(E)-N′-(5-Chloro-2-hydroxy­benzyl­idene)-2-nitro­benzohydrazide

Qian, H.-Y.; Qu, D.-P.

doi:10.1107/S1600536809033108

organic compounds

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Volume 65| Part 9| September 2009| Page o2239

doi:10.1107/S1600536809033108

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(E)-N′-(5-Chloro-2-hydroxybenzylidene)-2-nitrobenzohydrazide

Heng-Yu Qian ^a ^* and Da-Ping Qu ^b

^aKey Laboratory of Surface and Interface Science of Henan, School of Material & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China, and ^bDepartment of Chemistry, Dalian Teacher College, Dalian 116000, People's Republic of China
^*Correspondence e-mail: hengyu_qian@126.com

(Received 19 August 2009; accepted 19 August 2009; online 26 August 2009)

In the title Schiff base compound, C₁₄H₁₀ClN₃O₄, the molecule adopts an E geometry with respect to the C=N bond and an intramolecular O—H⋯N hydrogen bond is present. The benzene rings form a dihedral angle of 73.4 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

Related literature

For a related structure and background, see: Qian & Qu (2009 ).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₄
M_r = 319.70
Triclinic, $[P \overline 1]$
a = 7.353 (1) Å
b = 10.005 (2) Å
c = 10.273 (2) Å
α = 93.393 (3)°
β = 108.144 (3)°
γ = 98.886 (4)°
V = 704.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.936, T_max = 0.944
4324 measured reflections
3004 independent reflections
2237 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.122
S = 1.02
3004 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.94	2.657 (2)	145
N2—H2⋯O2ⁱ	0.902 (10)	1.966 (11)	2.863 (2)	173 (3)
Symmetry code: (i) -x, -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/S1600536809033108/hb5055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033108/hb5055Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of Schiff bases (Qian & Qu, 2009), we now report the synthsis and structure of the title compound, (I), (Fig. 1).

In the title compound, the Schiff base molecule adopts an E geometry with respect to the CN bond, as shown in Fig. 1. There forms an intramolecular O—H···N hydrogen bond. The two benzene rings forms a dihedral angle of 73.4 (2)°. The dihedral angle between the O3/N3/O4 plane and the C9—C14 benzene ring is 23.2 (2)°. In the crystal structure, the adjacent two Schiff base molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form a dimer (Fig. 2).

Related literature top

For a related structure and background, see: Qian & Qu (2009).

Experimental top

2-Nitrobenzohydrazide (1 mmol, 0.181 g) and 5-chlorosalicylaldehyde (1 mmol, 0.156 g) were dissolved in anhydrous methanol (15 ml). The mixture was stirred for several minutes at room temperature. The product was isolated and recrystallized from methanol, colorless blocks of (I) were obtained after a week.

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 (I). Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonding is shown by dashed lines.
	Fig. 2. The molecular packing of (I), viewed along the b axis. Hydrogen bonding is shown in dashed lines.

(E)-N'-(5-Chloro-2-hydroxybenzylidene)-2-nitrobenzohydrazide top

Crystal data top

C₁₄H₁₀ClN₃O₄	Z = 2
M_r = 319.70	F(000) = 328
Triclinic, P1	D_x = 1.506 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.353 (1) Å	Cell parameters from 1356 reflections
b = 10.005 (2) Å	θ = 2.4–25.6°
c = 10.273 (2) Å	µ = 0.29 mm⁻¹
α = 93.393 (3)°	T = 298 K
β = 108.144 (3)°	Block, colorless
γ = 98.886 (4)°	0.23 × 0.20 × 0.20 mm
V = 704.9 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	3004 independent reflections
Radiation source: fine-focus sealed tube	2237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.936, T_max = 0.944	k = −9→12
4324 measured reflections	l = −13→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0501P)² + 0.3008P] where P = (F_o² + 2F_c²)/3
3004 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₄H₁₀ClN₃O₄	γ = 98.886 (4)°
M_r = 319.70	V = 704.9 (2) Å³
Triclinic, P1	Z = 2
a = 7.353 (1) Å	Mo Kα radiation
b = 10.005 (2) Å	µ = 0.29 mm⁻¹
c = 10.273 (2) Å	T = 298 K
α = 93.393 (3)°	0.23 × 0.20 × 0.20 mm
β = 108.144 (3)°

Data collection top

Bruker SMART CCD diffractometer	3004 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2237 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.944	R_int = 0.013
4324 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
3004 reflections	Δρ_min = −0.44 e Å⁻³
203 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
Cl1	0.54671 (11)	−0.14057 (9)	0.86494 (8)	0.0837 (3)
N1	0.1470 (2)	0.23302 (15)	0.43169 (16)	0.0372 (4)
N2	0.0876 (3)	0.35676 (17)	0.43461 (17)	0.0422 (4)
N3	0.3643 (3)	0.53956 (19)	0.2180 (2)	0.0510 (5)
O1	0.1405 (2)	−0.01201 (16)	0.31361 (15)	0.0534 (4)
H1	0.1202	0.0663	0.3150	0.080*
O2	−0.0068 (3)	0.53476 (15)	0.32927 (15)	0.0574 (5)
O3	0.4103 (3)	0.54714 (19)	0.34314 (18)	0.0735 (5)
O4	0.4446 (3)	0.6178 (2)	0.1575 (2)	0.0898 (7)
C1	0.2638 (3)	0.05581 (19)	0.5597 (2)	0.0383 (4)
C2	0.2290 (3)	−0.0378 (2)	0.4431 (2)	0.0428 (5)
C3	0.2854 (3)	−0.1637 (2)	0.4603 (3)	0.0543 (6)
H3	0.2585	−0.2270	0.3837	0.065*
C4	0.3798 (4)	−0.1956 (2)	0.5886 (3)	0.0615 (7)
H4	0.4185	−0.2796	0.5990	0.074*
C5	0.4176 (3)	−0.1023 (3)	0.7029 (3)	0.0551 (6)
C6	0.3583 (3)	0.0212 (2)	0.6893 (2)	0.0463 (5)
H6	0.3816	0.0820	0.7673	0.056*
C7	0.2062 (3)	0.18811 (19)	0.5484 (2)	0.0377 (4)
H7	0.2125	0.2412	0.6277	0.045*
C8	0.0525 (3)	0.4269 (2)	0.3254 (2)	0.0404 (5)
C9	0.0740 (3)	0.36796 (19)	0.19420 (19)	0.0369 (4)
C10	0.2071 (3)	0.43017 (19)	0.13654 (19)	0.0374 (4)
C11	0.2035 (3)	0.3885 (2)	0.0051 (2)	0.0461 (5)
H11	0.2919	0.4344	−0.0323	0.055*
C12	0.0674 (4)	0.2784 (2)	−0.0695 (2)	0.0529 (6)
H12	0.0638	0.2488	−0.1580	0.063*
C13	−0.0624 (4)	0.2123 (2)	−0.0142 (2)	0.0573 (6)
H13	−0.1526	0.1366	−0.0643	0.069*
C14	−0.0606 (4)	0.2574 (2)	0.1164 (2)	0.0516 (6)
H14	−0.1516	0.2126	0.1522	0.062*
H2	0.072 (4)	0.392 (3)	0.5126 (18)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0709 (5)	0.0970 (6)	0.0952 (6)	0.0360 (4)	0.0260 (4)	0.0547 (5)
N1	0.0494 (10)	0.0296 (8)	0.0381 (9)	0.0096 (7)	0.0212 (8)	0.0020 (7)
N2	0.0654 (11)	0.0356 (9)	0.0368 (9)	0.0178 (8)	0.0281 (8)	0.0055 (7)
N3	0.0529 (11)	0.0467 (11)	0.0539 (12)	0.0027 (9)	0.0224 (9)	−0.0015 (9)
O1	0.0639 (10)	0.0449 (9)	0.0481 (9)	0.0110 (8)	0.0156 (8)	−0.0083 (7)
O2	0.1017 (13)	0.0428 (9)	0.0476 (9)	0.0330 (9)	0.0414 (9)	0.0136 (7)
O3	0.0818 (13)	0.0720 (12)	0.0495 (10)	−0.0114 (10)	0.0125 (9)	−0.0109 (9)
O4	0.0946 (15)	0.0820 (14)	0.0882 (14)	−0.0283 (12)	0.0452 (12)	0.0039 (11)
C1	0.0381 (10)	0.0339 (10)	0.0461 (11)	0.0053 (8)	0.0189 (9)	0.0053 (8)
C2	0.0377 (11)	0.0351 (10)	0.0571 (13)	0.0023 (8)	0.0205 (10)	−0.0005 (9)
C3	0.0524 (13)	0.0341 (11)	0.0804 (17)	0.0077 (10)	0.0291 (13)	−0.0022 (11)
C4	0.0554 (14)	0.0390 (12)	0.103 (2)	0.0170 (11)	0.0389 (15)	0.0186 (13)
C5	0.0443 (12)	0.0553 (14)	0.0752 (16)	0.0167 (10)	0.0253 (12)	0.0291 (12)
C6	0.0459 (12)	0.0451 (12)	0.0527 (12)	0.0102 (9)	0.0207 (10)	0.0112 (10)
C7	0.0441 (11)	0.0336 (10)	0.0386 (10)	0.0053 (8)	0.0194 (9)	0.0001 (8)
C8	0.0553 (12)	0.0350 (10)	0.0369 (10)	0.0098 (9)	0.0227 (9)	0.0046 (8)
C9	0.0488 (11)	0.0337 (10)	0.0322 (9)	0.0115 (8)	0.0168 (8)	0.0035 (8)
C10	0.0444 (11)	0.0355 (10)	0.0349 (10)	0.0108 (8)	0.0150 (9)	0.0034 (8)
C11	0.0558 (13)	0.0521 (13)	0.0388 (11)	0.0154 (10)	0.0242 (10)	0.0080 (9)
C12	0.0706 (16)	0.0597 (14)	0.0300 (10)	0.0190 (12)	0.0163 (10)	−0.0004 (10)
C13	0.0663 (15)	0.0525 (14)	0.0424 (12)	−0.0003 (11)	0.0103 (11)	−0.0083 (10)
C14	0.0580 (14)	0.0488 (13)	0.0476 (12)	−0.0015 (10)	0.0229 (11)	−0.0004 (10)

Geometric parameters (Å, º) top

Cl1—C5	1.738 (3)	C4—C5	1.383 (4)
N1—C7	1.276 (2)	C4—H4	0.9300
N1—N2	1.377 (2)	C5—C6	1.373 (3)
N2—C8	1.336 (2)	C6—H6	0.9300
N2—H2	0.902 (10)	C7—H7	0.9300
N3—O3	1.217 (2)	C8—C9	1.503 (2)
N3—O4	1.221 (2)	C9—C14	1.380 (3)
N3—C10	1.460 (3)	C9—C10	1.383 (3)
O1—C2	1.347 (3)	C10—C11	1.380 (3)
O1—H1	0.8200	C11—C12	1.373 (3)
O2—C8	1.228 (2)	C11—H11	0.9300
C1—C6	1.389 (3)	C12—C13	1.364 (3)
C1—C2	1.407 (3)	C12—H12	0.9300
C1—C7	1.451 (3)	C13—C14	1.385 (3)
C2—C3	1.390 (3)	C13—H13	0.9300
C3—C4	1.367 (4)	C14—H14	0.9300
C3—H3	0.9300

C7—N1—N2	115.34 (15)	C1—C6—H6	119.8
C8—N2—N1	122.02 (15)	N1—C7—C1	121.21 (17)
C8—N2—H2	118.8 (18)	N1—C7—H7	119.4
N1—N2—H2	119.2 (18)	C1—C7—H7	119.4
O3—N3—O4	123.3 (2)	O2—C8—N2	120.66 (17)
O3—N3—C10	118.26 (18)	O2—C8—C9	120.00 (17)
O4—N3—C10	118.47 (19)	N2—C8—C9	119.22 (17)
C2—O1—H1	109.5	C14—C9—C10	117.09 (18)
C6—C1—C2	118.97 (19)	C14—C9—C8	119.38 (18)
C6—C1—C7	119.03 (18)	C10—C9—C8	122.92 (18)
C2—C1—C7	121.99 (18)	C11—C10—C9	122.36 (19)
O1—C2—C3	117.59 (19)	C11—C10—N3	117.72 (18)
O1—C2—C1	122.93 (18)	C9—C10—N3	119.85 (17)
C3—C2—C1	119.5 (2)	C12—C11—C10	119.0 (2)
C4—C3—C2	120.7 (2)	C12—C11—H11	120.5
C4—C3—H3	119.6	C10—C11—H11	120.5
C2—C3—H3	119.6	C13—C12—C11	120.11 (19)
C3—C4—C5	119.7 (2)	C13—C12—H12	119.9
C3—C4—H4	120.1	C11—C12—H12	119.9
C5—C4—H4	120.1	C12—C13—C14	120.3 (2)
C6—C5—C4	120.7 (2)	C12—C13—H13	119.9
C6—C5—Cl1	119.7 (2)	C14—C13—H13	119.9
C4—C5—Cl1	119.51 (19)	C9—C14—C13	121.1 (2)
C5—C6—C1	120.3 (2)	C9—C14—H14	119.4
C5—C6—H6	119.8	C13—C14—H14	119.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.94	2.657 (2)	145
N2—H2···O2ⁱ	0.90 (1)	1.97 (1)	2.863 (2)	173 (3)

Symmetry code: (i) −x, −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)	7.353 (1), 10.005 (2), 10.273 (2)
α, β, γ (°)	93.393 (3), 108.144 (3), 98.886 (4)
V (Å³)	704.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.936, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	4324, 3004, 2237
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 1.02
No. of reflections	3004
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)	0.30, −0.44

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···N1	0.82	1.94	2.657 (2)	145
N2—H2···O2ⁱ	0.902 (10)	1.966 (11)	2.863 (2)	173 (3)

Symmetry code: (i) −x, −y+1, −z+1.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Qian, H.-Y. & Qu, D.-P. (2009). Acta Cryst. E65, o2237. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2239

doi:10.1107/S1600536809033108

Open

access