2,2'-Dichloro-1,1'-[(butane-1,4-diyldi-oxy)bis-(nitrilo-methyl-idyne)]dibenzene.

The mol-ecule of the title compound, C(18)H(18)Cl(2)N(2)O(2), lies across a crystallographic inversion centre and adopts an E configuration with respect to the azomethine C=N bond. The imino group is coplanar with the aromatic ring. Within the mol-ecule, the planar units are parallel, but extend in opposite directions from the dimethyl-ene bridge. In the crystal structure, the title compound exhibits a layer packing structure via weak π-π stacking inter-actions [inter-molecular plane-to-plane distances between adjacent aromatic rings are 3.461 (3) Å]. Mol-ecules in each layer are linked by inter-molecular C-H⋯O hydrogen-bonding inter-actions.

Related literature

For related literature, see: Collison & Fenton (1996 ▶); Dong, He et al. (2007 ▶); Dong, Duan et al. (2007 ▶); Dong et al. (2008 ▶); Liu et al. (2008 ▶); Lu et al. (2006 ▶); Mandal et al. (1996 ▶); Shi et al. (2007 ▶); Yu et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C18H18Cl2N2O2

M = 365.24

Monoclinic,

a = 4.5296 (5) Å

b = 6.6231 (8) Å

c = 29.963 (2) Å

β = 92.526 (2)°

V = 898.02 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 298 (2) K

0.48 × 0.28 × 0.13 mm

Data collection

Bruker SMART 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.841, T max = 0.953

4304 measured reflections

1531 independent reflections

1310 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.164

S = 1.10

1531 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024355/om2252sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024355/om2252Isup2.hkl

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

C18H18Cl2N2O2	F000 = 380
Mr = 365.24	Dx = 1.351 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2364 reflections
a = 4.5296 (5) Å	θ = 3.2–28.2º
b = 6.6231 (8) Å	µ = 0.37 mm−1
c = 29.963 (2) Å	T = 298 (2) K
β = 92.526 (2)º	Needle, colorless
V = 898.02 (16) Å3	0.48 × 0.28 × 0.13 mm
Z = 2

Bruker SMART 1000 diffractometer	1531 independent reflections
Radiation source: fine-focus sealed tube	1310 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.841, Tmax = 0.953	k = −7→5
4304 measured reflections	l = −35→34

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074	H-atom parameters constrained
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.0452P)2 + 1.0643P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
1531 reflections	Δρmax = 0.21 e Å−3
109 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.8257 (3)	0.7688 (2)	0.71001 (4)	0.0939 (5)
N1	0.4408 (7)	0.6370 (5)	0.57897 (10)	0.0570 (8)
O1	0.2543 (6)	0.7961 (4)	0.56512 (8)	0.0607 (7)
C1	0.0979 (8)	0.7356 (6)	0.52466 (11)	0.0598 (9)
H1A	−0.0273	0.6204	0.5304	0.072*
H1B	0.2370	0.6968	0.5025	0.072*
C2	−0.0885 (8)	0.9111 (6)	0.50759 (13)	0.0643 (10)
H2A	−0.2160	0.8650	0.4828	0.077*
H2B	−0.2141	0.9551	0.5311	0.077*
C3	0.5650 (8)	0.6708 (6)	0.61688 (12)	0.0570 (9)
H3	0.5233	0.7892	0.6321	0.068*
C4	0.7733 (7)	0.5252 (5)	0.63692 (11)	0.0521 (8)
C5	0.9101 (8)	0.5566 (6)	0.67866 (12)	0.0591 (9)
C6	1.1129 (9)	0.4202 (7)	0.69728 (13)	0.0697 (11)
H6	1.2038	0.4454	0.7252	0.084*
C7	1.1776 (10)	0.2505 (8)	0.67465 (16)	0.0820 (13)
H7	1.3133	0.1587	0.6871	0.098*
C8	1.0431 (11)	0.2122 (7)	0.63302 (16)	0.0826 (13)
H8	1.0867	0.0946	0.6177	0.099*
C9	0.8444 (9)	0.3496 (6)	0.61452 (12)	0.0636 (10)
H9	0.7562	0.3241	0.5865	0.076*

	U11	U22	U33	U12	U13	U23
Cl1	0.1045 (9)	0.1019 (10)	0.0731 (7)	0.0144 (8)	−0.0213 (6)	−0.0275 (7)
N1	0.0621 (18)	0.0562 (17)	0.0522 (17)	0.0094 (15)	−0.0026 (14)	0.0042 (14)
O1	0.0694 (16)	0.0559 (15)	0.0555 (14)	0.0125 (12)	−0.0105 (12)	−0.0013 (12)
C1	0.063 (2)	0.064 (2)	0.0514 (19)	−0.0040 (19)	−0.0059 (15)	0.0049 (18)
C2	0.056 (2)	0.075 (3)	0.061 (2)	−0.0034 (19)	−0.0106 (17)	0.018 (2)
C3	0.064 (2)	0.057 (2)	0.0498 (19)	0.0071 (18)	−0.0003 (16)	−0.0012 (16)
C4	0.0524 (19)	0.060 (2)	0.0436 (17)	0.0034 (17)	0.0046 (14)	0.0085 (16)
C5	0.059 (2)	0.073 (2)	0.0451 (18)	−0.0021 (19)	0.0045 (15)	0.0073 (18)
C6	0.061 (2)	0.092 (3)	0.055 (2)	0.003 (2)	−0.0034 (17)	0.020 (2)
C7	0.074 (3)	0.089 (3)	0.083 (3)	0.022 (3)	0.000 (2)	0.033 (3)
C8	0.097 (3)	0.071 (3)	0.080 (3)	0.030 (3)	0.011 (2)	0.013 (2)
C9	0.074 (2)	0.069 (2)	0.0483 (19)	0.010 (2)	0.0036 (17)	0.0047 (18)

Cl1—C5	1.742 (4)	C3—H3	0.9300
N1—C3	1.265 (4)	C4—C5	1.387 (5)
N1—O1	1.402 (4)	C4—C9	1.387 (5)
O1—C1	1.434 (4)	C5—C6	1.388 (5)
C1—C2	1.513 (5)	C6—C7	1.351 (6)
C1—H1A	0.9700	C6—H6	0.9300
C1—H1B	0.9700	C7—C8	1.387 (7)
C2—C2i	1.506 (8)	C7—H7	0.9300
C2—H2A	0.9700	C8—C9	1.379 (5)
C2—H2B	0.9700	C8—H8	0.9300
C3—C4	1.460 (5)	C9—H9	0.9300
C3—N1—O1	111.8 (3)	C5—C4—C3	121.8 (3)
N1—O1—C1	108.0 (3)	C9—C4—C3	121.0 (3)
O1—C1—C2	108.6 (3)	C4—C5—C6	121.7 (4)
O1—C1—H1A	110.0	C4—C5—Cl1	120.5 (3)
C2—C1—H1A	110.0	C6—C5—Cl1	117.8 (3)
O1—C1—H1B	110.0	C7—C6—C5	119.6 (4)
C2—C1—H1B	110.0	C7—C6—H6	120.2
H1A—C1—H1B	108.4	C5—C6—H6	120.2
C2i—C2—C1	114.0 (4)	C6—C7—C8	120.4 (4)
C2i—C2—H2A	108.8	C6—C7—H7	119.8
C1—C2—H2A	108.8	C8—C7—H7	119.8
C2i—C2—H2B	108.8	C9—C8—C7	119.6 (4)
C1—C2—H2B	108.8	C9—C8—H8	120.2
H2A—C2—H2B	107.7	C7—C8—H8	120.2
N1—C3—C4	120.4 (3)	C8—C9—C4	121.3 (4)
N1—C3—H3	119.8	C8—C9—H9	119.3
C4—C3—H3	119.8	C4—C9—H9	119.3
C5—C4—C9	117.3 (3)
C3—N1—O1—C1	−173.4 (3)	C3—C4—C5—Cl1	2.6 (5)
N1—O1—C1—C2	−176.2 (3)	C4—C5—C6—C7	−0.9 (6)
O1—C1—C2—C2i	66.7 (5)	Cl1—C5—C6—C7	178.0 (3)
O1—N1—C3—C4	−178.7 (3)	C5—C6—C7—C8	0.1 (7)
N1—C3—C4—C5	−179.1 (4)	C6—C7—C8—C9	0.7 (7)
N1—C3—C4—C9	1.5 (6)	C7—C8—C9—C4	−0.7 (7)
C9—C4—C5—C6	0.8 (5)	C5—C4—C9—C8	−0.1 (6)
C3—C4—C5—C6	−178.6 (3)	C3—C4—C9—C8	179.4 (4)
C9—C4—C5—Cl1	−178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ii	0.93	2.66	3.581 (5)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.66	3.581 (5)	171

Symmetry code: (i) .