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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-Azido-2-de­­oxy-3,4-O-iso­propyl­­idene-2-C-methyl-D-talono-1,5-lactone

aDepartment of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, and bDepartment of Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England
*Correspondence e-mail: sarah.jenkinson@chem.ox.ac.uk

(Received 19 April 2010; accepted 23 April 2010; online 30 April 2010)

The relative stereochemistry of the title compound, C10H15N3O5, was confirmed by the crystal structure determin­ation. The absolute configuration was determined from the use of D-lyxonolactone as the starting material. The six-membered ring adopts a boat conformation with the larger azide group, rather than the methyl group, in the bowsprit position. In the crystal structure, a bifurcated inter­molecular O—H⋯O/O—H⋯N hydrogen bond links mol­ecules into chains running parallel to the b axis.

Related literature

For carbohydrates as chirons, see: Lichtenthaler & Peters (2004[Lichtenthaler, F. W. & Peters, S. (2004). C. R. Chim. 7, 65-90.]); Fechter et al. (1999[Fechter, M. H., Stutz, A. E. & Tauss, A. (1999). Curr. Org. Chem. 3, 269-285.]); Fleet (1989[Fleet, G. W. J. (1989). Chem. Br. 25, 287-291.]). For branched sugars and their use as chirons, see: Rao et al. (2008[Rao, D., Yoshihara, A., Gullapalli, P., Morimoto, K., Takata, G., da Cruz, F. P., Jenkinson, S. F., Wormald, M. R., Dwek, R. A., Fleet, G. W. J. & Izumori, K. (2008). Tetrahedron Lett. 49, 3316-3121.]); Jones et al. (2008[Jones, N. A., Rao, D., Yoshihara, A., Gullapalli, P., Morimoto, K., Takata, G., Hunter, S. J., Wormald, M. R., Dwek, R. A., Izumori, K. & Fleet, G. W. J. (2008). Tetrahedron Asymmetry, 19, 1904-1918.]); Booth et al. (2008[Booth, K. V., da Cruz, F. P., Hotchkiss, D. J., Jenkinson, S. F., Jones, N. A., Weymouth-Wilson, A. C., Clarkson, R., Heinz, T. & Fleet, G. W. J. (2008). Tetrahedron: Asymmetry, 19, 2417-2424.]); Hotchkiss, Kato et al. (2007[Hotchkiss, D. J., Kato, A., Odell, B., Claridge, T. D. W. & Fleet, G. W. J. (2007). Tetrahedron Asymmetry, 18, 500-512.]); da Cruz et al. (2008[Cruz, F. P. da, Horne, G. & Fleet, G. W. J. (2008). Tetrahedron Lett. 49, 6812-6815.]); Soengas et al. (2005[Soengas, R., Izumori, K., Simone, M. I., Watkin, D. J., Skytte, U. P., Soetaert, W. & Fleet, G. W. J. (2005). Tetrahedron Lett. 46, 5755-5759.]). For the structures of similar sugars, see: Chesterton et al. (2006[Chesterton, A. K. S., Jenkinson, S. F., Jones, N. A., Fleet, G. W. J. & Watkin, D. J. (2006). Acta Cryst. E62, o2983-o2985.]); Booth et al. (2007[Booth, K. V., Watkin, D. J., Jenkinson, S. F. & Fleet, G. W. J. (2007). Acta Cryst. E63, o1759-o1760.]); Hotchkiss, Jenkinson et al. (2007[Hotchkiss, D. J., Jenkinson, S. F., Booth, K. V., Fleet, G. W. J. & Watkin, D. J. (2007). Acta Cryst. E63, o2168-o2170.]); Baird et al. (1987[Baird, P. D., Dho, J. C., Fleet, G. W. J., Peach, J. M., Prout, K. & Smith, P. W. (1987). J. Chem. Soc. Perkin Trans. 1, pp. 1785-1791.]); Bruce et al. (1990[Bruce, I., Fleet, G. W. J., Girdhar, A., Haraldsson, M., Peach, J. M. & Watkin, D. J. (1990). Tetrahedron, 46, 19-32.]); Punzo et al. (2005[Punzo, F., Watkin, D. J., Jenkinson, S. F., Cruz, F. P. & Fleet, G. W. J. (2005). Acta Cryst. E61, o511-o512.]). For the extinction correction, see: Larson (1970[Larson, A. C. (1970). Crystallographic Computing, Edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291-294. Copenhagen: Munksgaard.]).

