(E)-4-Chloro-N′-(5-hydr­oxy-2-nitro­benzyl­idene)benzohydrazide

Cao, G.-B.

doi:10.1107/S1600536809035740

organic compounds

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Volume 65| Part 10| October 2009| Page o2415

doi:10.1107/S1600536809035740

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(E)-4-Chloro-N′-(5-hydroxy-2-nitrobenzylidene)benzohydrazide

Guo-Biao Cao ^a ^*

^aDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
^*Correspondence e-mail: guobiao_cao@126.com

(Received 24 August 2009; accepted 4 September 2009; online 9 September 2009)

The title compound, C₁₄H₁₀ClN₃O₄, was synthesized by the reaction of 5-hydroxy-2-nitrobenzaldehyde with an equimolar quantity of 4-chlorobenzohydrazide in methanol. The molecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 3.9 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ); Fun et al. (2008 ); Li & Ban (2009 ); Zhu et al. (2009 ); Yang (2007 ); You et al. (2008 ). For the hydrazone compounds previously reported by our group, see: Qu et al. (2008 ); Yang et al. (2008 ), Cao & Lu (2009a ,b ), Cao (2009a ,b ).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₄
M_r = 319.70
Triclinic, $[P \overline 1]$
a = 7.5386 (2) Å
b = 8.1677 (2) Å
c = 12.3435 (4) Å
α = 90.820 (3)°
β = 106.056 (2)°
γ = 109.014 (2)°
V = 685.95 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.934, T_max = 0.942
4267 measured reflections
2933 independent reflections
2444 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.04
2933 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.82	1.89	2.7093 (17)	174
N2—H2⋯O1ⁱⁱ	0.896 (10)	2.290 (11)	3.1649 (18)	165 (2)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+1, -z+1.

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/S1600536809035740/om2273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035740/om2273Isup2.hkl

checkCIF report

Comment top

In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b), the title new hydrazone compound, derived from the reaction of 5-hydroxy-2-nitrobenzaldehyde with an equimolar quantity of 4-chlorobenzohydrazide, is reported.

In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 3.9 (2)°. The molecule displays an E configuration about the C═N bond. 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 b axis, Fig. 2.

Related literature top

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Fun et al. (2008); Li & Ban (2009); Zhu et al. (2009); Yang (2007); You et al. (2008). For the hydrazone compounds previously reported by our group, see: Qu et al. (2008); Yang et al. (2008), Cao & Lu (2009a,b), Cao (2009a,b).

Experimental top

The compound was prepared by refluxing equimolar quantities of 5-hydroxy-2-nitrobenzaldehyde with 4-chlorobenzohydrazide in methanol. Colorless block-like crystals were formed by slow evaporation of the solution in air.

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 with ellipsoids drawn at the 30% probability level.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

(E)-4-Chloro-N'-(5-hydroxy-2-nitrobenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₀ClN₃O₄	Z = 2
M_r = 319.70	F(000) = 328
Triclinic, P1	D_x = 1.548 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5386 (2) Å	Cell parameters from 2079 reflections
b = 8.1677 (2) Å	θ = 2.6–30.1°
c = 12.3435 (4) Å	µ = 0.30 mm⁻¹
α = 90.820 (3)°	T = 298 K
β = 106.056 (2)°	Block, colorless
γ = 109.014 (2)°	0.23 × 0.20 × 0.20 mm
V = 685.95 (4) Å³

Data collection top

Bruker SMART 1K diffractometer	2933 independent reflections
Radiation source: fine-focus sealed tube	2444 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.934, T_max = 0.942	k = −10→10
4267 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.051P)² + 0.2581P] where P = (F_o² + 2F_c²)/3
2933 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₄H₁₀ClN₃O₄	γ = 109.014 (2)°
M_r = 319.70	V = 685.95 (4) Å³
Triclinic, P1	Z = 2
a = 7.5386 (2) Å	Mo Kα radiation
b = 8.1677 (2) Å	µ = 0.30 mm⁻¹
c = 12.3435 (4) Å	T = 298 K
α = 90.820 (3)°	0.23 × 0.20 × 0.20 mm
β = 106.056 (2)°

Data collection top

Bruker SMART 1K diffractometer	2933 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2444 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.942	R_int = 0.013
4267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
2933 reflections	Δρ_min = −0.37 e Å⁻³
203 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 > 2sigma(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
Cl1	1.99310 (8)	1.22131 (10)	1.02766 (6)	0.0873 (3)
N1	0.89654 (18)	0.85347 (17)	0.58743 (11)	0.0363 (3)
N2	1.08279 (18)	0.88906 (18)	0.65933 (12)	0.0365 (3)
N3	0.6482 (2)	0.46355 (18)	0.30087 (13)	0.0424 (3)
O1	0.7870 (2)	0.43682 (18)	0.36768 (12)	0.0570 (4)
O2	0.5932 (3)	0.4105 (2)	0.20048 (13)	0.0756 (5)
O3	0.22232 (17)	0.82467 (17)	0.43739 (11)	0.0489 (3)
H3	0.1313	0.8286	0.3839	0.073*
O4	1.08646 (17)	1.14913 (16)	0.72801 (11)	0.0458 (3)
C1	0.6246 (2)	0.67228 (19)	0.44254 (13)	0.0299 (3)
C2	0.5411 (2)	0.55749 (19)	0.34209 (13)	0.0332 (3)
C3	0.3510 (2)	0.5302 (2)	0.27424 (14)	0.0407 (4)
H3A	0.2995	0.4535	0.2079	0.049*
C4	0.2379 (2)	0.6149 (2)	0.30395 (15)	0.0407 (4)
H4	0.1098	0.5944	0.2590	0.049*
C5	0.3180 (2)	0.7317 (2)	0.40214 (14)	0.0352 (3)
C6	0.5077 (2)	0.75750 (19)	0.46992 (13)	0.0322 (3)
H6	0.5584	0.8346	0.5361	0.039*
C7	0.8272 (2)	0.7162 (2)	0.51835 (13)	0.0326 (3)
H7	0.9012	0.6456	0.5154	0.039*
C8	1.1687 (2)	1.0418 (2)	0.72753 (13)	0.0337 (3)
C9	1.3720 (2)	1.0754 (2)	0.80277 (13)	0.0335 (3)
C10	1.4371 (3)	1.1911 (2)	0.90032 (14)	0.0438 (4)
H10	1.3523	1.2403	0.9185	0.053*
C11	1.6278 (3)	1.2339 (3)	0.97075 (15)	0.0511 (5)
H11	1.6716	1.3107	1.0366	0.061*
C12	1.7510 (3)	1.1612 (3)	0.94169 (15)	0.0474 (4)
C13	1.6913 (2)	1.0459 (2)	0.84568 (15)	0.0437 (4)
H13	1.7774	0.9981	0.8278	0.052*
C14	1.5000 (2)	1.0026 (2)	0.77637 (14)	0.0362 (3)
H14	1.4565	0.9239	0.7115	0.043*
H2	1.141 (3)	0.809 (2)	0.660 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0458 (3)	0.1068 (5)	0.0802 (4)	0.0259 (3)	−0.0248 (3)	−0.0205 (4)
N1	0.0269 (6)	0.0390 (7)	0.0413 (7)	0.0161 (5)	0.0021 (5)	−0.0002 (6)
N2	0.0270 (6)	0.0385 (7)	0.0425 (7)	0.0179 (5)	0.0005 (5)	−0.0022 (6)
N3	0.0471 (8)	0.0356 (7)	0.0476 (8)	0.0178 (6)	0.0149 (7)	−0.0033 (6)
O1	0.0527 (8)	0.0596 (8)	0.0656 (9)	0.0360 (7)	0.0091 (7)	−0.0089 (7)
O2	0.0986 (13)	0.0879 (11)	0.0505 (9)	0.0534 (10)	0.0138 (8)	−0.0181 (8)
O3	0.0364 (6)	0.0568 (8)	0.0598 (8)	0.0295 (6)	0.0082 (6)	0.0016 (6)
O4	0.0368 (6)	0.0450 (7)	0.0554 (7)	0.0237 (5)	0.0024 (5)	−0.0080 (5)
C1	0.0283 (7)	0.0294 (7)	0.0337 (7)	0.0125 (6)	0.0087 (6)	0.0057 (6)
C2	0.0349 (8)	0.0296 (7)	0.0366 (8)	0.0133 (6)	0.0100 (6)	0.0028 (6)
C3	0.0387 (9)	0.0365 (8)	0.0385 (9)	0.0094 (7)	0.0029 (7)	−0.0023 (7)
C4	0.0280 (7)	0.0411 (9)	0.0454 (9)	0.0100 (7)	0.0014 (7)	0.0048 (7)
C5	0.0293 (7)	0.0343 (8)	0.0452 (9)	0.0151 (6)	0.0110 (6)	0.0093 (7)
C6	0.0297 (7)	0.0334 (7)	0.0345 (8)	0.0140 (6)	0.0074 (6)	0.0015 (6)
C7	0.0290 (7)	0.0356 (8)	0.0371 (8)	0.0178 (6)	0.0081 (6)	0.0030 (6)
C8	0.0296 (7)	0.0394 (8)	0.0344 (8)	0.0159 (6)	0.0080 (6)	0.0024 (6)
C9	0.0294 (7)	0.0370 (8)	0.0330 (8)	0.0126 (6)	0.0060 (6)	0.0035 (6)
C10	0.0402 (9)	0.0535 (10)	0.0380 (9)	0.0191 (8)	0.0088 (7)	−0.0043 (7)
C11	0.0483 (10)	0.0603 (11)	0.0339 (9)	0.0147 (9)	0.0008 (8)	−0.0090 (8)
C12	0.0338 (8)	0.0557 (11)	0.0412 (9)	0.0133 (8)	−0.0040 (7)	0.0026 (8)
C13	0.0320 (8)	0.0511 (10)	0.0471 (10)	0.0187 (7)	0.0053 (7)	0.0038 (8)
C14	0.0320 (8)	0.0390 (8)	0.0360 (8)	0.0145 (6)	0.0050 (6)	−0.0011 (6)

Geometric parameters (Å, º) top

Cl1—C12	1.7399 (17)	C4—C5	1.389 (2)
N1—C7	1.266 (2)	C4—H4	0.9300
N1—N2	1.3714 (17)	C5—C6	1.388 (2)
N2—C8	1.351 (2)	C6—H6	0.9300
N2—H2	0.896 (10)	C7—H7	0.9300
N3—O2	1.2160 (19)	C8—C9	1.489 (2)
N3—O1	1.2245 (19)	C9—C10	1.387 (2)
N3—C2	1.456 (2)	C9—C14	1.390 (2)
O3—C5	1.3447 (19)	C10—C11	1.385 (2)
O3—H3	0.8200	C10—H10	0.9300
O4—C8	1.2285 (18)	C11—C12	1.372 (3)
C1—C6	1.391 (2)	C11—H11	0.9300
C1—C2	1.401 (2)	C12—C13	1.375 (3)
C1—C7	1.476 (2)	C13—C14	1.383 (2)
C2—C3	1.388 (2)	C13—H13	0.9300
C3—C4	1.375 (2)	C14—H14	0.9300
C3—H3A	0.9300

C7—N1—N2	116.59 (12)	C1—C6—H6	118.8
C8—N2—N1	118.41 (12)	N1—C7—C1	117.56 (13)
C8—N2—H2	122.9 (16)	N1—C7—H7	121.2
N1—N2—H2	118.7 (16)	C1—C7—H7	121.2
O2—N3—O1	121.99 (15)	O4—C8—N2	122.68 (14)
O2—N3—C2	118.32 (15)	O4—C8—C9	120.98 (14)
O1—N3—C2	119.67 (14)	N2—C8—C9	116.33 (13)
C5—O3—H3	109.5	C10—C9—C14	119.36 (14)
C6—C1—C2	116.51 (13)	C10—C9—C8	117.71 (14)
C6—C1—C7	117.54 (13)	C14—C9—C8	122.85 (14)
C2—C1—C7	125.89 (13)	C11—C10—C9	120.34 (16)
C3—C2—C1	121.43 (14)	C11—C10—H10	119.8
C3—C2—N3	115.96 (14)	C9—C10—H10	119.8
C1—C2—N3	122.59 (14)	C12—C11—C10	118.85 (16)
C4—C3—C2	120.83 (15)	C12—C11—H11	120.6
C4—C3—H3A	119.6	C10—C11—H11	120.6
C2—C3—H3A	119.6	C11—C12—C13	122.33 (16)
C3—C4—C5	119.00 (14)	C11—C12—Cl1	118.73 (14)
C3—C4—H4	120.5	C13—C12—Cl1	118.92 (15)
C5—C4—H4	120.5	C12—C13—C14	118.43 (16)
O3—C5—C6	116.31 (14)	C12—C13—H13	120.8
O3—C5—C4	123.86 (14)	C14—C13—H13	120.8
C6—C5—C4	119.83 (14)	C13—C14—C9	120.67 (15)
C5—C6—C1	122.38 (14)	C13—C14—H14	119.7
C5—C6—H6	118.8	C9—C14—H14	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	1.89	2.7093 (17)	174
N2—H2···O1ⁱⁱ	0.90 (1)	2.29 (1)	3.1649 (18)	165 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀ClN₃O₄
M_r	319.70
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.5386 (2), 8.1677 (2), 12.3435 (4)
α, β, γ (°)	90.820 (3), 106.056 (2), 109.014 (2)
V (Å³)	685.95 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1K diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.934, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	4267, 2933, 2444
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.04
No. of reflections	2933
No. of parameters	203
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)	0.31, −0.37

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
O3—H3···O4ⁱ	0.82	1.89	2.7093 (17)	173.7
N2—H2···O1ⁱⁱ	0.896 (10)	2.290 (11)	3.1649 (18)	165 (2)

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

Acknowledgements

The Vital Foundation of Ankang University (project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02 J K202) are gratefully acknowledged.

References

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