The title compound, C6H8O3, is the smallest keto acid yet found to aggregate in the solid as acid-to-ketone hydrogen-bonded catemers. Four translational chains pass through the cell in the a direction [O...O = 2.6915 (14) A and O-H...O = 166 degrees]. Two intermolecular C-H...O close contacts exist, involving both carbonyl functions.
Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.038; wR factor = 0.104; data-to-parameter ratio = 13.6. organic compounds o3606 # 2007 International Union of Crystallography
Key indicatorsSingle-crystal X-ray study T = 100 K Mean (C-C) = 0.002 Å R factor = 0.037 wR factor = 0.096 Data-to-parameter ratio = 12.7For details of how these key indicators were automatically derived from the article, see
Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.003 Å; R factor = 0.051; wR factor = 0.156; data-to-parameter ratio = 11.0.The title compound, C 9 H 8 O 3 , adopts a conformation in which both substituents lie nearly coplanar with the ring. Asymmetric units aggregate by centrosymmetric carboxyl pairing. Close offset stacking of rings in parallel planes creates intermolecular CÁ Á ÁCcontacts of 3.322 (3) and 3.352 (3) Å , with an accompanying CÁ Á ÁOcontact of 3.147 (3) Å and similarly close interactions between O atoms and aromatic systems. One close intermolecular C-HÁ Á ÁO contact is also present.
CommentOur study of solid-state H-bonding patterns in ketocarboxylic acids has employed several examples of fundamentally simple systems to explore the minimum requirements for various H-bonding modes. Among such compounds is the title aromatic.
Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.036; wR factor = 0.095; data-to-parameter ratio = 13.0. The title racemate (C 11 H 14 O 3 ) aggregates in the solid as acidto-ketone hydrogen-bonding catemers [OÁ Á ÁO = 2.6557 (13) Å and O-HÁ Á ÁO = 170 ], whose components are glide-related. The stereochemistry of the carboxyl group arises spontaneously during the synthesis. One intermolecular C-HÁ Á ÁO C close contact was found. Experimental Crystal data C 11 H 14 O 3 M r = 194.22 Monoclinic, P2 1 =c a = 5.2691 (3) Å b = 16.1279 (11) Å c = 11.9181 (7) Å = 98.252 (3) V = 1002.31 (11) Å 3 Z = 4 Cu K radiation = 0.76 mm À1 T = 100 (2) K 0.38 Â 0.36 Â 0.16 mm Data collection Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T min = 0.78, T max = 0.86 5164 measured reflections 1662 independent reflections 1600 reflections with I > 2(I) R int = 0.018
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