917 (19)	0.3202 (3)	0.0503 (10)
H5	1.0406	0.4824	0.3534	0.060*
C6	0.8471 (3)	0.4349 (2)	0.2720 (3)	0.0503 (10)
H6	0.8766	0.3749	0.2726	0.060*
C7	0.6036 (3)	0.38575 (19)	0.1743 (3)	0.0382 (8)
C8	0.2280 (4)	0.3678 (2)	0.0654 (3)	0.0444 (9)
H8	0.2047	0.4287	0.0685	0.053*
C9	0.1110 (3)	0.3044 (2)	0.0222 (3)	0.0398 (8)
C10	−0.0244 (3)	0.3372 (2)	−0.0261 (3)	0.0428 (8)
H10	−0.0398	0.3989	−0.0301	0.051*
C11	−0.1385 (3)	0.2798 (2)	−0.0692 (3)	0.0410 (8)
C12	−0.1193 (4)	0.1874 (2)	−0.0631 (3)	0.0455 (9)
C13	0.0193 (4)	0.1544 (2)	−0.0147 (3)	0.0486 (9)
H13	0.0347	0.0926	−0.0102	0.058*
C14	0.1324 (4)	0.2110 (2)	0.0262 (3)	0.0446 (9)
H14	0.2243	0.1875	0.0569	0.053*
N3	−0.2779 (3)	0.3202 (2)	−0.1195 (3)	0.0561 (8)
H1	0.424 (3)	0.4649 (10)	0.144 (3)	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0310 (16)	0.0268 (13)	0.075 (2)	0.0000 (12)	−0.0032 (14)	−0.0041 (14)
N2	0.0364 (17)	0.0336 (14)	0.0558 (19)	−0.0036 (12)	0.0034 (14)	−0.0015 (13)
O1	0.0463 (15)	0.0301 (12)	0.0962 (19)	−0.0006 (11)	−0.0149 (14)	−0.0028 (13)
O2	0.0450 (14)	0.0267 (11)	0.0845 (18)	0.0024 (10)	−0.0015 (12)	−0.0041 (12)
O3	0.0593 (17)	0.0626 (16)	0.081 (2)	−0.0226 (13)	−0.0018 (15)	−0.0094 (15)
O4	0.0474 (17)	0.094 (2)	0.088 (2)	−0.0095 (16)	−0.0138 (15)	−0.0119 (17)
O5	0.0598 (18)	0.0628 (18)	0.117 (2)	0.0151 (15)	−0.0165 (16)	0.0017 (17)
C1	0.0307 (18)	0.0281 (15)	0.045 (2)	−0.0001 (13)	0.0075 (15)	0.0008 (14)
C2	0.033 (2)	0.0310 (17)	0.060 (2)	0.0037 (14)	0.0008 (17)	0.0031 (15)
C3	0.040 (2)	0.0259 (16)	0.064 (2)	0.0021 (14)	0.0000 (17)	0.0058 (16)
C4	0.0373 (19)	0.0296 (16)	0.052 (2)	−0.0024 (14)	0.0029 (17)	−0.0002 (15)
C5	0.036 (2)	0.0318 (17)	0.082 (3)	0.0063 (16)	−0.0109 (19)	−0.0018 (18)
C6	0.043 (2)	0.0273 (17)	0.080 (3)	0.0083 (15)	−0.004 (2)	−0.0029 (17)
C7	0.037 (2)	0.0315 (17)	0.046 (2)	0.0021 (14)	0.0081 (16)	0.0033 (15)
C8	0.041 (2)	0.0315 (17)	0.061 (2)	0.0032 (15)	0.0027 (18)	0.0009 (16)
C9	0.0335 (19)	0.0374 (17)	0.049 (2)	−0.0010 (14)	0.0075 (16)	0.0014 (16)
C10	0.037 (2)	0.0374 (18)	0.054 (2)	0.0014 (15)	0.0057 (17)	−0.0008 (16)
C11	0.034 (2)	0.048 (2)	0.042 (2)	0.0007 (15)	0.0065 (16)	−0.0042 (16)
C12	0.044 (2)	0.050 (2)	0.042 (2)	−0.0134 (17)	0.0061 (17)	−0.0068 (17)
C13	0.055 (2)	0.0335 (17)	0.057 (2)	−0.0027 (17)	0.0083 (19)	−0.0020 (17)
C14	0.041 (2)	0.0375 (19)	0.056 (2)	−0.0010 (15)	0.0033 (17)	0.0012 (16)
N3	0.0403 (19)	0.071 (2)	0.057 (2)	0.0008 (17)	0.0035 (16)	−0.0043 (17)

Geometric parameters (Å, º) top

N1—C7	1.349 (4)	C3—H3A	0.9300
N1—N2	1.380 (3)	C4—C5	1.387 (4)
N1—H1	0.899 (10)	C5—C6	1.376 (4)
N2—C8	1.269 (4)	C5—H5	0.9300
O1—C4	1.355 (3)	C6—H6	0.9300
O1—H1A	0.8200	C8—C9	1.458 (4)
O2—C7	1.234 (3)	C8—H8	0.9300
O3—C12	1.347 (4)	C9—C10	1.371 (4)
O3—H3	0.8200	C9—C14	1.403 (4)
O4—N3	1.244 (3)	C10—C11	1.383 (4)
O5—N3	1.222 (4)	C10—H10	0.9300
C1—C6	1.383 (4)	C11—C12	1.387 (4)
C1—C2	1.390 (4)	C11—N3	1.451 (4)
C1—C7	1.478 (4)	C12—C13	1.396 (4)
C2—C3	1.371 (4)	C13—C14	1.363 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.374 (4)	C14—H14	0.9300

C7—N1—N2	118.9 (2)	N1—C7—C1	117.5 (3)
C7—N1—H1	123 (2)	N2—C8—C9	121.7 (3)
N2—N1—H1	118 (2)	N2—C8—H8	119.2
C8—N2—N1	115.9 (2)	C9—C8—H8	119.2
C4—O1—H1A	109.5	C10—C9—C14	118.5 (3)
C12—O3—H3	109.5	C10—C9—C8	118.9 (3)
C6—C1—C2	118.0 (3)	C14—C9—C8	122.6 (3)
C6—C1—C7	118.4 (3)	C9—C10—C11	121.0 (3)
C2—C1—C7	123.6 (3)	C9—C10—H10	119.5
C3—C2—C1	121.1 (3)	C11—C10—H10	119.5
C3—C2—H2	119.4	C10—C11—C12	120.8 (3)
C1—C2—H2	119.4	C10—C11—N3	117.4 (3)
C2—C3—C4	120.4 (3)	C12—C11—N3	121.9 (3)
C2—C3—H3A	119.8	O3—C12—C11	124.7 (3)
C4—C3—H3A	119.8	O3—C12—C13	117.3 (3)
O1—C4—C3	123.4 (3)	C11—C12—C13	118.0 (3)
O1—C4—C5	117.2 (3)	C14—C13—C12	121.2 (3)
C3—C4—C5	119.4 (3)	C14—C13—H13	119.4
C6—C5—C4	120.0 (3)	C12—C13—H13	119.4
C6—C5—H5	120.0	C13—C14—C9	120.5 (3)
C4—C5—H5	120.0	C13—C14—H14	119.8
C5—C6—C1	121.1 (3)	C9—C14—H14	119.8
C5—C6—H6	119.4	O5—N3—O4	122.7 (3)
C1—C6—H6	119.4	O5—N3—C11	119.2 (3)
O2—C7—N1	120.9 (3)	O4—N3—C11	118.1 (3)
O2—C7—C1	121.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	1.93	2.736 (3)	169
O1—H1A···N2ⁱ	0.82	2.61	3.121 (3)	122
O3—H3···O4	0.82	1.90	2.592 (4)	142
N1—H1···O5ⁱⁱ	0.90 (1)	2.32 (1)	3.203 (4)	167 (3)

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₅
M_r	301.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.786 (3), 14.882 (2), 10.3064 (17)
β (°)	91.100 (2)
V (Å³)	1347.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.32 × 0.30 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.964, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	7079, 2952, 1353
R_int	0.050

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.137, 1.06
No. of reflections	2952
No. of parameters	204
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)	0.21, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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—H1A···O2ⁱ	0.82	1.93	2.736 (3)	169
O1—H1A···N2ⁱ	0.82	2.61	3.121 (3)	122
O3—H3···O4	0.82	1.90	2.592 (4)	142
N1—H1···O5ⁱⁱ	0.899 (10)	2.321 (13)	3.203 (4)	167 (3)

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x, −y+1, −z.

Acknowledgements

The author thanks the Experimental Center of Linyi University for supporting this work.

References

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