electronic reprintActa Crystallographica Section E

Structure ReportsOnline

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Diethyl 2,6-dihydroxy-4-(3-nitrophenyl)-2,6-bis(trifluoro-methyl)piperidine-3,5-dicarboxylate

Hoong-Kun Fun, Suhana Arshad, B. Palakshi Reddy, V. Vijayakumar and S.Sarveswari

Acta Cryst. (2012). E68, o400–o401

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Acta Cryst. (2012). E68, o400–o401 Fun et al. · C19H20F6N2O8

Diethyl 2,6-dihydroxy-4-(3-nitrophenyl)-2,6-bis(trifluoromethyl)piperidine-3,5-dicarboxylate

Hoong-Kun Fun,a*‡ Suhana Arshad,a B. Palakshi Reddy,b

V. Vijayakumarb and S. Sarveswarib

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800

USM, Penang, Malaysia, and bOrganic Chemistry Division, School of Advanced

Sciences, VIT University, Vellore 632 014, India

Correspondence e-mail: hkfun@usm.my

Received 16 December 2011; accepted 23 December 2011

Key indicators: single-crystal X-ray study; T = 296 K; mean �(C–C) = 0.003 A;

disorder in main residue; R factor = 0.044; wR factor = 0.125; data-to-parameter

ratio = 14.2.

In the title compound, C19H20F6N2O8, the ethoxy and ethyl

groups are disordered over two sets of sites, with occupancy

ratios of 0.212 (18):0.788 (18) and 0.746 (6):0.254 (6), respec-

tively. The piperidine ring adopts a chair conformation. In the

molecule, intramolecular O—H� � �O hydrogen bonds form

two S(6) ring motifs. In the crystal, molecules are linked via

O—H� � �O and C—H� � �O hydrogen bonds, forming dimers.

Related literature

For studies on 1,4-dihydropyridine and piperidones reported

by our group, see: Palakshi Reddy et al. (2011a,b,c); Rathore et

al. (2009); Rajesh et al. (2011). For bond-length data, see:

Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et

al. (1995). For ring conformations, see: Cremer & Pople

(1975).

Experimental

Crystal data

C19H20F6N2O8

Mr = 518.37Monoclinic, C2=ca = 17.7353 (16) Ab = 15.2025 (14) Ac = 17.3003 (16) A� = 91.049 (2)�

V = 4663.7 (7) A3

Z = 8Mo K� radiation� = 0.14 mm�1

T = 296 K0.21 � 0.21 � 0.14 mm

Data collection

Bruker SMART APEXII DUOCCD area-detectordiffractometer

Absorption correction: multi-scan(SADABS; Bruker, 2009)Tmin = 0.970, Tmax = 0.980

19801 measured reflections5339 independent reflections3229 reflections with I > 2�(I)Rint = 0.028

Refinement

R[F 2 > 2�(F 2)] = 0.044wR(F 2) = 0.125S = 1.025339 reflections376 parameters104 restraints

H atoms treated by a mixture ofindependent and constrainedrefinement

��max = 0.21 e A�3

��min = �0.19 e A�3

Table 1Hydrogen-bond geometry (A, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

O7—H1O7� � �O6 0.95 (3) 2.06 (3) 2.848 (2) 139 (3)O8—H1O8� � �O4 0.94 (3) 2.09 (3) 2.839 (2) 136 (2)O7—H1O7� � �O4i 0.95 (3) 2.28 (3) 2.882 (2) 121 (2)O8—H1O8� � �O6i 0.94 (3) 2.26 (3) 2.877 (2) 123 (2)C11—H11A� � �O7i 0.93 2.50 3.272 (2) 141C11—H11A� � �O8i 0.93 2.44 3.222 (2) 142

Symmetry code: (i) �x þ 12;�y þ 1

2;�z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT

(Bruker, 2009); data reduction: SAINT; program(s) used to solve

structure: SHELXTL (Sheldrick, 2008); program(s) used to refine

structure: SHELXTL; molecular graphics: SHELXTL; software used

to prepare material for publication: SHELXTL and PLATON (Spek,

2009).

The authors thank Universiti Sains Malaysia (USM) for the

Research University Grant (1001/PFIZIK/811160). SA thanks

the Malaysian Government and USM for the Academic Staff

Training Scheme (ASTS) award. BPR, VVand SS are grateful

to VIT University for providing facilities to carry out the

research work.

Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: RZ2690).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555–1573.

Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison,Wisconsin, USA.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

organic compounds

o400 Fun et al. doi:10.1107/S1600536811055346 Acta Cryst. (2012). E68, o400–o401

Acta Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

‡ Visiting Professor, College of Pharmacy, King Saud University, Riyadh,Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

electronic reprint

Palakshi Reddy, B., Rajesh, K. & Vijayakumar, V. (2011a). J. Chin. Chem. Soc.58, 384–388.

Palakshi Reddy, B., Rajesh, K. & Vijayakumar, V. (2011b). Arab. J. Chem.doi:10.1016/j.arabjc.2011.01.027.

Palakshi Reddy, B., Rajesh, K. & Vijayakumar, V. (2011c). Indian J.Heterocycl. Chem. 20, 281–282.

Rajesh, K., Palakshi Reddy, B. & Vijayakumar, V. (2011). Ultrason. Sonochem.doi:10.1016/j.ultsonch.2011.10.018.

Rathore, R. S., Reddy, B. P., Vijayakumar, V., Ragavan, R. V. &Narasimhamurthy, T. (2009). Acta Cryst. B65, 375–381.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.

organic compounds

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