(E)-N′-[1-(4-Chloro­phen­yl)ethyl­idene]-2-hydroxy­benzohydrazide

Li, M.-L.; Huang, X.; Feng, R.-K.

doi:10.1107/S1600536809002311

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o369

doi:10.1107/S1600536809002311

Open

access

(E)-N′-[1-(4-Chlorophenyl)ethylidene]-2-hydroxybenzohydrazide

Man-Lin Li,^a ^* Xianqiang Huang ^b and Ruo-Kun Feng ^b

^aCollege of Science, Northwest A and F University, Yangling, Shaanxi 712100, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: hxqiang2005@yahoo.com.cn

(Received 2 December 2008; accepted 18 January 2009; online 23 January 2009)

In the title compound, C₁₅H₁₃ClN₂O₂, the dihedral angle between the two benzene rings is 7.0 (1)°. An intramolecular N—H⋯O hydrogen bond is present and intermolecular O—H⋯O hydrogen bonds link the molecules into chains along [001].

Related literature

For related literature, see: Sumita et al. (1999 ). For the crystal structure of the closely related compound (E)-2-hydroxy-N′-(2-naphthylmethylene)benzohydrazide, see: Qiu et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₂
M_r = 288.72
Monoclinic, C 2/c
a = 27.900 (3) Å
b = 7.880 (1) Å
c = 13.4899 (15) Å
β = 113.530 (2)°
V = 2719.2 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 (2) K
0.35 × 0.17 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.907, T_max = 0.980
4744 measured reflections
1663 independent reflections
901 reflections with I > 2σ(I)
R_int = 0.082
θ_max = 22.0°

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.266
S = 0.96
1663 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.33 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
N1—H1⋯O2	0.86	1.96	2.645 (6)	135
O2—H2⋯O1ⁱ	0.82	1.92	2.676 (6)	153
Symmetry code: (i) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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 I, global. DOI: 10.1107/S1600536809002311/bi2333sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002311/bi2333Isup2.hkl

checkCIF report

Comment top

Salicyloyl hydrazide is an important organic intermediate, which can act as moulding board in inorganic complexes (Sumita et al., 1999). The title compound was obtained by reaction of salicyloyl hydrazide and 1-(4-chlorophenyl)ethanone. The bond lengths and angles are normal and comparable to those in the previously reported compound (E)-2-hydroxy-N'-(2-naphthylmethylene)-benzohydrazide (Qiu et al., 2006).

In the crystal structure, typical intramolecular N—H···O hydrogen bonds exist, and intermolecular O—H···O hydrogen bonds link the molecules into one-dimensional chains along [001].

Related literature top

For related literature, see: Sumita et al. (1999). For the crystal structure of the closely related compound (E)-2-hydroxy-N'-(2-naphthylmethylene)benzohydrazide, see: Qiu et al. (2006).

Experimental top

Salicyloyl hydrazide (0.3 mmol) and freshly prepared 1-(4-chlorophenyl)ethanone (0.3 mmol) were mixed in a 50 ml flask. After stirring for 30 min at 353 K, the mixture was cooled slowly to room temperature and the product was recrystallized from ethanol, affording the title compound as a green crystalline solid. Elemental analysis calculated: C 62.40, H 4.54, N 9.70%; found: C 62.58, H 4.45, N 9.64%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. Molecular structure with displacement ellipsoids drawn at 30% probability for non-H atoms.

(E)-N'-[1-(4-Chlorophenyl)ethylidene]-2-hydroxybenzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O₂	F(000) = 1200
M_r = 288.72	D_x = 1.411 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 951 reflections
a = 27.900 (3) Å	θ = 2.7–25.1°
b = 7.880 (1) Å	µ = 0.28 mm⁻¹
c = 13.4899 (15) Å	T = 293 K
β = 113.530 (2)°	Block, green
V = 2719.2 (5) Å³	0.35 × 0.17 × 0.07 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	1663 independent reflections
Radiation source: fine-focus sealed tube	901 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 22.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→20
T_min = 0.907, T_max = 0.980	k = −8→8
4744 measured reflections	l = −14→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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.266	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.1726P)²] where P = (F_o² + 2F_c²)/3
1663 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O₂	V = 2719.2 (5) Å³
M_r = 288.72	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.900 (3) Å	µ = 0.28 mm⁻¹
b = 7.880 (1) Å	T = 293 K
c = 13.4899 (15) Å	0.35 × 0.17 × 0.07 mm
β = 113.530 (2)°

Data collection top

Bruker SMART CCD diffractometer	1663 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	901 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.980	R_int = 0.082
4744 measured reflections	θ_max = 22.0°

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.266	H-atom parameters constrained
S = 0.96	Δρ_max = 0.33 e Å⁻³
1663 reflections	Δρ_min = −0.37 e Å⁻³
182 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	−0.16974 (8)	0.5453 (3)	−0.40292 (16)	0.0745 (9)
N1	0.07264 (19)	0.1148 (7)	0.0780 (4)	0.0390 (15)
H1	0.0712	0.1193	0.1404	0.047*
N2	0.0332 (2)	0.1842 (7)	−0.0112 (4)	0.0372 (15)
O1	0.11636 (19)	0.0271 (8)	−0.0221 (4)	0.0714 (19)
O2	0.11905 (18)	0.0618 (6)	0.2888 (3)	0.0531 (15)
H2	0.1252	0.0612	0.3535	0.080*
C1	0.1133 (2)	0.0401 (10)	0.0666 (5)	0.0422 (19)
C2	0.1557 (2)	−0.0358 (9)	0.1654 (5)	0.0400 (18)
C3	0.1585 (2)	−0.0201 (9)	0.2719 (5)	0.0405 (19)
C4	0.2007 (3)	−0.0898 (10)	0.3581 (5)	0.050 (2)
H4	0.2027	−0.0789	0.4283	0.060*
C5	0.2391 (3)	−0.1741 (11)	0.3394 (6)	0.063 (2)
H5	0.2671	−0.2198	0.3975	0.075*
C6	0.2372 (3)	−0.1928 (11)	0.2365 (6)	0.060 (2)
H6	0.2627	−0.2543	0.2242	0.071*
C7	0.1960 (3)	−0.1174 (9)	0.1511 (6)	0.0457 (19)
H7	0.1958	−0.1225	0.0820	0.055*
C8	−0.0107 (3)	0.2598 (11)	0.1122 (5)	0.056 (2)
H8A	−0.0043	0.1505	0.1465	0.084*
H8B	−0.0452	0.2971	0.1005	0.084*
H8C	0.0145	0.3397	0.1578	0.084*
C9	−0.0057 (2)	0.2471 (9)	0.0044 (5)	0.0405 (18)
C10	−0.0473 (3)	0.3259 (9)	−0.0938 (5)	0.0387 (18)
C11	−0.0867 (3)	0.4294 (9)	−0.0915 (5)	0.046 (2)
H11	−0.0883	0.4545	−0.0254	0.055*
C12	−0.1242 (3)	0.4970 (10)	−0.1857 (6)	0.052 (2)
H12	−0.1503	0.5674	−0.1824	0.063*
C13	−0.1227 (3)	0.4592 (9)	−0.2842 (5)	0.0430 (19)
C14	−0.0845 (3)	0.3575 (10)	−0.2901 (5)	0.052 (2)
H14	−0.0827	0.3366	−0.3563	0.062*
C15	−0.0479 (3)	0.2847 (9)	−0.1954 (5)	0.0450 (19)
H15	−0.0236	0.2077	−0.2001	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0664 (15)	0.088 (2)	0.0516 (14)	0.0085 (12)	0.0054 (11)	0.0142 (12)
N1	0.039 (3)	0.058 (4)	0.023 (3)	0.000 (3)	0.016 (3)	0.002 (3)
N2	0.038 (3)	0.043 (4)	0.032 (3)	−0.001 (3)	0.016 (3)	0.001 (3)
O1	0.061 (3)	0.136 (6)	0.026 (3)	0.018 (3)	0.027 (3)	0.006 (3)
O2	0.062 (3)	0.078 (4)	0.025 (2)	0.006 (3)	0.023 (2)	0.005 (2)
C1	0.038 (4)	0.065 (5)	0.028 (4)	−0.011 (4)	0.018 (3)	−0.006 (3)
C2	0.036 (4)	0.060 (5)	0.028 (4)	−0.007 (4)	0.016 (3)	0.003 (3)
C3	0.038 (4)	0.053 (5)	0.036 (4)	−0.003 (3)	0.020 (3)	0.002 (3)
C4	0.057 (5)	0.053 (6)	0.034 (4)	−0.007 (4)	0.013 (4)	0.006 (4)
C5	0.045 (5)	0.084 (7)	0.054 (5)	0.009 (4)	0.014 (4)	0.015 (5)
C6	0.040 (5)	0.084 (7)	0.055 (5)	0.006 (4)	0.019 (4)	0.008 (5)
C7	0.051 (5)	0.046 (5)	0.047 (4)	−0.001 (4)	0.027 (4)	−0.004 (4)
C8	0.056 (5)	0.080 (7)	0.037 (4)	−0.001 (4)	0.025 (4)	0.006 (4)
C9	0.042 (4)	0.049 (5)	0.033 (4)	−0.013 (4)	0.018 (3)	−0.007 (3)
C10	0.042 (4)	0.050 (5)	0.028 (4)	−0.008 (4)	0.019 (3)	0.000 (3)
C11	0.044 (4)	0.059 (6)	0.038 (4)	0.001 (4)	0.020 (4)	−0.007 (4)
C12	0.048 (5)	0.057 (6)	0.052 (5)	0.003 (4)	0.021 (4)	0.006 (4)
C13	0.037 (4)	0.041 (5)	0.042 (4)	−0.005 (4)	0.006 (3)	0.006 (4)
C14	0.060 (5)	0.064 (6)	0.033 (4)	−0.003 (4)	0.021 (4)	0.002 (4)
C15	0.042 (4)	0.061 (6)	0.035 (4)	0.008 (4)	0.019 (3)	0.002 (4)

Geometric parameters (Å, º) top

Cl1—C13	1.752 (7)	C6—H6	0.930
N1—C1	1.340 (8)	C7—H7	0.930
N1—N2	1.379 (7)	C8—C9	1.518 (8)
N1—H1	0.860	C8—H8A	0.960
N2—C9	1.284 (8)	C8—H8B	0.960
O1—C1	1.237 (7)	C8—H8C	0.960
O2—C3	1.372 (8)	C9—C10	1.503 (9)
O2—H2	0.820	C10—C11	1.380 (9)
C1—C2	1.508 (9)	C10—C15	1.403 (8)
C2—C7	1.374 (9)	C11—C12	1.390 (9)
C2—C3	1.412 (9)	C11—H11	0.930
C3—C4	1.395 (9)	C12—C13	1.379 (10)
C4—C5	1.367 (10)	C12—H12	0.930
C4—H4	0.930	C13—C14	1.361 (10)
C5—C6	1.375 (10)	C14—C15	1.400 (9)
C5—H5	0.930	C14—H14	0.930
C6—C7	1.395 (9)	C15—H15	0.930

C1—N1—N2	119.4 (5)	C9—C8—H8B	109.5
C1—N1—H1	120.3	H8A—C8—H8B	109.5
N2—N1—H1	120.3	C9—C8—H8C	109.5
C9—N2—N1	116.2 (5)	H8A—C8—H8C	109.5
C3—O2—H2	109.5	H8B—C8—H8C	109.5
O1—C1—N1	122.4 (6)	N2—C9—C10	114.8 (5)
O1—C1—C2	119.3 (6)	N2—C9—C8	126.1 (6)
N1—C1—C2	118.3 (5)	C10—C9—C8	118.9 (6)
C7—C2—C3	117.8 (6)	C11—C10—C15	117.4 (6)
C7—C2—C1	117.3 (5)	C11—C10—C9	124.5 (5)
C3—C2—C1	124.8 (6)	C15—C10—C9	118.0 (6)
O2—C3—C4	120.8 (6)	C10—C11—C12	121.4 (6)
O2—C3—C2	119.2 (6)	C10—C11—H11	119.3
C4—C3—C2	120.0 (6)	C12—C11—H11	119.3
C5—C4—C3	120.0 (6)	C13—C12—C11	119.8 (7)
C5—C4—H4	120.0	C13—C12—H12	120.1
C3—C4—H4	120.0	C11—C12—H12	120.1
C4—C5—C6	121.3 (7)	C14—C13—C12	120.7 (6)
C4—C5—H5	119.3	C14—C13—Cl1	119.6 (5)
C6—C5—H5	119.3	C12—C13—Cl1	119.8 (6)
C5—C6—C7	118.4 (7)	C13—C14—C15	119.4 (6)
C5—C6—H6	120.8	C13—C14—H14	120.3
C7—C6—H6	120.8	C15—C14—H14	120.3
C2—C7—C6	122.3 (6)	C14—C15—C10	121.1 (7)
C2—C7—H7	118.8	C14—C15—H15	119.4
C6—C7—H7	118.8	C10—C15—H15	119.4
C9—C8—H8A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.96	2.645 (6)	135
O2—H2···O1ⁱ	0.82	1.92	2.676 (6)	153

Symmetry code: (i) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₂
M_r	288.72
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	27.900 (3), 7.880 (1), 13.4899 (15)
β (°)	113.530 (2)
V (Å³)	2719.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.35 × 0.17 × 0.07

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.907, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	4744, 1663, 901
R_int	0.082
θ_max (°)	22.0
(sin θ/λ)_max (Å⁻¹)	0.526

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.266, 0.96
No. of reflections	1663
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.37

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
N1—H1···O2	0.86	1.96	2.645 (6)	135.2
O2—H2···O1ⁱ	0.82	1.92	2.676 (6)	152.5

Symmetry code: (i) x, −y, z+1/2.

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X051040).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Qiu, X.-Y., Luo, Z.-G., Yang, S.-L. & Liu, W.-S. (2006). Acta Cryst. E62, o3531–o3532. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sumita, N. R., Munshi, K. N., Nageswara, R. N., Bhadbhade, M. M. & Suresh, E. (1999). Polyhedron, 18, 2491–2497. Google Scholar