1,4-Dichloro-2,3-bis­(chloro­meth­yl)butane

Cordes, D.B.; Aitken, K.M.; Aitken, R.A.

doi:10.1107/S1600536812048398

Volume 68
Part 12
Page o3495
December 2012

Received 21 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.002 Å
R = 0.030
wR = 0.075
Data-to-parameter ratio = 18.2
Details

1,4-Dichloro-2,3-bis(chloromethyl)butane

David B. Cordes,^a ⁺ Kati M. Aitken ^a and R. Alan Aitken ^a ^*

^aEaStCHEM School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
Correspondence e-mail: raa@st-andrews.ac.uk

The title compound, C₆H₁₀Cl₄, adopts a geometric arrangement with two C-Cl bonds antiperiplanar to C-H bonds and the other two antiperiplanar to C-C bonds. While minimising steric replusion, this arrangement still gives rise to some intramolecular C-HCl contacts. In the crystal, molecules are connected into a three-dimensional architecture via further C-HCl contacts.

Related literature

The title compound was previously prepared by Weinges & Spänig (1968). For related structures of polychlorinated acylic alkanes, see: Frenzen et al. (1999); Frenzen & Coelhan (1998); Bart et al. (1979, 1980); Karapetyan et al. (2008); Kabalka et al. (2005); Podsiadlo & Katrusiak (2006); Klaeboe et al. (1986).

Experimental

Crystal data

C₆H₁₀Cl₄
M_r = 223.94
Orthorhombic, P b c a
a = 8.998 (3) Å
b = 8.400 (3) Å
c = 24.643 (7) Å
V = 1862.6 (10) Å³
Z = 8
Mo K radiation
= 1.20 mm^-1
T = 93 K
0.25 × 0.25 × 0.10 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) T_min = 0.746, T_max = 1.000
8405 measured reflections
1658 independent reflections
1553 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.075
S = 1.12
1658 reflections
91 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1BCl3	0.99	2.76	3.2097 (19)	108
C4-H4BCl4	0.99	2.80	3.2445 (19)	108
C5-H5BCl1	0.99	2.74	3.2069 (19)	109
C6-H6BCl2	0.99	2.72	3.1940 (18)	110
C2-H2Cl3ⁱ	1.00	2.93	3.8599 (19)	155
C3-H3Cl2ⁱⁱ	1.00	2.86	3.8092 (19)	160
C4-H4BCl3ⁱ	0.99	2.92	3.657 (2)	132
C5-H5ACl2ⁱⁱⁱ	0.99	2.90	3.6951 (19)	138
C6-H6ACl1^iv	0.99	2.84	3.655 (2)	140
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) -x, -y, -z.

Data collection: CrystalClear (Rigaku, 2010); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5174 ).

Acknowledgements

The authors are grateful to the University of St Andrews and the Engineering and Physical Sciences Research Council (EPSRC, UK) for financial support.

References

Bart, J. C. J., Bassi, I. W. & Calcaterra, M. (1979). Acta Cryst. B35, 2646-2650.
Bart, J. C. J., Bassi, I. W. & Calcaterra, M. (1980). Acta Cryst. B36, 421-424.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Frenzen, G. & Coelhan, M. (1998). Private communication (refcode HITZOZ). CCDC, Cambridge, England.
Frenzen, G., Sippel, H. & Coelhan, M. (1999). Acta Cryst. C55, IUC9800079.
Kabalka, G. W., Wu, Z., Ju, Y. & Yao, M.-L. (2005). J. Org. Chem. 70, 10285-10291.
Karapetyan, A. A., Tamazyan, R. A., Mikaelyan, A. R., Grigoryan, A. M., Vardanyan, A. S. & Nikogosyan, L. Zh. (2008). J. Struct. Chem. 49, 965-968.
Klaeboe, P., Klewe, B., Martinsen, K., Nielsen, C. J., Powell, D. L. & Stubbles, D. J. (1986). J. Mol. Struct. 140, 1-18.
Podsiadlo, M. & Katrusiak, A. (2006). Acta Cryst. B62, 1071-1077.
Rigaku (2010). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Weinges, K. & Spänig, R. (1968). Chem. Ber. 101, 3010-3017.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds