PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o473.
Published online 2009 February 6. doi:  10.1107/S1600536809000609
PMCID: PMC2968677

1,4-Bis[3-chloro-2-(chloro­meth­yl)prop­yl]benzene

Abstract

The title mol­ecule, C14H18Cl4, possesses a crystallographically imposed inversion centre, which coincides with the centre of benzene ring. In the absence of classical inter­molecular inter­actions, van der Waals forces help the mol­ecules to pack in the crystal.

Related literature

For related crystal structures, see: Chen et al. (2005 [triangle]); Gao et al. (2009 [triangle]). For general background, see Amabilino & Stoddart (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o473-scheme1.jpg

Experimental

Crystal data

  • C14H18Cl4
  • M r = 328.08
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o473-efi1.jpg
  • a = 6.518 (3) Å
  • b = 14.680 (6) Å
  • c = 8.433 (4) Å
  • β = 106.335 (5)°
  • V = 774.3 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.75 mm−1
  • T = 291 (2) K
  • 0.30 × 0.26 × 0.24 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.807, T max = 0.842
  • 4423 measured reflections
  • 1679 independent reflections
  • 1275 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.113
  • S = 1.09
  • 1679 reflections
  • 82 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000609/cv2502sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000609/cv2502Isup2.hkl

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

Acknowledgments

The authors acknowledge the financial support of Jiangsu Polytechnic University, the Natural Science Foundation of China (grant No. 20872051) and the Key Laboratory of Fine Petrochemical Engineering of Jiangsu Province (grant No. KF0503).

supplementary crystallographic information

Comment

The molecular recognition between a π-electron-rich hydroquinone ring and π-electron-deficient cyclophane has provided the inspiration for the self-assembly of a large number of catenanes (Amabilino & Stoddart, 1995). In our study of the applications of fused bipyridine cyclophane compounds in the self-assembly of supramolecular systems, we obtained tetraethyl 2,2'-(p-phenylenedimethylene)dimalonate (Chen et al., 2005), which was used in the synthesis of 2,2'-(p-phenylenedimethylene)bis(propane-1,3-diol) (Gao et al., 2009). The title compound, (I), was obtained by the chlorination of the diol. Herewith we present the crystal structure of (I) (Fig. 1).

Experimental

The 2,2'-(p-phenylenedimethylene)bis(propane-1,3-diol), used in this study, was obtained in accordance with the Gao et al. (2005). In a flame-dryed, round-bottomed flask was placed SOCl2(5 mL) and p-C6H4[CH2CH(CH2OH)2]2(0.508 g,2 mmol) was slowly added under stirring. The mixture was heated up to 333 K. The solvent was evaporated and the resulting oil was chromatographed on a silica-gel column, yielding the title compound (0.51 g, 77%). M.p. 353–354 K.

Refinement

All H atoms were geometrically positioned (C–H 0.93-0.98%A) and treated as riding, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) showing the atom-labelling scheme and 30% probability displacement ellipsoids [symmetry code: (A)-x, -y + 2, -z + 1].

Crystal data

C14H18Cl4F(000) = 340
Mr = 328.08Dx = 1.407 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1607 reflections
a = 6.518 (3) Åθ = 2.8–26.1°
b = 14.680 (6) ŵ = 0.75 mm1
c = 8.433 (4) ÅT = 291 K
β = 106.335 (5)°Block, colourless
V = 774.3 (6) Å30.30 × 0.26 × 0.24 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer1679 independent reflections
Radiation source: sealed tube1275 reflections with I > 2σ(I)
graphiteRint = 0.066
[var phi] and ω scansθmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −8→7
Tmin = 0.807, Tmax = 0.842k = −18→14
4423 measured reflectionsl = −10→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0483P)2 + 0.0345P] where P = (Fo2 + 2Fc2)/3
1679 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = −0.32 e Å3

Special details

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.The structures were solved with direct methods and refined with full-matrix least-squares techniques using the SHELXTL. The coordinates of the non-hydrogen atoms were refined anisotropically, and the positions of the H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2 timesUeq(C).
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)

