Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Pages o110-o111
doi:10.1107/S1600536813034466

Di­methyl 5-acetyl-1-hy­dr­oxy-4-methyl-1H-pyrrole-2,3-di­carboxyl­ate, an oxidation-resistant N-hy­dr­oxy­pyrrole

Gerald M. Rosen,a Sukumaran Muralidharan,b Peter Y. Zavalijc and Joseph P. Y. Kaob,d*

aDepartment of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, Maryland 21201, USA, bCenter for Biomedical Engineering and Technology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA, cDepartment of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA, and dDepartment of Physiology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA
*Correspondence e-mail: jkao@umaryland.edu

(Received 3 December 2013; accepted 22 December 2013; online 4 January 2014)

The title compound, C11H13NO6, exhibits an intra­molecular O–H⋯O=C hydrogen bond between the N-hydroxyl H atom and carbonyl O atom of the neighboring acetyl group. This finding contradicts a previously published model in which the hydrogen bond was postulated to occur with the neighboring carbomethoxy group. This relatively strong hydrogen bond [O—H⋯O: D = 2.5583 (11) Å and θ = 152°] may underlie the resistance of the title compound to oxidation into the corresponding nitroxide.

CCDC reference: 978380

Related literature

The title compound was obtained as part of an effort to synthesize aromatic nitroxides and was prepared by a published procedure (Hekmatshoar et al., 2008[Hekmatshoar, R., Nouri, R. & Beheshtiha, S. Y. Sh. (2008). Heteroat. Chem. 19, 100-103.]). The compound could not be converted to the corresponding nitroxide under commonly used oxidation conditions (Keana et al., 1988[Keana, J. F. W., Heo, G. S., Mann, J. S., Van Nice, F. L., Lex, L., Prabhu, V. S. & Ferguson, G. (1988). J. Org. Chem. 53, 2268-2274.]). For analysis of intra­molecular hydrogen-bond parameters in organic crystals, see: Bilton et al. (2000[Bilton, C., Allen, F. H., Shields, G. P. & Howard, J. A. K. (2000). Acta Cryst. B56, 849-856.]); Galek et al. (2010[Galek, P. T. A., Fábián, L. & Allen, F. H. (2010). Acta Cryst. B66, 237-252.]). A survey of the effect of intra­molecular hydrogen bonding on the reduction potential of quinones appears in the review by Guin et al. (2011[Guin, P. S., Das, S. & Mandal, P. C. (2011). Int. J. Electrochem. vol. 2011, Article ID 816202, 22 pages, doi:10.4061/2011/816202.]). Examples of hydrogen bonding affecting the redox properties of quinones are discussed by Gupta & Linschitz (1997[Gupta, N. & Linschitz, H. (1997). J. Am. Chem. Soc. 119, 6384-6391.]) and Feldman et al. (2007[Feldman, K. S., Hester, D. K. II & Golbeck, J. H. (2007). Bioorg. Med. Chem. Lett. 17, 4891-4894.]).

[Scheme 1]

Experimental

Crystal data

  • C11H13NO6

  • Mr = 255.22

  • Monoclinic, P 21 /c

  • a = 10.3893 (8) Å

  • b = 15.1803 (12) Å

  • c = 7.5789 (6) Å

  • β = 99.630 (1)°

  • V = 1178.45 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 150 K

  • 0.52 × 0.43 × 0.31 mm
Data collection

  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.888, Tmax = 0.964

  • 19259 measured reflections

  • 3437 independent reflections

  • 2836 reflections with I > 2σ(I)

  • Rint = 0.014
Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.064

  • S = 1.00

  • 3437 reflections

  • 215 parameters

  • All H-atom parameters refined

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O5 0.888 (16) 1.746 (16) 2.5583 (11) 150.8 (14)

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XSHELL (Bruker, 2010[Bruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 978380

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813034466/ld2115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813034466/ld2115Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813034466/ld2115Isup3.cml

checkCIF report


Comment top

The title compound was synthesized by a published procedure (Hekmatshoar et al., 2008) with the goal of preparing the corresponding nitroxide by oxidation. The molecular structure is shown in Fig. 1. The compound proved resistant to several oxidizing conditions commonly used to convert N-hydroxylamines to nitroxides. Resistance of the title compound to oxidation may be attributable to the relatively strong hydrogen bond formed between the N-hydroxyl hydrogen and the carbonyl oxygen of the acetyl group in the 5-position. Modulation of redox properties by hydrogen bonding has been documented for quinones (see Guin et al. (2011) for review, Gupta and Linschitz (1997) and Feldman et al. (2007) for studies on specific series of benzoquinones and naphthoquinones, respectively). Existence of the intramolecular H-bond in the title compound is unsurprising, since in organic crystals where intramolecular hydrogen bonding would result in a planar 6-membered ring structure, the H-bond is almost always observed (Bilton et al., 2000). The observed O–H···O donor-acceptor distance (2.558 Å) is significantly shorter than the mean of 2.692 Å found for 8493 organic crystal structures in the Cambridge Structural Database in which the H-bond closes a 6-membered ring (Galek et al., 2010). Likewise, the observed O–H···O bond angle (150.8°) is significantly greater than the mean of 137.8° found for the same set of 8493 structures (Galek et al., 2010). These comparisons suggest that the intramolecular H-bond in the title compound is stronger than average. Finally, it may be interesting to note that, in the original paper reporting the synthesis of the title compound (Hekmatshoar et al., 2008), the authors suggested H-bonding between the N-hydroxyl hydrogen and the carbonyl oxygen of the ester group in the 2-position of the pyrrole ring.

Related literature top

The title compound was part of an effort to synthesize aromatic nitroxides and was prepared by a published procedure (Hekmatshoar et al., 2008). The compound could could not be converted to the corresponding nitroxide under commonly used oxidation conditions (Keana et al., 1988). For analysis of intramolecular hydrogen-bond parameters in organic crystals, see: Bilton et al. (2000); Galek et al. (2010). A survey of the effect of intramolecular hydrogen bonding on the reduction potential of quinones appears in the review by Guin et al. (2011); examples of hydrogen bonding affecting the redox properties of quinones are offered in the reports by Gupta & Linschitz (1997) and Feldman et al. (2007).

Experimental top

The title compound was prepared by the procedure of Hekmatshoar et al. (2008) in an effort to synthesize the corresponding nitroxide. The compound was subjected to four oxidation reactions: 1) m-chloroperbenzoic acid in CH2Cl2, 2) hydrogen peroxide–sodium tungstate in methanol/acetonitrile, 3) nickel peroxide in benzene, and 4) lead dioxide in benzene (Keana et al., 1988). In each case, no nitroxide was isolated, and only the title compound was recovered.

Refinement top

Positions of all H atoms were calculated from geometric considerations. H atoms were refined as riding on the attached C atoms. Orientation of CH3 groups was optimized. For all H atoms, Uiso was refined but constrained to be equal within CH3 groups.

Structure description top

The title compound was synthesized by a published procedure (Hekmatshoar et al., 2008) with the goal of preparing the corresponding nitroxide by oxidation. The molecular structure is shown in Fig. 1. The compound proved resistant to several oxidizing conditions commonly used to convert N-hydroxylamines to nitroxides. Resistance of the title compound to oxidation may be attributable to the relatively strong hydrogen bond formed between the N-hydroxyl hydrogen and the carbonyl oxygen of the acetyl group in the 5-position. Modulation of redox properties by hydrogen bonding has been documented for quinones (see Guin et al. (2011) for review, Gupta and Linschitz (1997) and Feldman et al. (2007) for studies on specific series of benzoquinones and naphthoquinones, respectively). Existence of the intramolecular H-bond in the title compound is unsurprising, since in organic crystals where intramolecular hydrogen bonding would result in a planar 6-membered ring structure, the H-bond is almost always observed (Bilton et al., 2000). The observed O–H···O donor-acceptor distance (2.558 Å) is significantly shorter than the mean of 2.692 Å found for 8493 organic crystal structures in the Cambridge Structural Database in which the H-bond closes a 6-membered ring (Galek et al., 2010). Likewise, the observed O–H···O bond angle (150.8°) is significantly greater than the mean of 137.8° found for the same set of 8493 structures (Galek et al., 2010). These comparisons suggest that the intramolecular H-bond in the title compound is stronger than average. Finally, it may be interesting to note that, in the original paper reporting the synthesis of the title compound (Hekmatshoar et al., 2008), the authors suggested H-bonding between the N-hydroxyl hydrogen and the carbonyl oxygen of the ester group in the 2-position of the pyrrole ring.

The title compound was part of an effort to synthesize aromatic nitroxides and was prepared by a published procedure (Hekmatshoar et al., 2008). The compound could could not be converted to the corresponding nitroxide under commonly used oxidation conditions (Keana et al., 1988). For analysis of intramolecular hydrogen-bond parameters in organic crystals, see: Bilton et al. (2000); Galek et al. (2010). A survey of the effect of intramolecular hydrogen bonding on the reduction potential of quinones appears in the review by Guin et al. (2011); examples of hydrogen bonding affecting the redox properties of quinones are offered in the reports by Gupta & Linschitz (1997) and Feldman et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: XSHELL (Bruker, 2010) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with non-hydrogen atoms labeled. Displacement ellipsoids are shown at the 60% probability level.
Dimethyl 5-acetyl-1-hydroxy-4-methyl-1H-pyrrole-2,3-dicarboxylate top
Crystal data top
C11H13NO6F(000) = 536
Mr = 255.22Dx = 1.439 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13127 reflections
a = 10.3893 (8) Åθ = 2.4–31.0°
b = 15.1803 (12) ŵ = 0.12 mm−1
c = 7.5789 (6) ÅT = 150 K
β = 99.630 (1)°Prism, colourless
V = 1178.45 (16) Å30.52 × 0.43 × 0.31 mm
Z = 4
Data collection top
Bruker SMART APEXII
diffractometer		3437 independent reflections
Radiation source: fine-focus sealed tube2836 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
Detector resolution: 8.333 pixels mm-1θmax = 30.0°, θmin = 2.0°
φ and ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −21→21
Tmin = 0.888, Tmax = 0.964l = −10→10
19259 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: difference Fourier map
wR(F2) = 0.064All H-atom parameters refined
S = 1.00 w = 1/[σ2(Fo2) + (0.01P)2 + 0.4962P], P = (max(Fo2,0) + 2Fc2)/3
3437 reflections(Δ/σ)max < 0.001
215 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C11H13NO6V = 1178.45 (16) Å3
Mr = 255.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3893 (8) ŵ = 0.12 mm−1
b = 15.1803 (12) ÅT = 150 K
c = 7.5789 (6) Å0.52 × 0.43 × 0.31 mm
β = 99.630 (1)°
Data collection top
Bruker SMART APEXII
diffractometer		3437 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2836 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.964Rint = 0.014
19259 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.064All H-atom parameters refined
S = 1.00Δρmax = 0.35 e Å−3
3437 reflectionsΔρmin = −0.19 e Å−3
215 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. For all H atoms both coordinate and isotropic displacement parameters were freely refined.

All H atoms were located from the difference Fourier maps and refined unconstrained including isotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.58967 (7)0.15991 (5)0.01532 (11)0.02245 (15)
C10.57608 (9)0.25121 (6)0.00825 (12)0.02170 (17)
C20.69238 (9)0.28546 (6)0.10473 (12)0.02101 (16)
C30.77256 (8)0.21282 (6)0.16540 (12)0.02102 (16)
C40.70478 (8)0.13542 (6)0.10655 (12)0.02093 (17)
O10.49892 (7)0.09969 (5)−0.06513 (11)0.03059 (16)
H10.4367 (15)0.1346 (10)−0.121 (2)0.055 (4)*
C50.45803 (9)0.28874 (6)−0.09308 (13)0.02522 (18)
O50.37225 (7)0.23953 (5)−0.17286 (11)0.03488 (18)
C60.44010 (11)0.38675 (7)−0.10178 (16)0.0318 (2)
H610.3632 (15)0.3989 (10)−0.190 (2)0.056 (4)*
H620.4261 (14)0.4098 (10)0.012 (2)0.048 (4)*
H630.5176 (13)0.4162 (9)−0.1332 (17)0.039 (4)*
C70.72552 (11)0.38090 (6)0.13774 (14)0.02725 (19)
H710.8031 (14)0.3861 (10)0.227 (2)0.050 (4)*
H720.6559 (14)0.4127 (9)0.1794 (18)0.044 (4)*
H730.7376 (13)0.4103 (9)0.0300 (19)0.044 (4)*
C80.90325 (9)0.21540 (6)0.27407 (13)0.02425 (18)
O80.96516 (8)0.28077 (5)0.32002 (13)0.0425 (2)
O90.94825 (7)0.13382 (5)0.31885 (10)0.02999 (16)
C91.07658 (11)0.13084 (9)0.42886 (18)0.0394 (3)
H911.0973 (16)0.0679 (11)0.439 (2)0.062 (5)*
H921.1394 (14)0.1618 (10)0.3656 (19)0.046 (4)*
H931.0726 (13)0.1588 (10)0.543 (2)0.046 (4)*
C100.74086 (8)0.04013 (6)0.13628 (12)0.02129 (17)
O100.70851 (7)−0.00387 (4)0.25304 (10)0.02722 (15)
O110.81287 (7)0.01306 (5)0.01819 (10)0.02943 (16)
C110.86684 (14)−0.07523 (8)0.04835 (18)0.0383 (3)
H1110.9238 (14)−0.0816 (9)−0.0377 (19)0.046 (4)*
H1120.9172 (15)−0.0775 (11)0.170 (2)0.060 (5)*
H1130.7977 (15)−0.1177 (11)0.037 (2)0.059 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0195 (3)0.0176 (3)0.0295 (4)−0.0019 (3)0.0019 (3)−0.0014 (3)
C10.0216 (4)0.0181 (4)0.0260 (4)0.0008 (3)0.0056 (3)0.0002 (3)
C20.0233 (4)0.0185 (4)0.0220 (4)−0.0006 (3)0.0061 (3)−0.0007 (3)
C30.0203 (4)0.0196 (4)0.0232 (4)−0.0016 (3)0.0038 (3)−0.0009 (3)
C40.0192 (4)0.0186 (4)0.0250 (4)−0.0002 (3)0.0040 (3)−0.0004 (3)
O10.0225 (3)0.0219 (3)0.0438 (4)−0.0053 (3)−0.0046 (3)−0.0031 (3)
C50.0224 (4)0.0257 (4)0.0284 (4)0.0036 (3)0.0068 (3)0.0028 (4)
O50.0246 (3)0.0322 (4)0.0446 (4)0.0018 (3)−0.0036 (3)0.0005 (3)
C60.0282 (5)0.0256 (5)0.0414 (6)0.0066 (4)0.0055 (4)0.0056 (4)
C70.0338 (5)0.0184 (4)0.0291 (5)−0.0026 (4)0.0039 (4)−0.0019 (4)
C80.0223 (4)0.0251 (4)0.0253 (4)−0.0020 (3)0.0037 (3)0.0002 (3)
O80.0323 (4)0.0298 (4)0.0591 (5)−0.0082 (3)−0.0103 (4)−0.0025 (4)
O90.0226 (3)0.0286 (4)0.0362 (4)0.0011 (3)−0.0027 (3)0.0030 (3)
C90.0268 (5)0.0473 (7)0.0399 (6)0.0063 (5)−0.0063 (4)0.0017 (5)
C100.0193 (4)0.0186 (4)0.0247 (4)−0.0003 (3)0.0001 (3)−0.0014 (3)
O100.0305 (3)0.0218 (3)0.0303 (3)−0.0020 (3)0.0079 (3)0.0013 (3)
O110.0368 (4)0.0229 (3)0.0308 (4)0.0106 (3)0.0120 (3)0.0057 (3)
C110.0488 (7)0.0259 (5)0.0442 (6)0.0169 (5)0.0190 (6)0.0075 (5)
Geometric parameters (Å, º) top
N1—C41.3304 (11)C7—H710.963 (15)
N1—O11.3799 (10)C7—H720.965 (14)
N1—C11.3932 (11)C7—H730.957 (14)
C1—C21.4033 (12)C8—O81.2020 (12)
C1—C51.4503 (13)C8—O91.3470 (12)
C2—C31.4118 (12)O9—C91.4501 (13)
C2—C71.5005 (13)C9—H910.980 (17)
C3—C41.4037 (12)C9—H920.991 (15)
C3—C81.4661 (12)C9—H930.971 (15)
C4—C101.5018 (12)C10—O101.2007 (11)
O1—H10.888 (16)C10—O111.3242 (11)
C5—O51.2399 (12)O11—C111.4561 (12)
C5—C61.4995 (14)C11—H1110.956 (14)
C6—H610.968 (15)C11—H1120.981 (16)
C6—H620.963 (15)C11—H1130.958 (16)
C6—H630.985 (14)
C4—N1—O1122.20 (8)C2—C7—H72112.0 (8)
C4—N1—C1111.99 (7)H71—C7—H72108.4 (11)
O1—N1—C1125.78 (8)C2—C7—H73111.6 (8)
N1—C1—C2106.00 (8)H71—C7—H73110.1 (12)
N1—C1—C5118.84 (8)H72—C7—H73104.9 (11)
C2—C1—C5135.11 (8)O8—C8—O9122.66 (9)
C1—C2—C3106.86 (8)O8—C8—C3125.82 (9)
C1—C2—C7126.74 (8)O9—C8—C3111.52 (8)
C3—C2—C7126.40 (8)C8—O9—C9114.87 (8)
C4—C3—C2108.24 (8)O9—C9—H91104.2 (10)
C4—C3—C8124.69 (8)O9—C9—H92108.9 (8)
C2—C3—C8127.06 (8)H91—C9—H92110.4 (12)
N1—C4—C3106.90 (8)O9—C9—H93109.0 (8)
N1—C4—C10121.82 (8)H91—C9—H93113.3 (13)
C3—C4—C10131.24 (8)H92—C9—H93110.7 (12)
N1—O1—H1101.8 (10)O10—C10—O11125.81 (8)
O5—C5—C1119.78 (9)O10—C10—C4123.55 (8)
O5—C5—C6120.16 (9)O11—C10—C4110.64 (8)
C1—C5—C6120.06 (9)C10—O11—C11115.20 (8)
C5—C6—H61107.5 (9)O11—C11—H111104.6 (9)
C5—C6—H62111.0 (9)O11—C11—H112108.1 (10)
H61—C6—H62108.4 (12)H111—C11—H112110.1 (12)
C5—C6—H63111.2 (8)O11—C11—H113110.0 (9)
H61—C6—H63111.1 (11)H111—C11—H113114.3 (13)
H62—C6—H63107.6 (11)H112—C11—H113109.5 (13)
C2—C7—H71109.7 (9)
C4—N1—C1—C2−0.55 (11)C2—C3—C4—C10−177.93 (9)
O1—N1—C1—C2−178.69 (8)C8—C3—C4—C101.01 (15)
C4—N1—C1—C5177.39 (8)N1—C1—C5—O5−0.77 (14)
O1—N1—C1—C5−0.75 (14)C2—C1—C5—O5176.43 (10)
N1—C1—C2—C30.48 (10)N1—C1—C5—C6179.45 (9)
C5—C1—C2—C3−176.97 (10)C2—C1—C5—C6−3.36 (16)
N1—C1—C2—C7−179.43 (9)C4—C3—C8—O8176.89 (10)
C5—C1—C2—C73.13 (17)C2—C3—C8—O8−4.37 (16)
C1—C2—C3—C4−0.26 (10)C4—C3—C8—O9−3.19 (13)
C7—C2—C3—C4179.64 (9)C2—C3—C8—O9175.56 (9)
C1—C2—C3—C8−179.17 (9)O8—C8—O9—C90.77 (15)
C7—C2—C3—C80.73 (15)C3—C8—O9—C9−179.15 (9)
O1—N1—C4—C3178.61 (8)N1—C4—C10—O10−82.60 (12)
C1—N1—C4—C30.39 (11)C3—C4—C10—O1094.99 (12)
O1—N1—C4—C10−3.29 (14)N1—C4—C10—O1197.95 (10)
C1—N1—C4—C10178.50 (8)C3—C4—C10—O11−84.45 (12)
C2—C3—C4—N1−0.07 (10)O10—C10—O11—C11−6.69 (15)
C8—C3—C4—N1178.87 (8)C4—C10—O11—C11172.74 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O50.888 (16)1.746 (16)2.5583 (11)150.8 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O50.888 (16)1.746 (16)2.5583 (11)150.8 (14)
 

Acknowledgements

This work was supported in part by grants GM056481 (JPYK) and ER2034 (GMR) from the US National Institutes of Health.

References

First citationBilton, C., Allen, F. H., Shields, G. P. & Howard, J. A. K. (2000). Acta Cryst. B56, 849–856.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationBruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFeldman, K. S., Hester, D. K. II & Golbeck, J. H. (2007). Bioorg. Med. Chem. Lett. 17, 4891–4894.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationGalek, P. T. A., Fábián, L. & Allen, F. H. (2010). Acta Cryst. B66, 237–252.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationGuin, P. S., Das, S. & Mandal, P. C. (2011). Int. J. Electrochem. vol. 2011, Article ID 816202, 22 pages, doi:10.4061/2011/816202.  Google Scholar
 First citationGupta, N. & Linschitz, H. (1997). J. Am. Chem. Soc. 119, 6384–6391.  CrossRef CAS Web of Science Google Scholar
 First citationHekmatshoar, R., Nouri, R. & Beheshtiha, S. Y. Sh. (2008). Heteroat. Chem. 19, 100–103.  Web of Science CrossRef CAS Google Scholar
 First citationKeana, J. F. W., Heo, G. S., Mann, J. S., Van Nice, F. L., Lex, L., Prabhu, V. S. & Ferguson, G. (1988). J. Org. Chem. 53, 2268–2274.  CSD CrossRef CAS Web of Science Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Pages o110-o111
doi:10.1107/S1600536813034466
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS