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

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ISSN: 2056-9890

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

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 ππ 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[Collison, S. R. & Fenton, D. E. (1996). Coord. Chem. Rev. 148, 19-40.]); Dong, He et al. (2007[Dong, W. K., He, X. N., Dong, C. M., Wang, L., Zhong, J. K., Chen, X. & Yu, T. Z. (2007). Z. Kristallogr. New Cryst. Struct. 222, 289-290.]); Dong, Duan et al. (2007[Dong, W. K., Duan, J. G., Dong, C. M., Ren, Z. L. & Shi, J. Y. (2007). Z. Kristallogr. New Cryst. Struct. 222, 327-328.]); Dong et al. (2008[Dong, W. K., Shi, J. Y., Zhong, J. K., Tian, Y. Q. & Duan, J. G. (2008). Chin. J. Inorg. Chem. 28, 10-14.]); Liu et al. (2008[Liu, G.-L., Chen, X., He, X.-N. & Dong, W.-K. (2008). Acta Cryst. E64, o659.]); Lu et al. (2006[Lu, Z. L., Yuan, M., Pan, F., Gao, S., Zhang, D. Q. & Zhu, D. B. (2006). Inorg. Chem. 45, 3538-3548.]); Mandal et al. (1996[Mandal, S. S., Kumar, N. V. & Varsheney, U. (1996). J. Inorg. Biochem. 63, 265-272.]); Shi et al. (2007[Shi, J., Dong, W., Zhang, Y. & Gao, S. (2007). Acta Cryst. E63, o4080.]); Yu et al. (2007[Yu, T. Z., Zhang, K., Zhao, Y. L., Yang, C. H., Zhang, H., Fan, D. W. & Dong, W. K. (2007). Inorg. Chem. Commun. 10, 401-403.], 2008[Yu, T. Z., Zhang, K., Zhao, Y. L., Yang, C. H., Zhang, H., Qian, L., Fan, D. W., Dong, W. K., Chen, L. L. & Qiu, Y. Q. (2008). Inorg. Chim. Acta, 361, 233-240.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18Cl2N2O2

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.841, Tmax = 0.953

  • 4304 measured reflections

  • 1531 independent reflections

  • 1310 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

Non-H atoms were refined anisotropically. H atoms were treated as riding atoms with distances C—H = 0.97 (CH2), 0.93 Å (CH), and Uiso(H) = 1.2 Ueq(C) and 1.5 Ueq(O).

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
[Figure 1] 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.
[Figure 2] 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
C18H18Cl2N2O2F(000) = 380
Mr = 365.24Dx = 1.351 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2364 reflections
a = 4.5296 (5) Åθ = 3.2–28.2°
b = 6.6231 (8) ŵ = 0.37 mm1
c = 29.963 (2) ÅT = 298 K
β = 92.526 (2)°Needle, colorless
V = 898.02 (16) Å30.48 × 0.28 × 0.13 mm
Z = 2
Data collection top
Bruker SMART 1000
diffractometer
1531 independent reflections
Radiation source: fine-focus sealed tube1310 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 55
Tmin = 0.841, Tmax = 0.953k = 75
4304 measured reflectionsl = 3534
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0452P)2 + 1.0643P]
where P = (Fo2 + 2Fc2)/3
1531 reflections(Δ/σ)max = 0.001
109 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C18H18Cl2N2O2V = 898.02 (16) Å3
Mr = 365.24Z = 2
Monoclinic, P21/nMo Kα radiation
a = 4.5296 (5) ŵ = 0.37 mm1
b = 6.6231 (8) ÅT = 298 K
c = 29.963 (2) Å0.48 × 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)
Tmin = 0.841, Tmax = 0.953Rint = 0.057
4304 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.10Δρmax = 0.21 e Å3
1531 reflectionsΔρmin = 0.29 e Å3
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
xyzUiso*/Ueq
Cl10.8257 (3)0.7688 (2)0.71001 (4)0.0939 (5)
N10.4408 (7)0.6370 (5)0.57897 (10)0.0570 (8)
O10.2543 (6)0.7961 (4)0.56512 (8)0.0607 (7)
C10.0979 (8)0.7356 (6)0.52466 (11)0.0598 (9)
H1A0.02730.62040.53040.072*
H1B0.23700.69680.50250.072*
C20.0885 (8)0.9111 (6)0.50759 (13)0.0643 (10)
H2A0.21600.86500.48280.077*
H2B0.21410.95510.53110.077*
C30.5650 (8)0.6708 (6)0.61688 (12)0.0570 (9)
H30.52330.78920.63210.068*
C40.7733 (7)0.5252 (5)0.63692 (11)0.0521 (8)
C50.9101 (8)0.5566 (6)0.67866 (12)0.0591 (9)
C61.1129 (9)0.4202 (7)0.69728 (13)0.0697 (11)
H61.20380.44540.72520.084*
C71.1776 (10)0.2505 (8)0.67465 (16)0.0820 (13)
H71.31330.15870.68710.098*
C81.0431 (11)0.2122 (7)0.63302 (16)0.0826 (13)
H81.08670.09460.61770.099*
C90.8444 (9)0.3496 (6)0.61452 (12)0.0636 (10)
H90.75620.32410.58650.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1045 (9)0.1019 (10)0.0731 (7)0.0144 (8)0.0213 (6)0.0275 (7)
N10.0621 (18)0.0562 (17)0.0522 (17)0.0094 (15)0.0026 (14)0.0042 (14)
O10.0694 (16)0.0559 (15)0.0555 (14)0.0125 (12)0.0105 (12)0.0013 (12)
C10.063 (2)0.064 (2)0.0514 (19)0.0040 (19)0.0059 (15)0.0049 (18)
C20.056 (2)0.075 (3)0.061 (2)0.0034 (19)0.0106 (17)0.018 (2)
C30.064 (2)0.057 (2)0.0498 (19)0.0071 (18)0.0003 (16)0.0012 (16)
C40.0524 (19)0.060 (2)0.0436 (17)0.0034 (17)0.0046 (14)0.0085 (16)
C50.059 (2)0.073 (2)0.0451 (18)0.0021 (19)0.0045 (15)0.0073 (18)
C60.061 (2)0.092 (3)0.055 (2)0.003 (2)0.0034 (17)0.020 (2)
C70.074 (3)0.089 (3)0.083 (3)0.022 (3)0.000 (2)0.033 (3)
C80.097 (3)0.071 (3)0.080 (3)0.030 (3)0.011 (2)0.013 (2)
C90.074 (2)0.069 (2)0.0483 (19)0.010 (2)0.0036 (17)0.0047 (18)
Geometric parameters (Å, º) top
Cl1—C51.742 (4)C3—H30.9300
N1—C31.265 (4)C4—C51.387 (5)
N1—O11.402 (4)C4—C91.387 (5)
O1—C11.434 (4)C5—C61.388 (5)
C1—C21.513 (5)C6—C71.351 (6)
C1—H1A0.9700C6—H60.9300
C1—H1B0.9700C7—C81.387 (7)
C2—C2i1.506 (8)C7—H70.9300
C2—H2A0.9700C8—C91.379 (5)
C2—H2B0.9700C8—H80.9300
C3—C41.460 (5)C9—H90.9300
C3—N1—O1111.8 (3)C5—C4—C3121.8 (3)
N1—O1—C1108.0 (3)C9—C4—C3121.0 (3)
O1—C1—C2108.6 (3)C4—C5—C6121.7 (4)
O1—C1—H1A110.0C4—C5—Cl1120.5 (3)
C2—C1—H1A110.0C6—C5—Cl1117.8 (3)
O1—C1—H1B110.0C7—C6—C5119.6 (4)
C2—C1—H1B110.0C7—C6—H6120.2
H1A—C1—H1B108.4C5—C6—H6120.2
C2i—C2—C1114.0 (4)C6—C7—C8120.4 (4)
C2i—C2—H2A108.8C6—C7—H7119.8
C1—C2—H2A108.8C8—C7—H7119.8
C2i—C2—H2B108.8C9—C8—C7119.6 (4)
C1—C2—H2B108.8C9—C8—H8120.2
H2A—C2—H2B107.7C7—C8—H8120.2
N1—C3—C4120.4 (3)C8—C9—C4121.3 (4)
N1—C3—H3119.8C8—C9—H9119.3
C4—C3—H3119.8C4—C9—H9119.3
C5—C4—C9117.3 (3)
C3—N1—O1—C1173.4 (3)C3—C4—C5—Cl12.6 (5)
N1—O1—C1—C2176.2 (3)C4—C5—C6—C70.9 (6)
O1—C1—C2—C2i66.7 (5)Cl1—C5—C6—C7178.0 (3)
O1—N1—C3—C4178.7 (3)C5—C6—C7—C80.1 (7)
N1—C3—C4—C5179.1 (4)C6—C7—C8—C90.7 (7)
N1—C3—C4—C91.5 (6)C7—C8—C9—C40.7 (7)
C9—C4—C5—C60.8 (5)C5—C4—C9—C80.1 (6)
C3—C4—C5—C6178.6 (3)C3—C4—C9—C8179.4 (4)
C9—C4—C5—Cl1178.0 (3)
Symmetry code: (i) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O1ii0.932.663.581 (5)171
Symmetry code: (ii) x+1, y1, z.

Experimental details

Crystal data
Chemical formulaC18H18Cl2N2O2
Mr365.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)4.5296 (5), 6.6231 (8), 29.963 (2)
β (°) 92.526 (2)
V3)898.02 (16)
Z2
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.48 × 0.28 × 0.13
Data collection
DiffractometerBruker SMART 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.841, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections
4304, 1531, 1310
Rint0.057
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.164, 1.10
No. of reflections1531
No. of parameters109
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C8—H8···O1i0.9302.6593.581 (5)171
Symmetry code: (i) x+1, y1, 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

First citationCollison, S. R. & Fenton, D. E. (1996). Coord. Chem. Rev. 148, 19–40.  Google Scholar
First citationDong, W. K., Duan, J. G., Dong, C. M., Ren, Z. L. & Shi, J. Y. (2007). Z. Kristallogr. New Cryst. Struct. 222, 327–328.  CAS Google Scholar
First citationDong, W. K., He, X. N., Dong, C. M., Wang, L., Zhong, J. K., Chen, X. & Yu, T. Z. (2007). Z. Kristallogr. New Cryst. Struct. 222, 289–290.  CAS Google Scholar
First citationDong, W. K., Shi, J. Y., Zhong, J. K., Tian, Y. Q. & Duan, J. G. (2008). Chin. J. Inorg. Chem. 28, 10–14.  Google Scholar
First citationLiu, G.-L., Chen, X., He, X.-N. & Dong, W.-K. (2008). Acta Cryst. E64, o659.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationMandal, S. S., Kumar, N. V. & Varsheney, U. (1996). J. Inorg. Biochem. 63, 265–272.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShi, J., Dong, W., Zhang, Y. & Gao, S. (2007). Acta Cryst. E63, o4080.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationYu, T. Z., Zhang, K., Zhao, Y. L., Yang, C. H., Zhang, H., Fan, D. W. & Dong, W. K. (2007). Inorg. Chem. Commun. 10, 401–403.  Web of Science CSD CrossRef CAS Google Scholar
First citationYu, T. Z., Zhang, K., Zhao, Y. L., Yang, C. H., Zhang, H., Qian, L., Fan, D. W., Dong, W. K., Chen, L. L. & Qiu, Y. Q. (2008). Inorg. Chim. Acta, 361, 233–240.  Web of Science CSD CrossRef CAS Google Scholar

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