2-Chloro-N′-(2,4-dichloro­benzyl­idene)benzohydrazide

Zhou, C.-S.; Yang, T.

doi:10.1107/S1600536810007531

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o752

doi:10.1107/S1600536810007531

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2-Chloro-N′-(2,4-dichlorobenzylidene)benzohydrazide

Cong-Shan Zhou ^a and Tao Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006, People's Republic of China
^*Correspondence e-mail: zhoucongsh@gmail.com

(Received 25 February 2010; accepted 27 February 2010; online 6 March 2010)

The title Schiff base compound, C₁₄H₉Cl₃N₂O, exists in a trans configuration with respect to the C=N bond and the dihedral angle between the two benzene rings is 13.5 (2)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link adjacent molecules into extended C(4) chains propagating along the c-axis direction.

Related literature

For a related structure and background material, see the previous paper: Zhou & Yang (2010 ).

Experimental

Crystal data

C₁₄H₉Cl₃N₂O
M_r = 327.58
Monoclinic, P 2₁ /c
a = 7.4737 (11) Å
b = 25.877 (4) Å
c = 8.1833 (12) Å
β = 116.013 (2)°
V = 1422.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.867, T_max = 0.883
7752 measured reflections
2828 independent reflections
2066 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.121
S = 1.02
2828 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.89 (1)	2.00 (1)	2.864 (3)	164 (3)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: 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/S1600536810007531/hb5344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007531/hb5344Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of Schiff bases (Zhou & Yang, 2010), the crystal structure of the title Schiff base, (I), derived from the condensing of 2,4-dichlorobenzaldehyde with 2-chlorobenzohydrazide in methanol is reported.

The molecule exists in a trans configuration with respect to the acyclic C═N bond. The molecule of the compound is distorted, with the dihedral angle between the two benzene rings of 13.5 (2)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds link adjacent molecules into extended chains along the c axis (Table 1 and Fig. 2).

Related literature top

For a related structure and background material, see the previous paper: Zhou & Yang (2010).

Experimental top

2,4-Dichlorobenzaldehyde (1.0 mmol, 175 mg) and 2-chlorobenzohydrazide (1.0 mmol, 170 mg) were dissolved in a methanol solution (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was left in air for a few days, yielding colourless blocks of (I).

