N,N'-Bis(3,5-dichloro-benzyl-idene)-ethane-1,2-diamine.

The mol-ecule of the title Schiff base compound, C(16)H(12)Cl(4)N(2), lies across an inversion centre and adopts an E configuration with respect to the azomethine C=N bond. The imine groups are coplanar with the aromatic rings. Within the mol-ecule, the planar units are parallel but extend in opposite directions from the dimethyl-ene bridge. In the crystal structure, mol-ecules are linked together by inter-molecular C-H⋯Cl hydrogen bonds along the a axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun & Kia (2008a ▶,b ▶,c ▶); Fun, Kargar & Kia (2008 ▶); Fun, Kia & Kargar (2008 ▶). For information on Schiff base complexes and their applications, see, for example: Pal et al. (2005 ▶); Calligaris & Randaccio (1987 ▶); Hou et al. (2001 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C16H12Cl4N2

M = 374.08

Monoclinic,

a = 8.0539 (3) Å

b = 14.0170 (4) Å

c = 7.5015 (3) Å

β = 110.612 (1)°

V = 792.64 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.74 mm−1

T = 100.0 (1) K

0.52 × 0.25 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.699, T max = 0.908

34536 measured reflections

4162 independent reflections

3485 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.06

4162 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033588/bg2206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033588/bg2206Isup2.hkl

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

C16H12Cl4N2	F(000) = 380
Mr = 374.08	Dx = 1.567 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9889 reflections
a = 8.0539 (3) Å	θ = 2.7–39.9°
b = 14.0170 (4) Å	µ = 0.74 mm−1
c = 7.5015 (3) Å	T = 100 K
β = 110.612 (1)°	Block, colourless
V = 792.64 (5) Å3	0.52 × 0.25 × 0.13 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	4162 independent reflections
Radiation source: fine-focus sealed tube	3485 reflections with I > 2σ(I)
graphite	Rint = 0.035
CCD rotation images, thin slices scans	θmax = 37.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.699, Tmax = 0.908	k = −23→24
34536 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: refall
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1408P] where P = (Fo2 + 2Fc2)/3
4162 reflections	(Δ/σ)max = 0.001
124 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	Uiso*/Ueq
Cl1	0.28013 (3)	0.291680 (16)	−0.02974 (3)	0.02218 (6)
Cl2	0.72672 (3)	0.547370 (15)	0.42924 (4)	0.02557 (7)
N1	0.83741 (10)	0.09945 (5)	0.45102 (12)	0.01963 (14)
C1	0.58794 (11)	0.24294 (6)	0.24399 (13)	0.01689 (14)
C2	0.47672 (11)	0.31735 (6)	0.15494 (13)	0.01727 (14)
C3	0.51579 (12)	0.41204 (6)	0.20925 (13)	0.01900 (15)
C4	0.67376 (12)	0.43026 (6)	0.35795 (13)	0.01858 (14)
C5	0.78922 (11)	0.35774 (6)	0.45130 (13)	0.01811 (14)
C6	0.74533 (11)	0.26360 (6)	0.39426 (12)	0.01621 (13)
C7	0.86553 (11)	0.18627 (6)	0.49751 (12)	0.01690 (14)
C8	0.96808 (13)	0.03109 (6)	0.56502 (14)	0.02076 (16)
H1	0.558 (2)	0.1783 (10)	0.202 (2)	0.025 (4)*
H3	0.447 (2)	0.4639 (12)	0.150 (2)	0.034 (4)*
H5	0.8978 (18)	0.3723 (10)	0.5610 (19)	0.019 (3)*
H7	0.956 (2)	0.2083 (11)	0.602 (2)	0.027 (4)*
H8A	0.9095 (19)	−0.0120 (10)	0.641 (2)	0.019 (3)*
H8B	1.071 (2)	0.0617 (11)	0.660 (2)	0.022 (3)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01762 (9)	0.02168 (10)	0.02490 (11)	0.00313 (6)	0.00456 (8)	0.00146 (7)
Cl2	0.02981 (12)	0.01319 (9)	0.03115 (12)	0.00056 (7)	0.00756 (9)	−0.00046 (7)
N1	0.0189 (3)	0.0151 (3)	0.0234 (3)	0.0039 (2)	0.0056 (3)	0.0025 (2)
C1	0.0164 (3)	0.0142 (3)	0.0213 (3)	0.0015 (2)	0.0082 (3)	0.0015 (2)
C2	0.0160 (3)	0.0164 (3)	0.0203 (3)	0.0021 (2)	0.0075 (3)	0.0019 (3)
C3	0.0200 (3)	0.0151 (3)	0.0234 (4)	0.0038 (3)	0.0096 (3)	0.0030 (3)
C4	0.0211 (3)	0.0127 (3)	0.0234 (4)	0.0011 (3)	0.0098 (3)	0.0010 (3)
C5	0.0192 (3)	0.0148 (3)	0.0209 (3)	0.0013 (2)	0.0078 (3)	0.0011 (2)
C6	0.0167 (3)	0.0134 (3)	0.0200 (3)	0.0021 (2)	0.0083 (3)	0.0025 (2)
C7	0.0156 (3)	0.0160 (3)	0.0193 (3)	0.0031 (2)	0.0064 (3)	0.0018 (2)
C8	0.0218 (4)	0.0162 (3)	0.0227 (4)	0.0051 (3)	0.0058 (3)	0.0030 (3)

Cl1—C2	1.7353 (9)	C3—H3	0.929 (17)
Cl2—C4	1.7326 (9)	C4—C5	1.3893 (12)
N1—C7	1.2643 (11)	C5—C6	1.3939 (12)
N1—C8	1.4571 (11)	C5—H5	0.988 (13)
C1—C2	1.3839 (11)	C6—C7	1.4778 (11)
C1—C6	1.3983 (12)	C7—H7	0.916 (16)
C1—H1	0.962 (14)	C8—C8i	1.526 (2)
C2—C3	1.3916 (12)	C8—H8A	1.050 (15)
C3—C4	1.3888 (13)	C8—H8B	0.979 (15)
C7—N1—C8	116.67 (8)	C4—C5—H5	120.5 (8)
C2—C1—C6	118.82 (8)	C6—C5—H5	120.4 (8)
C2—C1—H1	120.4 (9)	C5—C6—C1	120.23 (7)
C6—C1—H1	120.8 (9)	C5—C6—C7	119.01 (7)
C1—C2—C3	122.43 (8)	C1—C6—C7	120.75 (7)
C1—C2—Cl1	118.86 (7)	N1—C7—C6	122.74 (8)
C3—C2—Cl1	118.70 (6)	N1—C7—H7	124.9 (10)
C4—C3—C2	117.34 (8)	C6—C7—H7	112.3 (10)
C4—C3—H3	117.8 (11)	N1—C8—C8i	109.68 (10)
C2—C3—H3	124.8 (11)	N1—C8—H8A	109.1 (8)
C3—C4—C5	122.12 (8)	C8i—C8—H8A	109.6 (8)
C3—C4—Cl2	118.59 (6)	N1—C8—H8B	112.8 (9)
C5—C4—Cl2	119.29 (7)	C8i—C8—H8B	109.2 (9)
C4—C5—C6	119.05 (8)	H8A—C8—H8B	106.4 (12)
C6—C1—C2—C3	0.08 (14)	C4—C5—C6—C1	0.58 (14)
C6—C1—C2—Cl1	−179.26 (7)	C4—C5—C6—C7	−178.13 (8)
C1—C2—C3—C4	0.42 (14)	C2—C1—C6—C5	−0.59 (14)
Cl1—C2—C3—C4	179.76 (7)	C2—C1—C6—C7	178.10 (8)
C2—C3—C4—C5	−0.43 (14)	C8—N1—C7—C6	179.56 (8)
C2—C3—C4—Cl2	179.97 (7)	C5—C6—C7—N1	−177.99 (9)
C3—C4—C5—C6	−0.06 (14)	C1—C6—C7—N1	3.30 (14)
Cl2—C4—C5—C6	179.54 (7)	C7—N1—C8—C8i	−127.06 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2ii	0.962 (14)	2.830 (16)	3.6479 (9)	143.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl2i	0.962 (14)	2.830 (16)	3.6479 (9)	143.5 (13)

Symmetry code: (i) .