[Scheme 1]

Experimental

Crystal data
  • C10H15N3O5

  • Mr = 257.25

  • Orthorhombic, P 21 21 21

  • a = 5.9481 (3) Å

  • b = 13.3427 (7) Å

  • c = 15.6351 (9) Å

  • V = 1240.86 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 150 K

  • 0.20 × 0.15 × 0.05 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.89, Tmax = 0.99

  • 10775 measured reflections

  • 1647 independent reflections

  • 1170 reflections with I > 2σ(I)

  • Rint = 0.077

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.087

  • S = 0.88

  • 1647 reflections

  • 164 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O15—H151⋯O1i 0.84 2.14 2.930 (4) 157
O15—H151⋯N7i 0.84 2.52 3.072 (4) 125
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: CRYSTALS.

Supporting information


Comment top

Carbohydrates are a diverse set of chirons for the synthesis of complex amino acids and iminosugars (Lichtenthaler & Peters, 2004; Fechter et al., 1999; Fleet, 1989). 2-C-Methyl branched sugars constitute a class of rare sugars with chemotherapeutic potential (Rao et al., 2008; Jones et al., 2008; Booth et al., 2008) and can be used as building blocks in the synthesis of biologically active compounds (da Cruz et al., 2008; Hotchkiss, Kato et al., 2007; Soengas et al., 2005).

The azidolactone 3 (Fig. 1) would be a key intermediate for the synethsis of branched pyrrolidines, piperidines and prolines derived from D-lyxonolactone. Nucleophilic displacement of a triflate leaving group at the tertiary centre by azide was confirmed by X-ray crystallography to have proceeded with overall inversion of configuration (Booth et al. 2007; Hotchkiss, Jenkinson et al. 2007). The 6-membered lactone ring adopts a boat conformation, as is common with 3,4-O-isopropylidene-1,5-lactones (Baird et al., 1987; Bruce et al., 1990; Punzo et al., 2005), with the larger azide group, rather than the methyl, in the bowsprit position (Fig. 2). The absolute configuration was determined from the use of D-lyxonolactone as the starting material. As is common with these materials the azide is non linear [N7 - N8 - N9 = 172.4 (3) °] (Chesterton et al., 2006), with the anisotropic atomic displacement parameter of the central atom lowered with respect to its neighbours. The compound exists as hydrogen bonded chains of molecules running parallel to the b-axis (Fig. 3). The hydrogen bond is bifurcated. Only classical hydrogen bonding is considered.

Related literature top

For carbohydrates as chirons, see: Lichtenthaler & Peters (2004); Fechter et al. (1999); Fleet (1989). For branched sugars and their use as chirons, see: Rao et al. (2008); Jones et al. (2008); Booth et al. (2008); Hotchkiss, Kato et al. (2007); da Cruz et al. (2008); Soengas et al. (2005). For the structures of similar sugars, see: Chesterton et al. (2006); Booth et al. (2007); Hotchkiss, Jenkinson et al. (2007); Baird et al. (1987); Bruce et al. (1990); Punzo et al. (2005). For the extinction correction, see: Larson (1970).

Experimental top

The title compound was recrystallised by slow evaporation from a mixture of diethyl ether and cyclohexane: m.p. 397-403 K, [α]D25 +112.4 (c, 1.145 in CHCl3).

Refinement top

In the absence of significant anomalous scattering, Friedel pairs were merged and the absolute configuration was assigned from the use of D-lyonolactone as the starting material.

The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, O—H = 0.82 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.

Structure description top

Carbohydrates are a diverse set of chirons for the synthesis of complex amino acids and iminosugars (Lichtenthaler & Peters, 2004; Fechter et al., 1999; Fleet, 1989). 2-C-Methyl branched sugars constitute a class of rare sugars with chemotherapeutic potential (Rao et al., 2008; Jones et al., 2008; Booth et al., 2008) and can be used as building blocks in the synthesis of biologically active compounds (da Cruz et al., 2008; Hotchkiss, Kato et al., 2007; Soengas et al., 2005).

The azidolactone 3 (Fig. 1) would be a key intermediate for the synethsis of branched pyrrolidines, piperidines and prolines derived from D-lyxonolactone. Nucleophilic displacement of a triflate leaving group at the tertiary centre by azide was confirmed by X-ray crystallography to have proceeded with overall inversion of configuration (Booth et al. 2007; Hotchkiss, Jenkinson et al. 2007). The 6-membered lactone ring adopts a boat conformation, as is common with 3,4-O-isopropylidene-1,5-lactones (Baird et al., 1987; Bruce et al., 1990; Punzo et al., 2005), with the larger azide group, rather than the methyl, in the bowsprit position (Fig. 2). The absolute configuration was determined from the use of D-lyxonolactone as the starting material. As is common with these materials the azide is non linear [N7 - N8 - N9 = 172.4 (3) °] (Chesterton et al., 2006), with the anisotropic atomic displacement parameter of the central atom lowered with respect to its neighbours. The compound exists as hydrogen bonded chains of molecules running parallel to the b-axis (Fig. 3). The hydrogen bond is bifurcated. Only classical hydrogen bonding is considered.

For carbohydrates as chirons, see: Lichtenthaler & Peters (2004); Fechter et al. (1999); Fleet (1989). For branched sugars and their use as chirons, see: Rao et al. (2008); Jones et al. (2008); Booth et al. (2008); Hotchkiss, Kato et al. (2007); da Cruz et al. (2008); Soengas et al. (2005). For the structures of similar sugars, see: Chesterton et al. (2006); Booth et al. (2007); Hotchkiss, Jenkinson et al. (2007); Baird et al. (1987); Bruce et al. (1990); Punzo et al. (2005). For the extinction correction, see: Larson (1970).