xyzUiso*/Ueq
C10.1873 (3)0.97482 (12)0.6208 (2)0.0415 (4)
C20.0205 (4)1.01687 (13)0.6634 (2)0.0482 (5)
H20.03271.02840.77410.058*
C3−0.1637 (3)1.04196 (13)0.5447 (3)0.0477 (5)
H3−0.27331.07050.57640.057*
C40.3901 (3)0.94730 (13)0.7505 (3)0.0489 (5)
H7A0.39990.98120.85110.059*
H7B0.51230.96380.71220.059*
C50.4008 (3)0.84467 (13)0.7898 (2)0.0410 (4)
H80.39840.81230.68770.049*
C60.6155 (3)0.82501 (15)0.9136 (3)0.0543 (5)
H9A0.61740.85151.01940.065*
H9B0.72750.85390.87640.065*
C70.2135 (3)0.81085 (13)0.8444 (2)0.0444 (5)
H10A0.22730.74560.86290.053*
H10B0.08280.82180.75710.053*
Cl10.67066 (10)0.70596 (4)0.94037 (8)0.0736 (3)
Cl20.19547 (9)0.86582 (4)1.03025 (7)0.0635 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0465 (11)0.0298 (9)0.0488 (11)−0.0015 (8)0.0141 (9)0.0050 (8)
C20.0586 (13)0.0437 (11)0.0440 (11)0.0046 (9)0.0172 (10)−0.0002 (8)
C30.0535 (12)0.0389 (11)0.0560 (12)0.0063 (9)0.0241 (10)0.0036 (9)
C40.0424 (11)0.0438 (11)0.0570 (12)−0.0062 (8)0.0082 (9)0.0026 (9)
C50.0389 (10)0.0396 (10)0.0443 (10)0.0017 (8)0.0114 (8)−0.0017 (8)
C60.0368 (11)0.0513 (12)0.0718 (14)0.0052 (9)0.0101 (10)0.0022 (10)
C70.0397 (11)0.0414 (11)0.0480 (11)−0.0012 (8)0.0058 (9)0.0009 (8)
Cl10.0629 (4)0.0603 (4)0.0915 (5)0.0227 (3)0.0119 (3)0.0086 (3)
Cl20.0614 (4)0.0795 (4)0.0538 (4)0.0101 (3)0.0228 (3)0.0004 (3)

Geometric parameters (Å, °)

C1—C3i1.382 (3)C5—C71.504 (3)
C1—C21.383 (3)C5—C61.520 (3)
C1—C41.515 (3)C5—H80.9800
C2—C31.380 (3)C6—Cl11.786 (2)
C2—H20.9300C6—H9A0.9700
C3—C1i1.382 (3)C6—H9B0.9700
C3—H30.9300C7—Cl21.796 (2)
C4—C51.540 (3)C7—H10A0.9700
C4—H7A0.9700C7—H10B0.9700
C4—H7B0.9700
C3i—C1—C2118.01 (19)C6—C5—C4108.10 (16)
C3i—C1—C4120.55 (19)C7—C5—H8107.2
C2—C1—C4121.44 (18)C6—C5—H8107.2
C3—C2—C1121.17 (19)C4—C5—H8107.2
C3—C2—H2119.4C5—C6—Cl1112.74 (15)
C1—C2—H2119.4C5—C6—H9A109.0
C2—C3—C1i120.82 (19)Cl1—C6—H9A109.0
C2—C3—H3119.6C5—C6—H9B109.0
C1i—C3—H3119.6Cl1—C6—H9B109.0
C1—C4—C5113.20 (15)H9A—C6—H9B107.8
C1—C4—H7A108.9C5—C7—Cl2112.11 (13)
C5—C4—H7A108.9C5—C7—H10A109.2
C1—C4—H7B108.9Cl2—C7—H10A109.2
C5—C4—H7B108.9C5—C7—H10B109.2
H7A—C4—H7B107.8Cl2—C7—H10B109.2
C7—C5—C6113.40 (16)H10A—C7—H10B107.9
C7—C5—C4113.42 (15)
C3i—C1—C2—C3−0.4 (3)C1—C4—C5—C6176.91 (17)
C4—C1—C2—C3179.85 (17)C7—C5—C6—Cl164.6 (2)
C1—C2—C3—C1i0.4 (3)C4—C5—C6—Cl1−168.74 (14)
C3i—C1—C4—C5−77.5 (2)C6—C5—C7—Cl262.71 (19)
C2—C1—C4—C5102.2 (2)C4—C5—C7—Cl2−61.10 (19)
C1—C4—C5—C7−56.4 (2)

Symmetry codes: (i) −x, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2502).

References

  • Amabilino, D. B. & Stoddart, J. F. (1995). Chem. Rev.95, 2725–2737.
  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc. Madison, Wisconsin, USA.
  • Chen, A.-H., Wang, Z.-G., Yin, G.-D. & Wu, A.-X. (2005). Acta Cryst. E61, o3240–o3241.
  • Gao, Y., Xi, H., Sun, X., Fu, Y. & Liu, L. (2009). Acta Cryst. E65, o170. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography