Bis[5-chloro-2-(prop-2-yn-1-yl­oxy)phen­yl]methane

Qamar Ali; Itrat Anis; M Raza Shah; Seik Weng Ng

doi:10.1107/S1600536811003205

. 2011 Jan 29;67(Pt 2):o530. doi: 10.1107/S1600536811003205

Bis[5-chloro-2-(prop-2-yn-1-yloxy)phenyl]methane

Qamar Ali ^a, Itrat Anis ^a, M Raza Shah ^a, Seik Weng Ng ^b,^*

PMCID: PMC3051580 PMID: 21523178

Abstract

The molecule of the title compound, C₁₉H₁₄Cl₂O₂, has two benzene rings connected to a methylene C atom, and the rings are aligned at 66.3 (1)°. Intermolecular C—H⋯π and π–π stacking interactions are observed in the crystal structure, the centroid–centroid distances between parallel benzene rings being 3.7529 (12) and 3.6201 (12) Å, respectively.

Related literature

For a related structure, see: Hussain et al. (2009 ▶).

Experimental

Crystal data

C₁₉H₁₄Cl₂O₂
M _r = 345.20
Triclinic,
a = 8.4844 (5) Å
b = 9.7845 (6) Å
c = 11.2568 (6) Å
α = 86.258 (5)°
β = 71.412 (5)°
γ = 64.707 (6)°
V = 798.08 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.815, T _max = 1.000
6118 measured reflections
3523 independent reflections
2975 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.099
S = 1.00
3523 reflections
216 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003205/xu5147sup1.cif

e-67-0o530-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003205/xu5147Isup2.hkl

e-67-0o530-Isup2.hkl^{(172.7KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C11–C16 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cgⁱ	0.95	2.60	3.471 (2)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have reported several compounds that adopt a V-shape; this shape is induced by a methylene linkage to two aromatic systems. An example is bis[2-(3-bromopropoxy)-5-methylphenyl]methane, which methyl carbon has a widened angle of 115.0 (2)° (Hussain et al., 2009). The methylene angle in the present compound (Scheme I, Fig. 1) is similar [114.4 (1) °]. Two two aromatic rings that are connected the methylene carbon are aligned at 66.3 (1)°. Intermolecular C—H···π interaction occurs between inversion center related molecules (Table 1). π-π stacking is also present between parallel benzene rings in the crystal structure, centroid-to-centroid distances being 3.7529 (12) Å between C1-ring and C1ⁱ-ring (symmetry code: (i) 1-x, 1-y, 1-z), and 3.6201 (12) Å between C11-ring and C11ⁱⁱ-ring (symmetry code: (ii) 2-x, 1-y, -z).

Experimental

2, 2'-Methylenebis(4-chlorophenol) (1 g, 3.7 mmol) was dissolved in ethanol (30 ml). Potassium carbonate (1.5 g, 11 mmol) was added and the mixture was heated for an hour. Propargyl bromide (2 ml, 22 mmol) was added and the heating continues for another 3 h. Water (50 ml) was added. The organic compound was extracted by ethyl acetate (50 ml). Slow evaporation of ethyl acetate solution afforded crystals in 80% yield.