The Ar–Cl···HO hydrogen bond of 6-chloro-9-hydroxy-[3.3]metacyclophane

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Crystal data for 1: C₁₈H₁₉OCl, Mr = 286.80 g mo1⁻¹, colorless block (grown from n-hexane), size 0.90 × 0.55 × 0.18 mm, monoclinic, space group P21/a (#14), a = 13.839(1), b = 9.0890(6), c = 23.122(2) Å, β = 93.165(3)°, V = 2903.8(4) ų, Z = 8, ρ_calcd = 1.312 g cm⁻³, μ(Mo-Kα) = 2.56 cm⁻¹, F (000) = 1216.00, T = – 150.0 ± 1°C using the ω-2θ scan technique to a maximum 2θ value of 0.0°. A total of 25690 reflections were collected. The final cycle of the full-matrix least-squares refinement was based on 4173 observed reflections (I > 2.00σ (I)) and 373 variable parameters and converged with unweighted and weighted agreement factors of R = 0.079, Rw = 0.254, and GOF = 0.95. The maximum and minimum peaks on the final difference Fourier map corresponded to 0.50 and – 1.09 e^-/ų, respectively. Crystallographic data (excluding structure factor) for structure of 1 reported in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-230865. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-33603; e-mail: deposit@ccdc.cam.ac.uk).

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