(1E,2E)-1,2-Bis[1-(3-chloro-phen-yl)ethyl-idene]hydrazine.

The title mol-ecule, C(16)H(14)Cl(2)N(2), lies on an inversion center. The dihedral angle between the symmetry-related benzene rings is 0.02 (11)°. The mean plane of the central C(meth-yl)-C=N-N=C-C(meth-yl) unit forms a dihedral angle of 5.57 (12)° with the symmetry-unique benzene ring.

Related literature

For background to the biological activity and fluorescent properties of hydrazones, see: Li et al. (2009 ▶); n class="Gene">Qin et al. (2009 ▶). For related structures see: Chantrapromma et al. (2010 ▶); Fun et al. (2010 ▶, 2011 ▶); Jansrisewangwong et al. (2010 ▶); Nilwanna et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14Cl2N2

M = 305.19

Monoclinic,

a = 10.7796 (18) Å

b = 5.2725 (9) Å

c = 15.3427 (18) Å

β = 121.540 (8)°

V = 743.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.43 mm−1

T = 297 K

0.31 × 0.15 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.880, T max = 0.957

7616 measured reflections

1970 independent reflections

1469 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.180

S = 1.09

1970 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2009 ▶); 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, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049725/lh5380sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049725/lh5380Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049725/lh5380Isup3.cml

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

C16H14Cl2N2	F(000) = 316
Mr = 305.19	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Melting point = 356–358 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.7796 (18) Å	Cell parameters from 1970 reflections
b = 5.2725 (9) Å	θ = 2.2–29.0°
c = 15.3427 (18) Å	µ = 0.43 mm−1
β = 121.540 (8)°	T = 297 K
V = 743.2 (2) Å3	Block, yellow
Z = 2	0.31 × 0.15 × 0.11 mm

Bruker APEX DUO CCD area-detector diffractometer	1970 independent reflections
Radiation source: sealed tube	1469 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 29.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.880, Tmax = 0.957	k = −7→6
7616 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0951P)2 + 0.2508P] where P = (Fo2 + 2Fc2)/3
1970 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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	0.49474 (7)	0.23824 (14)	0.85934 (6)	0.0708 (3)
N1	0.0247 (2)	0.5365 (4)	0.96753 (14)	0.0543 (5)
C1	0.1907 (2)	0.4809 (4)	0.91400 (14)	0.0413 (4)
C2	0.3036 (2)	0.3431 (4)	0.91724 (16)	0.0460 (5)
H2A	0.3438	0.2045	0.9607	0.055*
C3	0.3550 (2)	0.4148 (4)	0.85517 (16)	0.0478 (5)
C4	0.2988 (2)	0.6198 (5)	0.78983 (17)	0.0527 (6)
H4A	0.3353	0.6655	0.7490	0.063*
C5	0.1869 (3)	0.7552 (4)	0.78659 (19)	0.0535 (6)
H5A	0.1476	0.8939	0.7430	0.064*
C6	0.1324 (2)	0.6875 (4)	0.84733 (16)	0.0468 (5)
H6A	0.0565	0.7801	0.8438	0.056*
C7	0.1350 (2)	0.4107 (4)	0.98120 (15)	0.0426 (4)
C8	0.2087 (3)	0.2056 (6)	1.0585 (2)	0.0711 (8)
H8A	0.1613	0.1850	1.0964	0.107*
H8B	0.3088	0.2501	1.1045	0.107*
H8C	0.2034	0.0496	1.0245	0.107*

	U11	U22	U33	U12	U13	U23
Cl1	0.0653 (4)	0.0831 (5)	0.0902 (5)	0.0089 (3)	0.0590 (4)	−0.0068 (3)
N1	0.0601 (11)	0.0663 (12)	0.0567 (10)	0.0214 (9)	0.0445 (9)	0.0206 (9)
C1	0.0438 (10)	0.0463 (10)	0.0414 (9)	0.0004 (8)	0.0276 (8)	−0.0015 (8)
C2	0.0470 (10)	0.0503 (11)	0.0487 (10)	0.0038 (9)	0.0306 (9)	−0.0020 (9)
C3	0.0459 (10)	0.0571 (13)	0.0518 (11)	−0.0052 (9)	0.0335 (9)	−0.0125 (9)
C4	0.0611 (13)	0.0609 (14)	0.0530 (11)	−0.0129 (11)	0.0415 (11)	−0.0081 (10)
C5	0.0604 (13)	0.0577 (14)	0.0507 (12)	0.0002 (10)	0.0347 (11)	0.0068 (9)
C6	0.0466 (10)	0.0547 (12)	0.0473 (10)	0.0046 (9)	0.0302 (9)	0.0048 (9)
C7	0.0471 (10)	0.0470 (11)	0.0435 (9)	0.0054 (8)	0.0305 (8)	0.0023 (8)
C8	0.0766 (17)	0.0858 (19)	0.0761 (16)	0.0374 (15)	0.0574 (15)	0.0370 (15)

Cl1—C3	1.743 (2)	C4—C5	1.380 (3)
N1—C7	1.279 (3)	C4—H4A	0.9300
N1—N1i	1.406 (3)	C5—C6	1.383 (3)
C1—C2	1.395 (3)	C5—H5A	0.9300
C1—C6	1.399 (3)	C6—H6A	0.9300
C1—C7	1.486 (3)	C7—C8	1.491 (3)
C2—C3	1.382 (3)	C8—H8A	0.9600
C2—H2A	0.9300	C8—H8B	0.9600
C3—C4	1.380 (3)	C8—H8C	0.9600
C7—N1—N1i	113.9 (2)	C4—C5—H5A	119.6
C2—C1—C6	118.78 (18)	C6—C5—H5A	119.6
C2—C1—C7	120.47 (19)	C5—C6—C1	120.5 (2)
C6—C1—C7	120.74 (18)	C5—C6—H6A	119.8
C3—C2—C1	119.3 (2)	C1—C6—H6A	119.8
C3—C2—H2A	120.3	N1—C7—C1	115.82 (18)
C1—C2—H2A	120.3	N1—C7—C8	124.68 (19)
C4—C3—C2	122.2 (2)	C1—C7—C8	119.49 (18)
C4—C3—Cl1	119.20 (16)	C7—C8—H8A	109.5
C2—C3—Cl1	118.63 (18)	C7—C8—H8B	109.5
C5—C4—C3	118.4 (2)	H8A—C8—H8B	109.5
C5—C4—H4A	120.8	C7—C8—H8C	109.5
C3—C4—H4A	120.8	H8A—C8—H8C	109.5
C4—C5—C6	120.9 (2)	H8B—C8—H8C	109.5
C6—C1—C2—C3	0.3 (3)	C2—C1—C6—C5	−0.6 (3)
C7—C1—C2—C3	−178.95 (19)	C7—C1—C6—C5	178.6 (2)
C1—C2—C3—C4	0.2 (3)	N1i—N1—C7—C1	179.8 (2)
C1—C2—C3—Cl1	−179.32 (16)	N1i—N1—C7—C8	−0.5 (4)
C2—C3—C4—C5	−0.4 (3)	C2—C1—C7—N1	−175.2 (2)
Cl1—C3—C4—C5	179.15 (17)	C6—C1—C7—N1	5.6 (3)
C3—C4—C5—C6	0.0 (4)	C2—C1—C7—C8	5.1 (3)
C4—C5—C6—C1	0.5 (4)	C6—C1—C7—C8	−174.1 (2)