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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 [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.075
Data-to-parameter ratio = 18.2
Details
Open access

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

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-H...Cl contacts. In the crystal, molecules are connected into a three-dimensional architecture via further C-H...Cl contacts.

Related literature

The title compound was previously prepared by Weinges & Spänig (1968[Weinges, K. & Spänig, R. (1968). Chem. Ber. 101, 3010-3017.]). For related structures of polychlorinated acylic alkanes, see: Frenzen et al. (1999[Frenzen, G., Sippel, H. & Coelhan, M. (1999). Acta Cryst. C55, IUC9800079.]); Frenzen & Coelhan (1998[Frenzen, G. & Coelhan, M. (1998). Private communication (refcode HITZOZ). CCDC, Cambridge, England.]); Bart et al. (1979[Bart, J. C. J., Bassi, I. W. & Calcaterra, M. (1979). Acta Cryst. B35, 2646-2650.], 1980[Bart, J. C. J., Bassi, I. W. & Calcaterra, M. (1980). Acta Cryst. B36, 421-424.]); Karapetyan et al. (2008[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.]); Kabalka et al. (2005[Kabalka, G. W., Wu, Z., Ju, Y. & Yao, M.-L. (2005). J. Org. Chem. 70, 10285-10291.]); Podsiadlo & Katrusiak (2006[Podsiadlo, M. & Katrusiak, A. (2006). Acta Cryst. B62, 1071-1077.]); Klaeboe et al. (1986[Klaeboe, P., Klewe, B., Martinsen, K., Nielsen, C. J., Powell, D. L. & Stubbles, D. J. (1986). J. Mol. Struct. 140, 1-18.]).

[Scheme 1]

Experimental

Crystal data
  • C6H10Cl4

  • Mr = 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[alpha] radiation

  • [mu] = 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[Rigaku (2010). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.746, Tmax = 1.000

  • 8405 measured reflections

  • 1658 independent reflections

  • 1553 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.075

  • S = 1.12

  • 1658 reflections

  • 91 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1B...Cl3 0.99 2.76 3.2097 (19) 108
C4-H4B...Cl4 0.99 2.80 3.2445 (19) 108
C5-H5B...Cl1 0.99 2.74 3.2069 (19) 109
C6-H6B...Cl2 0.99 2.72 3.1940 (18) 110
C2-H2...Cl3i 1.00 2.93 3.8599 (19) 155
C3-H3...Cl2ii 1.00 2.86 3.8092 (19) 160
C4-H4B...Cl3i 0.99 2.92 3.657 (2) 132
C5-H5A...Cl2iii 0.99 2.90 3.6951 (19) 138
C6-H6A...Cl1iv 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[Rigaku (2010). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005[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.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort] [details]
Bart, J. C. J., Bassi, I. W. & Calcaterra, M. (1980). Acta Cryst. B36, 421-424.  [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Frenzen, G. & Coelhan, M. (1998). Private communication (refcode HITZOZ). CCDC, Cambridge, England.
Frenzen, G., Sippel, H. & Coelhan, M. (1999). Acta Cryst. C55, IUC9800079.  [CrossRef] [details]
Kabalka, G. W., Wu, Z., Ju, Y. & Yao, M.-L. (2005). J. Org. Chem. 70, 10285-10291.  [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [ChemPort]
Klaeboe, P., Klewe, B., Martinsen, K., Nielsen, C. J., Powell, D. L. & Stubbles, D. J. (1986). J. Mol. Struct. 140, 1-18.  [CrossRef] [ChemPort]
Podsiadlo, M. & Katrusiak, A. (2006). Acta Cryst. B62, 1071-1077.  [ISI] [CSD] [CrossRef] [details]
Rigaku (2010). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Weinges, K. & Spänig, R. (1968). Chem. Ber. 101, 3010-3017.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3495  [ doi:10.1107/S1600536812048398 ]

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