2,2′-Dichloro-1,1′-[(butane-1,4-diyldi­oxy)bis­(nitrilo­methyl­idyne)]dibenzene

Ren, Z.-L.; Dong, W.-K.; Bai, W.-J.; He, X.-N.; Wang, L.

doi:10.1107/S1600536808024355

organic compounds

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Volume 64| Part 9| September 2008| Page o1678

doi:10.1107/S1600536808024355

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2,2′-Dichloro-1,1′-[(butane-1,4-diyldioxy)bis(nitrilomethylidyne)]dibenzene

Zong-Li Ren,^a Wen-Kui Dong,^a ^* Wen-Juan Bai,^a Xue-Ni He ^a and Li Wang ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 10 July 2008; accepted 30 July 2008; online 6 August 2008)

The molecule of the title compound, C₁₈H₁₈Cl₂N₂O₂, 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 molecule, the planar units are parallel, but extend in opposite directions from the dimethylene bridge. In the crystal structure, the title compound exhibits a layer packing structure via weak π–π stacking interactions [intermolecular plane-to-plane distances between adjacent aromatic rings are 3.461 (3) Å]. Molecules in each layer are linked by intermolecular C—H⋯O hydrogen-bonding interactions.

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_r = 365.24
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.074
wR(F²) = 0.164
S = 1.10
1531 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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) x+1, y-1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Schiff bases are an important class of compounds which can be used in a variety of studies such as organic synthesis, catalyst, drug design, material science and life science and so on (Collison, et al., 1996; Mandal, et al., 1996). In the past decades, a continuing attention has been drawn to the Schiff bases derived from benzaldehyde or salicylaldehyde and their metal complexes for the investigation of luminescent properties which could be finely tuned by different substituent groups bonded to the phenolic ring (Lu et al., 2006; Yu et al., 2007; Yu et al., 2008). Here, in continuation of our previous studies (Dong, Duan et al., 2007; Shi, et al., 2007), we report the synthesis and X-ray structure of a new Schiff base bisoxime compound 2,2'-dichloro-1,1'-[butane-1,4-diyldioxybis(nitrilomethylidyne)]dibenzene.

The crystal structure of the title compound is built up by only the C₁₈H₁₈Cl₂N₂O₂ molecules, in which all bond lengths are in normal ranges. The molecule, as shown in Fig. 1, lies across a crystallographic inversion centre (symmetry code: -x, -y, -z) and adopts an E configuration with respect to the azomethine C=N bond. The imino group is coplanar with the aromatic ring. Within the molecule, the planar units are parallel, with the distance 1.480 (4) Å [intra-molecular plane-to-plane distance], but extend in opposite directions from the dimethylene bridge. In the crystal structure, (Fig. 2) the title compound exhibits a layer packing structure via weak π-π stacking interactions [inter-molecular plane-to-plane distances between adjacent aromatic rings is 3.461 (3) Å]. Molecules in each layer are linked by intermolecular C8—H8···O1 hydrogen bonding interactions [C8···O1, 3.581 (5) Å].

Related literature top

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 top

2,2'-Dichloro-1,1'-[butane-1,4-diyldioxybis(nitrilomethylidyne)]dibenzene was synthesized according to an analogous method reported earlier (Dong, He et al., 2007; Dong, et al., 2008; Liu, et al., 2008). To an ethanol solution (3 ml) of 2-chloro-benzaldehyde (281.1 mg, 2.00 mmol) was added an ethanol solution (2 ml) of 1, 4-bis(aminooxy)butane (120.2 mg, 1.00 mmol). The mixture solution was stirred at 328 K for 4 h. When cooled to room temperature, the precipitate was filtered, and washed successively with ethanol and hexane, respectively. The product was dried under vacuum and purified with recrystallization from ethanol to yield 219.8 mg of the title compound. Yield, 60.1%. mp. 334–335 K. Anal. Calc. for C₁₈H₁₈Cl₂N₂O₂: C, 59.19; H, 4.97; N, 7.67. Found: C, 59.22; H, 5.03; N, 7.58.

Colorless needle-shaped single crystals suitable for X-ray diffraction studies were obtained after several weeks by slow evaporation from an ethyl-acetate/acetone mixed solution of the title compound.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom numbering scheme [Symmetry codes: -x, -y + 2, -z + 1]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. The packing diagram of the title compound showing intermolecular hydrogen bonds and π-π stacking interactions.

2,2'-Dichloro-1,1'-[(butane-1,4-diyldioxy)bis(nitrilomethylidyne)]dibenzene top

Crystal data top

C₁₈H₁₈Cl₂N₂O₂	F(000) = 380
M_r = 365.24	D_x = 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 = 3.2–28.2°
b = 6.6231 (8) Å	µ = 0.37 mm⁻¹
c = 29.963 (2) Å	T = 298 K
β = 92.526 (2)°	Needle, colorless
V = 898.02 (16) Å³	0.48 × 0.28 × 0.13 mm
Z = 2

Data collection top

Bruker SMART 1000 diffractometer	1531 independent reflections
Radiation source: fine-focus sealed tube	1310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
T_min = 0.841, T_max = 0.953	k = −7→5
4304 measured reflections	l = −35→34

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0452P)² + 1.0643P] where P = (F_o² + 2F_c²)/3
1531 reflections	(Δ/σ)_max = 0.001
109 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₈H₁₈Cl₂N₂O₂	V = 898.02 (16) Å³
M_r = 365.24	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.5296 (5) Å	µ = 0.37 mm⁻¹
b = 6.6231 (8) Å	T = 298 K
c = 29.963 (2) Å	0.48 × 0.28 × 0.13 mm
β = 92.526 (2)°

Data collection top

Bruker SMART 1000 diffractometer	1531 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1310 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.953	R_int = 0.057
4304 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.10	Δρ_max = 0.21 e Å⁻³
1531 reflections	Δρ_min = −0.29 e Å⁻³
109 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈Cl₂N₂O₂
M_r	365.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	4.5296 (5), 6.6231 (8), 29.963 (2)
β (°)	92.526 (2)
V (Å³)	898.02 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.48 × 0.28 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.841, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	4304, 1531, 1310
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.164, 1.10
No. of reflections	1531
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.29

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.930	2.659	3.581 (5)	171

Symmetry code: (i) x+1, y−1, z.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604–01) and the `Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03–01 A), which are gratefully acknowledged.

References

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1678

doi:10.1107/S1600536808024355

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-Di­chloro-1,1′-[(butane-1,4-diyldi­­oxy)bis­­(nitrilo­methyl­­idyne)]di­benzene

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-Dichloro-1,1′-[(butane-1,4-diyldioxy)bis(nitrilomethylidyne)]dibenzene