(E)-Benzaldehyde (2,4,6-trichloro-phen-yl)hydrazone.

The title compound, C(13)H(9)Cl(3)N(2), was obtained from a condensation reaction of benzaldehyde and 2,4,6-trichloro-phenyl-hydrazine. The mol-ecule assumes an E configuration with the phenyl ring and trichloro-phenyl ring located on opposite sides of the C=N bond. The phenyl ring is oriented at a dihedral angle of 42.58 (12)° with respect to the tricholorophenyl ring. In the crystal, the mol-ecules are linked via N-H⋯N hydrogen bonds, forming supra-molecular chains running along the c axis. π-π stacking is present between parallel trichloro-phenyl rings of adjacent mol-ecules, the face-to-face and centroid-centroid distances being 3.369 (14) and 3.724 (2) Å, respectively.

Related literature

For the biological activity of phenyl­hydrazone derivatives, see: Okabe et al. (1993 ▶). For related structures, see: Shan et al. (2003 ▶); Fan et al. (2005 ▶); Bolte & Dill (1998 ▶).

Experimental

Crystal data

C13H9Cl3N2

M = 299.57

Monoclinic,

a = 13.913 (6) Å

b = 12.867 (5) Å

c = 7.652 (3) Å

β = 98.739 (5)°

V = 1353.9 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 295 K

0.36 × 0.30 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.86, T max = 0.92

11730 measured reflections

2436 independent reflections

1936 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.06

2436 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.32 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100328X/xu5149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100328X/xu5149Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H9Cl3N2	F(000) = 608
Mr = 299.57	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4171 reflections
a = 13.913 (6) Å	θ = 2.8–26.3°
b = 12.867 (5) Å	µ = 0.66 mm−1
c = 7.652 (3) Å	T = 295 K
β = 98.739 (5)°	Prism, colorless
V = 1353.9 (9) Å3	0.36 × 0.30 × 0.26 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2436 independent reflections
Radiation source: fine-focus sealed tube	1936 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.86, Tmax = 0.92	l = −9→9
11730 measured reflections

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) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.4002P] where P = (Fo2 + 2Fc2)/3
2436 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.82868 (5)	0.03185 (5)	0.52523 (10)	0.0786 (2)
Cl2	1.16441 (5)	0.21670 (7)	0.78646 (11)	0.0897 (3)
Cl3	0.85826 (6)	0.45120 (5)	0.53336 (10)	0.0877 (3)
N1	0.75114 (15)	0.24687 (17)	0.4714 (3)	0.0746 (6)
H1N	0.7271	0.1962	0.3849	0.089*
N2	0.69094 (13)	0.30372 (14)	0.5622 (2)	0.0566 (5)
C1	0.84849 (16)	0.24097 (18)	0.5442 (3)	0.0557 (6)
C2	0.89458 (15)	0.14534 (18)	0.5762 (3)	0.0548 (5)
C3	0.99117 (16)	0.13659 (19)	0.6484 (3)	0.0595 (6)
H3	1.0203	0.0717	0.6674	0.071*
C4	1.04329 (16)	0.2259 (2)	0.6915 (3)	0.0612 (6)
C5	1.00210 (17)	0.3222 (2)	0.6597 (3)	0.0638 (6)
H5	1.0386	0.3821	0.6883	0.077*
C6	0.90617 (18)	0.32876 (19)	0.5850 (3)	0.0603 (6)
C7	0.59985 (17)	0.29350 (17)	0.5147 (3)	0.0582 (6)
H7	0.5769	0.2464	0.4258	0.070*
C8	0.53090 (15)	0.35459 (18)	0.5976 (3)	0.0535 (5)
C9	0.56026 (17)	0.44135 (18)	0.6979 (3)	0.0561 (5)
H9	0.6254	0.4608	0.7146	0.067*
C10	0.4942 (2)	0.4996 (2)	0.7737 (3)	0.0760 (7)
H10	0.5151	0.5578	0.8411	0.091*
C11	0.3983 (2)	0.4720 (3)	0.7501 (4)	0.0934 (10)
H11	0.3539	0.5115	0.8011	0.112*
C12	0.3676 (2)	0.3869 (3)	0.6520 (5)	0.0952 (10)
H12	0.3022	0.3683	0.6369	0.114*
C13	0.43269 (18)	0.3272 (2)	0.5741 (4)	0.0758 (7)
H13	0.4110	0.2694	0.5066	0.091*

	U11	U22	U33	U12	U13	U23
Cl1	0.0633 (4)	0.0709 (4)	0.1004 (5)	−0.0018 (3)	0.0087 (4)	−0.0148 (3)
Cl2	0.0506 (4)	0.1110 (6)	0.1040 (6)	−0.0073 (3)	0.0007 (3)	0.0177 (4)
Cl3	0.0985 (5)	0.0642 (4)	0.0989 (5)	0.0182 (4)	0.0100 (4)	0.0040 (4)
N1	0.0620 (12)	0.0951 (16)	0.0601 (12)	0.0270 (11)	−0.0114 (10)	−0.0335 (11)
N2	0.0565 (11)	0.0629 (11)	0.0472 (10)	0.0140 (9)	−0.0023 (9)	−0.0060 (8)
C1	0.0581 (13)	0.0691 (15)	0.0397 (11)	0.0130 (11)	0.0065 (10)	−0.0078 (10)
C2	0.0520 (12)	0.0631 (14)	0.0509 (12)	0.0030 (10)	0.0124 (10)	−0.0055 (10)
C3	0.0505 (13)	0.0658 (14)	0.0639 (14)	0.0065 (11)	0.0144 (11)	0.0089 (11)
C4	0.0470 (12)	0.0816 (17)	0.0564 (13)	0.0007 (11)	0.0131 (11)	0.0108 (12)
C5	0.0634 (15)	0.0684 (15)	0.0606 (14)	−0.0047 (12)	0.0130 (12)	−0.0005 (12)
C6	0.0697 (15)	0.0612 (14)	0.0501 (12)	0.0092 (12)	0.0093 (11)	−0.0009 (11)
C7	0.0608 (14)	0.0596 (13)	0.0492 (12)	0.0031 (11)	−0.0081 (11)	−0.0046 (10)
C8	0.0478 (12)	0.0649 (14)	0.0455 (11)	0.0044 (10)	−0.0002 (9)	0.0120 (10)
C9	0.0554 (13)	0.0670 (14)	0.0447 (11)	0.0102 (11)	0.0039 (10)	0.0081 (11)
C10	0.0832 (19)	0.0897 (18)	0.0567 (15)	0.0249 (15)	0.0159 (14)	0.0066 (13)
C11	0.077 (2)	0.130 (3)	0.081 (2)	0.030 (2)	0.0352 (17)	0.023 (2)
C12	0.0486 (15)	0.136 (3)	0.104 (2)	0.0061 (17)	0.0195 (16)	0.042 (2)
C13	0.0581 (15)	0.0892 (19)	0.0758 (17)	−0.0089 (14)	−0.0034 (13)	0.0176 (14)

Cl1—C2	1.737 (2)	C5—H5	0.9300
Cl2—C4	1.735 (2)	C7—C8	1.458 (3)
Cl3—C6	1.733 (2)	C7—H7	0.9300
N1—N2	1.377 (3)	C8—C9	1.381 (3)
N1—C1	1.386 (3)	C8—C13	1.396 (3)
N1—H1N	0.9526	C9—C10	1.380 (3)
N2—C7	1.271 (3)	C9—H9	0.9300
C1—C2	1.392 (3)	C10—C11	1.367 (4)
C1—C6	1.393 (3)	C10—H10	0.9300
C2—C3	1.378 (3)	C11—C12	1.359 (5)
C3—C4	1.372 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.389 (4)
C4—C5	1.372 (3)	C12—H12	0.9300
C5—C6	1.372 (3)	C13—H13	0.9300
N2—N1—C1	117.26 (18)	N2—C7—C8	120.9 (2)
N2—N1—H1N	122.5	N2—C7—H7	119.6
C1—N1—H1N	117.4	C8—C7—H7	119.6
C7—N2—N1	117.19 (19)	C9—C8—C13	118.5 (2)
N1—C1—C2	121.0 (2)	C9—C8—C7	121.3 (2)
N1—C1—C6	122.7 (2)	C13—C8—C7	120.3 (2)
C2—C1—C6	116.3 (2)	C10—C9—C8	120.9 (2)
C3—C2—C1	122.5 (2)	C10—C9—H9	119.6
C3—C2—Cl1	118.09 (18)	C8—C9—H9	119.6
C1—C2—Cl1	119.38 (18)	C11—C10—C9	120.2 (3)
C4—C3—C2	118.4 (2)	C11—C10—H10	119.9
C4—C3—H3	120.8	C9—C10—H10	119.9
C2—C3—H3	120.8	C12—C11—C10	120.1 (3)
C3—C4—C5	121.5 (2)	C12—C11—H11	120.0
C3—C4—Cl2	119.22 (19)	C10—C11—H11	120.0
C5—C4—Cl2	119.3 (2)	C11—C12—C13	120.8 (3)
C4—C5—C6	118.9 (2)	C11—C12—H12	119.6
C4—C5—H5	120.6	C13—C12—H12	119.6
C6—C5—H5	120.6	C12—C13—C8	119.7 (3)
C5—C6—C1	122.3 (2)	C12—C13—H13	120.2
C5—C6—Cl3	117.8 (2)	C8—C13—H13	120.2
C1—C6—Cl3	119.84 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	0.95	2.44	3.183 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	0.95	2.44	3.183 (3)	134

Symmetry code: (i) .