Computing details top

Data collection: COLLECT (Nonius, 2001).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top
[Figure 1] Fig. 1. Synthetic Scheme
[Figure 2] Fig. 2. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
[Figure 3] Fig. 3. Packing diagram for the title compound projected along the a-axis. Hydrogen bonds are shown by dotted lines.
2-Azido-2-deoxy-3,4-O-isopropylidene-2-C-methyl-D-talono-1,5-lactone top
Crystal data top
C10H15N3O5F(000) = 544
Mr = 257.25Dx = 1.377 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1637 reflections
a = 5.9481 (3) Åθ = 5–27°
b = 13.3427 (7) ŵ = 0.11 mm1
c = 15.6351 (9) ÅT = 150 K
V = 1240.86 (12) Å3Plate, colourless
Z = 40.20 × 0.15 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
1170 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
ω scansθmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
h = 77
Tmin = 0.89, Tmax = 0.99k = 1717
10775 measured reflectionsl = 2020
1647 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038 Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.05P)2 + 0.16P],
where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.087(Δ/σ)max = 0.000278
S = 0.88Δρmax = 0.53 e Å3
1647 reflectionsΔρmin = 0.45 e Å3
164 parametersExtinction correction: Larson (1970), Equation 22
0 restraintsExtinction coefficient: 460 (60)
Primary atom site location: structure-invariant direct methods
Crystal data top
C10H15N3O5V = 1240.86 (12) Å3
Mr = 257.25Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.9481 (3) ŵ = 0.11 mm1
b = 13.3427 (7) ÅT = 150 K
c = 15.6351 (9) Å0.20 × 0.15 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
1647 independent reflections
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
1170 reflections with I > 2σ(I)
Tmin = 0.89, Tmax = 0.99Rint = 0.077
10775 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 0.88Δρmax = 0.53 e Å3
1647 reflectionsΔρmin = 0.45 e Å3
164 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4977 (3)0.87439 (12)0.79200 (10)0.0276
C20.5736 (5)0.85325 (19)0.87769 (16)0.0297
O30.7326 (3)0.77432 (13)0.86551 (10)0.0334
C40.8307 (4)0.78267 (17)0.78210 (15)0.0258
C50.6901 (4)0.86484 (17)0.73767 (14)0.0250
C60.6110 (4)0.83522 (18)0.64929 (15)0.0247
N70.4436 (4)0.91275 (16)0.62475 (14)0.0317
N80.3742 (4)0.90581 (16)0.55031 (15)0.0313
N90.2976 (4)0.90888 (18)0.48383 (15)0.0443
C100.4914 (4)0.73333 (18)0.65603 (15)0.0243
O110.3123 (3)0.71606 (13)0.62348 (11)0.0323
O120.5913 (3)0.66364 (12)0.70449 (11)0.0256
C130.8169 (4)0.68186 (17)0.73740 (16)0.0250
C140.8716 (5)0.59403 (17)0.79413 (17)0.0309
O150.8866 (3)0.50433 (11)0.74599 (11)0.0351
C160.8056 (4)0.83600 (19)0.58502 (16)0.0303
C170.6857 (5)0.9437 (2)0.91665 (18)0.0385
C180.3762 (5)0.8142 (2)0.92680 (19)0.0459
H410.99050.80320.78720.0311*
H510.77400.92840.73500.0310*
H1310.92350.68130.68880.0288*
H1411.01800.60750.82090.0398*
H1420.75520.58730.83880.0391*
H1610.74610.81670.52920.0461*
H1620.87070.90270.58180.0463*
H1630.92190.78930.60240.0460*
H1720.73910.92580.97300.0598*
H1710.57430.99720.92060.0603*
H1730.81130.96350.87970.0603*
H1820.42600.79570.98450.0690*
H1810.26040.86550.92970.0694*
H1830.31740.75590.89750.0688*
H1510.75910.47780.74530.0532*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0272 (9)0.0348 (9)0.0207 (8)0.0036 (8)0.0008 (8)0.0009 (7)
C20.0358 (14)0.0323 (13)0.0209 (12)0.0025 (12)0.0027 (11)0.0011 (12)
O30.0480 (11)0.0305 (9)0.0217 (9)0.0089 (9)0.0031 (8)0.0004 (8)
C40.0254 (13)0.0278 (12)0.0241 (13)0.0041 (11)0.0031 (10)0.0007 (11)
C50.0249 (12)0.0250 (12)0.0252 (12)0.0006 (10)0.0006 (11)0.0016 (11)
C60.0253 (12)0.0255 (12)0.0233 (13)0.0057 (11)0.0011 (11)0.0031 (10)
N70.0361 (12)0.0337 (11)0.0253 (11)0.0090 (10)0.0035 (10)0.0003 (10)
N80.0309 (12)0.0300 (11)0.0330 (13)0.0066 (10)0.0013 (11)0.0030 (11)
N90.0446 (14)0.0544 (16)0.0340 (14)0.0089 (13)0.0105 (12)0.0052 (12)
C100.0210 (12)0.0297 (13)0.0221 (11)0.0039 (11)0.0023 (11)0.0047 (11)
O110.0255 (9)0.0391 (10)0.0322 (10)0.0029 (9)0.0047 (8)0.0022 (9)
O120.0228 (8)0.0246 (8)0.0293 (9)0.0005 (7)0.0023 (7)0.0012 (8)
C130.0192 (11)0.0267 (12)0.0292 (14)0.0008 (10)0.0021 (11)0.0020 (11)
C140.0327 (14)0.0247 (12)0.0351 (14)0.0018 (12)0.0044 (12)0.0045 (12)
O150.0297 (9)0.0248 (9)0.0509 (12)0.0035 (8)0.0037 (9)0.0003 (9)
C160.0318 (13)0.0317 (13)0.0274 (13)0.0010 (12)0.0036 (11)0.0049 (11)
C170.0484 (17)0.0374 (15)0.0297 (14)0.0015 (14)0.0060 (14)0.0059 (12)
C180.0446 (17)0.063 (2)0.0300 (16)0.0052 (15)0.0033 (13)0.0041 (15)
Geometric parameters (Å, º) top
O1—C21.442 (3)C10—O121.338 (3)
O1—C51.431 (3)O12—C131.458 (3)
C2—O31.428 (3)C13—C141.505 (3)
C2—C171.508 (4)C13—H1310.989
C2—C181.496 (4)C14—O151.417 (3)
O3—C41.433 (3)C14—H1410.983
C4—C51.544 (3)C14—H1420.987
C4—C131.518 (3)O15—H1510.837
C4—H410.993C16—H1610.977
C5—C61.512 (3)C16—H1620.972
C5—H510.985C16—H1630.969
C6—N71.486 (3)C17—H1720.967
C6—C101.538 (3)C17—H1710.976
C6—C161.533 (3)C17—H1730.981
N7—N81.238 (3)C18—H1820.981
N8—N91.136 (3)C18—H1810.972
C10—O111.203 (3)C18—H1830.969
C2—O1—C5106.47 (18)C4—C13—O12111.08 (19)
O1—C2—O3103.17 (18)C4—C13—C14114.0 (2)
O1—C2—C17110.9 (2)O12—C13—C14106.09 (19)
O3—C2—C17110.6 (2)C4—C13—H131109.0
O1—C2—C18107.4 (2)O12—C13—H131108.6
O3—C2—C18109.4 (2)C14—C13—H131108.0
C17—C2—C18114.7 (2)C13—C14—O15111.0 (2)
C2—O3—C4109.49 (17)C13—C14—H141107.5
O3—C4—C5104.14 (19)O15—C14—H141109.0
O3—C4—C13109.17 (18)C13—C14—H142109.6
C5—C4—C13113.14 (19)O15—C14—H142110.1
O3—C4—H41109.8H141—C14—H142109.7
C5—C4—H41111.0C14—O15—H151107.9
C13—C4—H41109.5C6—C16—H161108.1
C4—C5—O1103.26 (17)C6—C16—H162110.0
C4—C5—C6113.20 (19)H161—C16—H162109.8
O1—C5—C6108.46 (18)C6—C16—H163110.5
C4—C5—H51110.9H161—C16—H163109.9
O1—C5—H51110.7H162—C16—H163108.6
C6—C5—H51110.1C2—C17—H172108.4
C5—C6—N7105.21 (19)C2—C17—H171108.1
C5—C6—C10108.20 (19)H172—C17—H171110.3
N7—C6—C10108.84 (18)C2—C17—H173108.3
C5—C6—C16111.2 (2)H172—C17—H173110.7
N7—C6—C16109.39 (19)H171—C17—H173111.0
C10—C6—C16113.6 (2)C2—C18—H182108.8
C6—N7—N8114.5 (2)C2—C18—H181109.6
N7—N8—N9172.4 (3)H182—C18—H181110.4
C6—C10—O11123.4 (2)C2—C18—H183108.6
C6—C10—O12116.6 (2)H182—C18—H183110.0
O11—C10—O12120.0 (2)H181—C18—H183109.4
C10—O12—C13119.50 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H51···O15i0.992.283.141 (4)146
C13—H131···O11ii0.992.573.473 (4)152
C16—H161···O11iii0.982.463.333 (4)149
C16—H163···O11ii0.972.543.465 (4)159
O15—H151···O1iv0.842.142.930 (4)157
O15—H151···N7iv0.842.523.072 (4)125
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x+1, y, z; (iii) x+1/2, y+3/2, z+1; (iv) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC10H15N3O5
Mr257.25
Crystal system, space groupOrthorhombic, P212121
Temperature (K)150
a, b, c (Å)5.9481 (3), 13.3427 (7), 15.6351 (9)
V3)1240.86 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.20 × 0.15 × 0.05
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.89, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections
10775, 1647, 1170
Rint0.077
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.087, 0.88
No. of reflections1647
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.45

Computer programs: COLLECT (Nonius, 2001)., DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O15—H151···O1i0.842.142.930 (4)157
O15—H151···N7i0.842.523.072 (4)125
Symmetry code: (i) x+1, y1/2, z+3/2.
 

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
First citationBaird, P. D., Dho, J. C., Fleet, G. W. J., Peach, J. M., Prout, K. & Smith, P. W. (1987). J. Chem. Soc. Perkin Trans. 1, pp. 1785–1791.  CSD CrossRef Web of Science Google Scholar
First citationBetteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  Web of Science CrossRef IUCr Journals Google Scholar
First citationBooth, K. V., da Cruz, F. P., Hotchkiss, D. J., Jenkinson, S. F., Jones, N. A., Weymouth-Wilson, A. C., Clarkson, R., Heinz, T. & Fleet, G. W. J. (2008). Tetrahedron: Asymmetry, 19, 2417–2424.  Web of Science CrossRef CAS Google Scholar
First citationBooth, K. V., Watkin, D. J., Jenkinson, S. F. & Fleet, G. W. J. (2007). Acta Cryst. E63, o1759–o1760.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruce, I., Fleet, G. W. J., Girdhar, A., Haraldsson, M., Peach, J. M. & Watkin, D. J. (1990). Tetrahedron, 46, 19–32.  CSD CrossRef CAS Web of Science Google Scholar
First citationChesterton, A. K. S., Jenkinson, S. F., Jones, N. A., Fleet, G. W. J. & Watkin, D. J. (2006). Acta Cryst. E62, o2983–o2985.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationCruz, F. P. da, Horne, G. & Fleet, G. W. J. (2008). Tetrahedron Lett. 49, 6812–6815.  Google Scholar
First citationFechter, M. H., Stutz, A. E. & Tauss, A. (1999). Curr. Org. Chem. 3, 269–285.  CAS Google Scholar
First citationFleet, G. W. J. (1989). Chem. Br. 25, 287–291.  CAS Google Scholar
First citationHotchkiss, D. J., Jenkinson, S. F., Booth, K. V., Fleet, G. W. J. & Watkin, D. J. (2007). Acta Cryst. E63, o2168–o2170.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHotchkiss, D. J., Kato, A., Odell, B., Claridge, T. D. W. & Fleet, G. W. J. (2007). Tetrahedron Asymmetry, 18, 500–512.  Web of Science CrossRef CAS Google Scholar
First citationJones, N. A., Rao, D., Yoshihara, A., Gullapalli, P., Morimoto, K., Takata, G., Hunter, S. J., Wormald, M. R., Dwek, R. A., Izumori, K. & Fleet, G. W. J. (2008). Tetrahedron Asymmetry, 19, 1904–1918.  Web of Science CrossRef CAS Google Scholar
First citationLarson, A. C. (1970). Crystallographic Computing, Edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard.  Google Scholar
First citationLichtenthaler, F. W. & Peters, S. (2004). C. R. Chim. 7, 65–90.  Web of Science CrossRef CAS Google Scholar
First citationNonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationPunzo, F., Watkin, D. J., Jenkinson, S. F., Cruz, F. P. & Fleet, G. W. J. (2005). Acta Cryst. E61, o511–o512.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRao, D., Yoshihara, A., Gullapalli, P., Morimoto, K., Takata, G., da Cruz, F. P., Jenkinson, S. F., Wormald, M. R., Dwek, R. A., Fleet, G. W. J. & Izumori, K. (2008). Tetrahedron Lett. 49, 3316–3121.  Web of Science CrossRef CAS Google Scholar
First citationSoengas, R., Izumori, K., Simone, M. I., Watkin, D. J., Skytte, U. P., Soetaert, W. & Fleet, G. W. J. (2005). Tetrahedron Lett. 46, 5755–5759.  Web of Science CrossRef CAS Google Scholar
First citationWatkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.  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
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds