N′-[1-(4-Chloro­phen­yl)ethyl­idene]benzo­hydrazide

Zeng, S.; Li, L.

doi:10.1107/S1600536811042887

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3043

doi:10.1107/S1600536811042887

Open

access

N′-[1-(4-Chlorophenyl)ethylidene]benzohydrazide

Suyuan Zeng ^a ^* and Lei Li ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: drzengsy@163.com

(Received 30 September 2011; accepted 17 October 2011; online 29 October 2011)

In the title molecule, C₁₅H₁₃ClN₂O, the two benzene rings form a dihedral angle of 5.48 (4)°. In the crystal, N—H⋯O hydrogen bonds link molecules related by translation along the a axis into chains, which are further aggregated into layers parallel to the ac plane through weak C—H⋯O and C—H⋯N interactions.

Related literature

For applications of Schiff base derivatives and their complexes, see: Chavan et al. (2011 ); Ray et al. (2011 ). For the crystal structures of related compounds, see: Nie (2008 ); Fun et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O
M_r = 272.72
Monoclinic, P 2₁ /c
a = 5.0714 (6) Å
b = 31.430 (3) Å
c = 8.4128 (7) Å
β = 94.388 (1)°
V = 1337.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-etector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.897, T_max = 0.967
6717 measured reflections
2322 independent reflections
711 reflections with I > 2σ(I)
R_int = 0.156

Refinement

R[F² > 2σ(F²)] = 0.089
wR(F²) = 0.205
S = 1.01
2322 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.32	3.067 (6)	145
C9—H9C⋯N2ⁱ	0.96	2.53	3.452 (8)	162
C15—H15⋯O1ⁱⁱ	0.93	2.61	3.483 (7)	157
Symmetry codes: (i) x-1, y, z; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536811042887/cv5164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042887/cv5164Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042887/cv5164Isup3.cml

checkCIF report

Comment top

Schiff bases have various applications in the study of biological processes and in pharmacology (Chavan et al., 2011; Ray et al., 2011). We report here the crystal structure of the title Schiff base compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to the values observed in similar compounds (Nie, 2008; Fun et al., 2008). The C═N (C8═N2) bond length in the molecule is 1.270 (7) Å showing the double-bond character. Meanwhile, the dihedral angle between the benzene rings C2–C7 and C10–C15 is 5.48 (4)°.

In the crystal stucture, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis a into chains, which are further aggregated into layers parallel to ac plane through the weak C—H···O(N) interactions (Table 1).

Related literature top

For applications of Schiff base derivatives and their complexes, see: Chavan et al. (2011); Ray et al. (2011). For the crystal structures of related compounds, see: Nie (2008); Fun et al. (2008).

Experimental top

Benzohydrazide (5.0 mmol), 20 ml ethanol and 4-chloroacetophenone (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. View of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

N'-[1-(4-Chlorophenyl)ethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O	F(000) = 568
M_r = 272.72	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.0714 (6) Å	Cell parameters from 385 reflections
b = 31.430 (3) Å	θ = 2.6–18.2°
c = 8.4128 (7) Å	µ = 0.28 mm⁻¹
β = 94.388 (1)°	T = 298 K
V = 1337.0 (2) Å³	Needle, colourless
Z = 4	0.40 × 0.30 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-etector diffractometer	2322 independent reflections
Radiation source: fine-focus sealed tube	711 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.156
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
T_min = 0.897, T_max = 0.967	k = −36→37
6717 measured reflections	l = −9→9

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)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.205	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0367P)²] where P = (F_o² + 2F_c²)/3
2322 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O	V = 1337.0 (2) Å³
M_r = 272.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.0714 (6) Å	µ = 0.28 mm⁻¹
b = 31.430 (3) Å	T = 298 K
c = 8.4128 (7) Å	0.40 × 0.30 × 0.12 mm
β = 94.388 (1)°

Data collection top

Bruker SMART APEX CCD area-etector diffractometer	2322 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	711 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.967	R_int = 0.156
6717 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.089	0 restraints
wR(F²) = 0.205	H-atom parameters constrained
S = 1.01	Δρ_max = 0.31 e Å⁻³
2322 reflections	Δρ_min = −0.24 e Å⁻³
173 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	0.1612 (9)	0.19148 (16)	0.2256 (5)	0.0650 (15)
H1	0.0012	0.1841	0.1975	0.078*
N2	0.2278 (10)	0.23422 (17)	0.2404 (6)	0.0623 (14)
O1	0.5839 (9)	0.17193 (12)	0.2838 (5)	0.0807 (14)
Cl1	0.3944 (4)	0.44187 (5)	0.2883 (3)	0.1218 (10)
C1	0.3466 (15)	0.1622 (2)	0.2551 (7)	0.0666 (18)
C2	0.2677 (14)	0.11724 (19)	0.2454 (9)	0.072 (2)
C3	0.4245 (14)	0.0876 (2)	0.3254 (8)	0.091 (2)
H3	0.5794	0.0961	0.3833	0.109*
C4	0.354 (2)	0.0454 (2)	0.3206 (11)	0.115 (3)
H4	0.4591	0.0259	0.3790	0.138*
C5	0.135 (2)	0.0313 (3)	0.2335 (14)	0.128 (4)
H5	0.0881	0.0027	0.2317	0.154*
C6	−0.0118 (16)	0.0606 (3)	0.1496 (12)	0.130 (3)
H6	−0.1606	0.0520	0.0864	0.156*
C7	0.0548 (14)	0.1034 (2)	0.1558 (9)	0.097 (3)
H7	−0.0502	0.1228	0.0966	0.116*
C8	0.0706 (13)	0.2614 (2)	0.1746 (8)	0.0627 (17)
C9	−0.1756 (12)	0.24969 (16)	0.0768 (8)	0.083 (2)
H9A	−0.1467	0.2240	0.0190	0.124*
H9B	−0.2230	0.2722	0.0030	0.124*
H9C	−0.3161	0.2453	0.1453	0.124*
C10	0.1404 (12)	0.30593 (19)	0.2013 (8)	0.0571 (17)
C11	0.3468 (14)	0.3164 (2)	0.3061 (9)	0.088 (2)
H11	0.4385	0.2948	0.3619	0.106*
C12	0.4259 (13)	0.3580 (2)	0.3330 (8)	0.090 (2)
H12	0.5711	0.3639	0.4040	0.108*
C13	0.2931 (16)	0.39022 (19)	0.2566 (9)	0.0744 (19)
C14	0.0872 (14)	0.3808 (2)	0.1543 (9)	0.083 (2)
H14	−0.0043	0.4027	0.0999	0.100*
C15	0.0069 (12)	0.3392 (2)	0.1273 (7)	0.077 (2)
H15	−0.1404	0.3337	0.0576	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.046 (3)	0.067 (4)	0.079 (4)	0.003 (3)	−0.015 (3)	−0.008 (3)
N2	0.055 (4)	0.070 (4)	0.060 (3)	0.001 (3)	−0.010 (3)	0.001 (3)
O1	0.063 (3)	0.077 (3)	0.100 (4)	0.000 (2)	−0.009 (3)	0.002 (2)
Cl1	0.1365 (18)	0.0779 (13)	0.147 (2)	−0.0169 (12)	−0.0117 (16)	−0.0044 (13)
C1	0.062 (5)	0.072 (5)	0.066 (5)	0.001 (5)	0.007 (5)	−0.001 (4)
C2	0.051 (5)	0.060 (5)	0.106 (6)	0.002 (4)	0.007 (5)	−0.006 (4)
C3	0.099 (6)	0.081 (5)	0.088 (6)	0.012 (5)	−0.016 (5)	−0.008 (5)
C4	0.142 (9)	0.064 (6)	0.138 (8)	0.013 (6)	−0.001 (7)	0.009 (5)
C5	0.109 (8)	0.072 (6)	0.208 (12)	−0.015 (6)	0.043 (8)	−0.014 (7)
C6	0.098 (7)	0.089 (7)	0.201 (11)	−0.007 (6)	−0.003 (7)	−0.030 (7)
C7	0.056 (5)	0.078 (5)	0.155 (8)	0.011 (4)	−0.007 (5)	−0.029 (5)
C8	0.039 (4)	0.076 (5)	0.071 (5)	0.002 (4)	−0.009 (4)	−0.003 (4)
C9	0.071 (5)	0.079 (4)	0.096 (6)	−0.004 (4)	−0.009 (5)	0.014 (4)
C10	0.033 (4)	0.066 (5)	0.070 (5)	0.001 (3)	−0.002 (4)	−0.007 (4)
C11	0.087 (6)	0.061 (5)	0.112 (6)	0.011 (4)	−0.019 (5)	0.001 (4)
C12	0.085 (5)	0.087 (5)	0.092 (6)	0.005 (5)	−0.035 (5)	−0.016 (5)
C13	0.066 (5)	0.068 (5)	0.090 (5)	−0.006 (4)	0.010 (5)	0.006 (4)
C14	0.073 (5)	0.069 (5)	0.105 (6)	−0.006 (4)	−0.010 (5)	0.027 (4)
C15	0.065 (5)	0.069 (5)	0.094 (6)	0.004 (4)	−0.016 (4)	0.008 (4)

Geometric parameters (Å, º) top

N1—C1	1.326 (6)	C7—H7	0.9300
N1—N2	1.388 (5)	C8—C10	1.458 (7)
N1—H1	0.8600	C8—C9	1.488 (8)
N2—C8	1.266 (6)	C9—H9A	0.9600
O1—C1	1.248 (6)	C9—H9B	0.9600
Cl1—C13	1.717 (6)	C9—H9C	0.9600
C1—C2	1.468 (7)	C10—C11	1.357 (7)
C2—C7	1.341 (8)	C10—C15	1.369 (7)
C2—C3	1.368 (8)	C11—C12	1.382 (7)
C3—C4	1.374 (9)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.351 (8)
C4—C5	1.357 (9)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.335 (8)
C5—C6	1.350 (10)	C14—C15	1.383 (7)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.385 (8)	C15—H15	0.9300
C6—H6	0.9300

C1—N1—N2	119.4 (5)	N2—C8—C9	123.3 (6)
C1—N1—H1	120.3	C10—C8—C9	120.4 (6)
N2—N1—H1	120.3	C8—C9—H9A	109.5
C8—N2—N1	118.2 (5)	C8—C9—H9B	109.5
O1—C1—N1	121.7 (6)	H9A—C9—H9B	109.5
O1—C1—C2	120.1 (6)	C8—C9—H9C	109.5
N1—C1—C2	118.1 (6)	H9A—C9—H9C	109.5
C7—C2—C3	117.9 (6)	H9B—C9—H9C	109.5
C7—C2—C1	123.2 (7)	C11—C10—C15	116.1 (6)
C3—C2—C1	118.8 (7)	C11—C10—C8	120.0 (6)
C2—C3—C4	120.1 (7)	C15—C10—C8	123.9 (6)
C2—C3—H3	120.0	C10—C11—C12	122.4 (6)
C4—C3—H3	120.0	C10—C11—H11	118.8
C5—C4—C3	122.3 (8)	C12—C11—H11	118.8
C5—C4—H4	118.9	C13—C12—C11	120.2 (6)
C3—C4—H4	118.9	C13—C12—H12	119.9
C6—C5—C4	116.9 (9)	C11—C12—H12	119.9
C6—C5—H5	121.5	C14—C13—C12	118.6 (6)
C4—C5—H5	121.5	C14—C13—Cl1	121.3 (6)
C5—C6—C7	121.4 (9)	C12—C13—Cl1	120.1 (7)
C5—C6—H6	119.3	C13—C14—C15	121.4 (6)
C7—C6—H6	119.3	C13—C14—H14	119.3
C2—C7—C6	121.3 (7)	C15—C14—H14	119.3
C2—C7—H7	119.4	C10—C15—C14	121.2 (6)
C6—C7—H7	119.4	C10—C15—H15	119.4
N2—C8—C10	116.3 (6)	C14—C15—H15	119.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.32	3.067 (6)	145
C9—H9C···N2ⁱ	0.96	2.53	3.452 (8)	162
C15—H15···O1ⁱⁱ	0.93	2.61	3.483 (7)	157

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O
M_r	272.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.0714 (6), 31.430 (3), 8.4128 (7)
β (°)	94.388 (1)
V (Å³)	1337.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.40 × 0.30 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-etector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.897, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	6717, 2322, 711
R_int	0.156
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.089, 0.205, 1.01
No. of reflections	2322
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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···O1ⁱ	0.86	2.32	3.067 (6)	145.4
C9—H9C···N2ⁱ	0.96	2.53	3.452 (8)	161.5
C15—H15···O1ⁱⁱ	0.93	2.61	3.483 (7)	157.0

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

Acknowledgements

The authors acknowledge financial support from Liaocheng University.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chavan, S. S., Sawant, S. K., Sawant, V. A. & Lahiri, G. K. (2011). Inorg. Chem. Commun. 14, 1373–1376. Web of Science CSD CrossRef CAS Google Scholar
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nie, Y. (2008). Acta Cryst. E64, o471. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ray, A., Rosair, G. M., Pilet, G., Dede, B., Gomez-Garcia, C. J., Signorella, S., Bellu, S. & Mitra, S. (2011). Inorg. Chim. Acta, 375, 20–30. Web of Science CSD CrossRef CAS 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