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

2-Chloro-N'-(2,4-dichlorobenzylidene)benzohydrazide top

Crystal data top

C₁₄H₉Cl₃N₂O	F(000) = 664
M_r = 327.58	D_x = 1.530 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2111 reflections
a = 7.4737 (11) Å	θ = 3.0–24.9°
b = 25.877 (4) Å	µ = 0.64 mm⁻¹
c = 8.1833 (12) Å	T = 298 K
β = 116.013 (2)°	Block, colourless
V = 1422.3 (4) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	2828 independent reflections
Radiation source: fine-focus sealed tube	2066 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 26.2°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→7
T_min = 0.867, T_max = 0.883	k = −28→32
7752 measured reflections	l = −10→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0516P)² + 0.7512P] where P = (F_o² + 2F_c²)/3
2828 reflections	(Δ/σ)_max = 0.001
184 parameters	Δρ_max = 0.59 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₉Cl₃N₂O	V = 1422.3 (4) Å³
M_r = 327.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4737 (11) Å	µ = 0.64 mm⁻¹
b = 25.877 (4) Å	T = 298 K
c = 8.1833 (12) Å	0.23 × 0.20 × 0.20 mm
β = 116.013 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	2828 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2066 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.883	R_int = 0.029
7752 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.59 e Å⁻³
2828 reflections	Δρ_min = −0.36 e Å⁻³
184 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	0.19289 (14)	0.55576 (3)	0.33995 (10)	0.0770 (3)
Cl2	0.73603 (12)	0.52632 (3)	1.02156 (11)	0.0691 (3)
Cl3	0.07212 (14)	0.90788 (3)	0.33033 (13)	0.0715 (3)
H2	0.076 (5)	0.7358 (12)	0.209 (2)	0.080*
N1	0.1947 (3)	0.71586 (8)	0.4668 (3)	0.0436 (5)
N2	0.0880 (3)	0.74638 (8)	0.3170 (3)	0.0435 (5)
O1	0.0219 (3)	0.80567 (7)	0.4865 (2)	0.0554 (5)
C1	0.3509 (4)	0.63513 (10)	0.5759 (3)	0.0395 (6)
C2	0.3470 (4)	0.58197 (10)	0.5493 (3)	0.0438 (6)
C3	0.4627 (4)	0.54838 (10)	0.6852 (4)	0.0477 (7)
H3	0.4554	0.5129	0.6648	0.057*
C4	0.5895 (4)	0.56846 (11)	0.8522 (3)	0.0450 (6)
C5	0.6012 (4)	0.62076 (11)	0.8836 (4)	0.0482 (7)
H5	0.6895	0.6339	0.9961	0.058*
C6	0.4815 (4)	0.65335 (10)	0.7478 (3)	0.0444 (6)
H6	0.4874	0.6887	0.7707	0.053*
C7	0.2298 (4)	0.67024 (10)	0.4305 (3)	0.0421 (6)
H7	0.1777	0.6593	0.3102	0.051*
C8	0.0076 (4)	0.79055 (9)	0.3394 (3)	0.0419 (6)
C9	−0.1100 (4)	0.81908 (10)	0.1658 (3)	0.0421 (6)
C10	−0.0930 (4)	0.87193 (11)	0.1520 (4)	0.0510 (7)
C11	−0.2088 (6)	0.89765 (13)	−0.0095 (5)	0.0675 (9)
H11	−0.1944	0.9331	−0.0191	0.081*
C12	−0.3438 (6)	0.87046 (16)	−0.1536 (5)	0.0769 (11)
H12	−0.4230	0.8879	−0.2606	0.092*
C13	−0.3653 (5)	0.81802 (15)	−0.1446 (4)	0.0701 (10)
H13	−0.4571	0.8003	−0.2454	0.084*
C14	−0.2510 (4)	0.79142 (13)	0.0140 (3)	0.0557 (8)
H14	−0.2663	0.7559	0.0211	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0824 (6)	0.0591 (5)	0.0504 (5)	0.0065 (4)	−0.0068 (4)	−0.0140 (4)
Cl2	0.0573 (5)	0.0710 (5)	0.0564 (5)	0.0074 (4)	0.0042 (4)	0.0240 (4)
Cl3	0.0819 (6)	0.0509 (4)	0.0903 (6)	−0.0115 (4)	0.0457 (5)	−0.0095 (4)
N1	0.0532 (13)	0.0462 (13)	0.0320 (11)	0.0056 (10)	0.0192 (10)	0.0040 (9)
N2	0.0597 (14)	0.0440 (12)	0.0296 (11)	0.0123 (10)	0.0221 (11)	0.0046 (9)
O1	0.0890 (15)	0.0477 (11)	0.0363 (10)	0.0098 (10)	0.0336 (10)	0.0001 (8)
C1	0.0392 (14)	0.0470 (14)	0.0319 (13)	0.0031 (11)	0.0150 (11)	0.0036 (11)
C2	0.0406 (15)	0.0472 (15)	0.0359 (13)	0.0019 (12)	0.0098 (12)	−0.0017 (11)
C3	0.0454 (16)	0.0423 (14)	0.0488 (16)	0.0026 (12)	0.0146 (13)	0.0042 (12)
C4	0.0354 (14)	0.0539 (16)	0.0402 (14)	0.0002 (12)	0.0116 (12)	0.0112 (12)
C5	0.0448 (16)	0.0601 (18)	0.0333 (13)	−0.0106 (13)	0.0111 (12)	0.0018 (12)
C6	0.0513 (16)	0.0429 (14)	0.0354 (13)	−0.0045 (12)	0.0156 (12)	−0.0007 (11)
C7	0.0495 (16)	0.0469 (15)	0.0302 (13)	0.0044 (12)	0.0177 (12)	0.0002 (11)
C8	0.0527 (16)	0.0413 (14)	0.0368 (13)	0.0014 (12)	0.0244 (12)	0.0023 (11)
C9	0.0534 (16)	0.0450 (14)	0.0378 (14)	0.0112 (12)	0.0291 (13)	0.0059 (11)
C10	0.0623 (18)	0.0494 (16)	0.0565 (17)	0.0091 (13)	0.0401 (15)	0.0056 (13)
C11	0.089 (3)	0.0591 (19)	0.072 (2)	0.0241 (18)	0.052 (2)	0.0227 (17)
C12	0.093 (3)	0.093 (3)	0.058 (2)	0.045 (2)	0.045 (2)	0.029 (2)
C13	0.069 (2)	0.096 (3)	0.0420 (17)	0.0223 (19)	0.0210 (16)	−0.0035 (17)
C14	0.0590 (18)	0.076 (2)	0.0337 (14)	0.0234 (15)	0.0219 (14)	0.0061 (13)

Geometric parameters (Å, º) top

Cl1—C2	1.729 (3)	C5—C6	1.369 (4)
Cl2—C4	1.726 (3)	C5—H5	0.9300
Cl3—C10	1.714 (3)	C6—H6	0.9300
N1—C7	1.272 (3)	C7—H7	0.9300
N1—N2	1.380 (3)	C8—C9	1.497 (3)
N2—C8	1.341 (3)	C9—C10	1.383 (4)
N2—H2	0.893 (10)	C9—C14	1.420 (4)
O1—C8	1.225 (3)	C10—C11	1.391 (4)
C1—C2	1.391 (4)	C11—C12	1.364 (5)
C1—C6	1.396 (3)	C11—H11	0.9300
C1—C7	1.454 (3)	C12—C13	1.372 (5)
C2—C3	1.377 (3)	C12—H12	0.9300
C3—C4	1.378 (4)	C13—C14	1.384 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.373 (4)	C14—H14	0.9300

C7—N1—N2	114.9 (2)	N1—C7—H7	119.8
C8—N2—N1	119.05 (19)	C1—C7—H7	119.8
C8—N2—H2	123 (2)	O1—C8—N2	123.7 (2)
N1—N2—H2	118 (2)	O1—C8—C9	122.5 (2)
C2—C1—C6	116.7 (2)	N2—C8—C9	113.8 (2)
C2—C1—C7	121.8 (2)	C10—C9—C14	119.1 (2)
C6—C1—C7	121.5 (2)	C10—C9—C8	121.9 (2)
C3—C2—C1	122.3 (2)	C14—C9—C8	118.9 (2)
C3—C2—Cl1	117.5 (2)	C9—C10—C11	120.6 (3)
C1—C2—Cl1	120.12 (19)	C9—C10—Cl3	121.6 (2)
C2—C3—C4	118.6 (2)	C11—C10—Cl3	117.7 (2)
C2—C3—H3	120.7	C12—C11—C10	119.4 (3)
C4—C3—H3	120.7	C12—C11—H11	120.3
C5—C4—C3	121.1 (2)	C10—C11—H11	120.3
C5—C4—Cl2	120.4 (2)	C11—C12—C13	121.6 (3)
C3—C4—Cl2	118.4 (2)	C11—C12—H12	119.2
C6—C5—C4	119.3 (2)	C13—C12—H12	119.2
C6—C5—H5	120.4	C12—C13—C14	120.2 (3)
C4—C5—H5	120.4	C12—C13—H13	119.9
C5—C6—C1	122.0 (2)	C14—C13—H13	119.9
C5—C6—H6	119.0	C13—C14—C9	119.1 (3)
C1—C6—H6	119.0	C13—C14—H14	120.5
N1—C7—C1	120.4 (2)	C9—C14—H14	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.89 (1)	2.00 (1)	2.864 (3)	164 (3)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉Cl₃N₂O
M_r	327.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.4737 (11), 25.877 (4), 8.1833 (12)
β (°)	116.013 (2)
V (Å³)	1422.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.867, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	7752, 2828, 2066
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.121, 1.02
No. of reflections	2828
No. of parameters	184
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)	0.59, −0.36

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
N2—H2···O1ⁱ	0.893 (10)	1.995 (13)	2.864 (3)	164 (3)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors acknowledge support of this project by Hunan Provincial Natural Science Foundation of China Scientific Research (09JJ6022) and the Fund of Hunan Provincial Education Department (08B031), People's Republic of China.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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
Zhou, C.-S. & Yang, T. (2010). Acta Cryst. E66, o751. Web of Science CrossRef IUCr Journals Google Scholar