rac-6-Hy­droxy-2,5,7,8-tetra­methyl­chroman-2-carboxamide from synchrotron data

Brzezinski, K.; Dauter, Z.; Baj, A.; Wałejko, P.; Witkowski, S.

doi:10.1107/S1600536811002807

Volume 67
Part 2
Pages o503-o504
February 2011

Received 12 January 2011
Accepted 20 January 2011
Online 29 January 2011

Key indicators
Single-crystal Synchrotron study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.050
wR = 0.147
Data-to-parameter ratio = 19.4
Details

rac-6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide from synchrotron data

Krzysztof Brzezinski,^a ^* Zbigniew Dauter,^a Aneta Baj,^b Piotr Walejko ^b and Stanislaw Witkowski ^b

^aSynchrotron Radiation Research Section, MCL, National Cancer Institute, Argonne National Laboratory, Biosciences Division, Bldg 202, Argonne, IL 60439, USA, and ^bInstitute of Chemistry, University of Bialystok, Pilsudskiego 11/4, 15-443 Bialystok, Poland
Correspondence e-mail: kbrzezinski@anl.gov

The crystal structure of the title water-soluble analogue of vitamin E, trolox amide, C₁₄H₁₉NO₃, solved and refined against synchrotron diffraction data, contains two molecules in the asymmetric unit. In both molecules, the heterocyclic ring is in a half-chair conformation. The crystal packing features a herring-bone pattern generated by N-HO hydrogen bonds between the hydroxy and amide groups. O-HO hydrogen bonds also occur.

Related literature

For background to the chemistry of trolox, its substituted amides and their applications as antioxidants and anti-inflamatory agents, see: Ross et al. (1995); Scott et al. (1974); Cort et al. (1975); Cohen et al. (1981); Walther et al. (1991); Silver et al. (1992); Netscher & Gautschi (1992); Van Ginkel et al. (1992); Moulin et al. (1998); Vajragupta et al. (2000); Koufaki et al. (2010). For the use of trolox as an intermediate for the synthesis of natural tocols such as vitamin E and [alpha] -tocotrienol, see: Cohen et al. (1979); Hyatt & Skelton (1997); Sakito & Suzokamo (1982); Sugai et al. (1991).

Experimental

Crystal data

C₁₄H₁₉NO₃
M_r = 249.31
Monoclinic, P 2₁ /c
a = 9.11 (1) Å
b = 17.92 (2) Å
c = 15.95 (1) Å
= 100.43 (1)°
V = 2561 (4) Å³
Z = 8
Synchrotron radiation
= 0.59040 Å
= 0.06 mm^-1
T = 100 K
0.2 × 0.05 × 0.04 mm

Data collection

MAR315 CCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 2003) T_min = 0.988, T_max = 0.997
14016 measured reflections
6360 independent reflections
5153 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.147
S = 1.08
6360 reflections
327 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N13-H13AO16ⁱ	0.88	2.13	2.971 (2)	160
N13-H13BO32ⁱⁱ	0.88	2.49	2.896 (3)	109
O16-H16AO32ⁱⁱⁱ	0.84	1.91	2.631 (2)	143
N33-H33BO12	0.88	2.29	2.861 (3)	123
N33-H33AO36ⁱ	0.88	2.53	3.281 (3)	143
O36-H36AO12^iv	0.84	1.91	2.727 (2)	165
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: NECAT APS beamline software; cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2304 ).

Acknowledgements

Financial support from the Polish Ministry of Science and Higher Education (grant No. N N204 177639) is gratefully acknowledged. This work was in part supported by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research. X-ray data were collected at the NECAT 24ID-C beamline of the Advanced Photon Source, Argonne National Laboratory. Use of the APS was supported by the US Department of Energy under contract No. W-31-109-Eng-38.

References

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organic compounds