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 65| Part 6| June 2009| Page o1307
doi:10.1107/S1600536809017632

[1-(1-Adamantylamino)ethyl­­idene]oxonium methane­sulfonate

Robert Vícha,a* Marek Nečas,b Zuzana Kozubkováa and Milan Potáčekb

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Masaryk University in Brno, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
*Correspondence e-mail: rvicha@ft.utb.cz

(Received 4 May 2009; accepted 11 May 2009; online 20 May 2009)

In the title salt, C12H20NO+·CH3SO3−, the [1-(1-adamantyl­amino)ethyl­idene]oxonium cations and methane­sulfonate anions are linked into chains along the a axis via O—H⋯O and N—H⋯O hydrogen bonds. All non-H atoms of the acetamido group are essentially planar, with a maximum deviation of 0.0085 (12) Å. In comparison with related structures, the carbonyl C=O bond is slightly elongated [1.249 (2) Å], whereas the amide C—N bond is shortened [1.292 (2) Å].

Related literature

For previously published structures of N-(1-adamant­yl)­acetamide, see: Pröhl et al. (1997[Pröhl, H.-H., Blaschette, A. & Jones, P. G. (1997). Acta Cryst. C53, 1434-1436.]); Kashino et al. (1998[Kashino, S., Tateno, S., Hamada, N. & Haisa, M. (1998). Acta Cryst. C54, 273-274.]); Mizoguchi et al. (1997[Mizoguchi, J., Takayuki, M. & Kashino, S. (1997). Acta Cryst. C53 IUC9700024.]). For the preparation of N-(1-adaman­t­yl)­acetamide, see: Bach et al. (1979[Bach, R. D., Holubka, J. W. & Taaffee, T. A. (1979). J. Org. Chem. 44, 1739-1740.], 1980[Bach, R. D., Taaffee, T. A. & Rajan, S. J. (1980). J. Org. Chem. 45, 165-167.]); Gerzon et al. (1963[Gerzon, K., Krumalns, E. V., Brindle, R. L., Marshall, F. J. & Root, M. A. (1963). J. Med. Chem. 6, 760-763.]); Stetter et al. (1959[Stetter, H., Schwarz, M. & Hirschhorn, A. (1959). Chem. Ber. 92, 1629-1635.], 1960[Stetter, H., Mayer, J., Schwarz, M. & Wulff, K. (1960). Chem. Ber. 93, 226-230.]). For the biological activity of related adamantane derivatives, see: Davies et al. (1964[Davies, W. L., Grubery, R. R., Haff, R. F., McGahen, J. W., Neumayer, E. M., Paulshock, M., Watts, J. C., Wood, T. R., Hermann, E. C. & Hoffmann, C. E. (1964). Science, 144, 862-863.]); Aldrich et al. (1971[Aldrich, P. E., Hermann, E. C., Meier, E. E., Paulshock, M., Richard, W. W., Snyder, J. A. & Watts, J. C. (1971). J. Med. Chem. 14, 535-543.]).

[Scheme 1]

Experimental

Crystal data

  • C12H20NO+·CH3SO3−

  • Mr = 289.38

  • Orthorhombic, P b c a

  • a = 12.9848 (7) Å

  • b = 11.2625 (6) Å

  • c = 19.0037 (10) Å

  • V = 2779.1 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 120 K

  • 0.40 × 0.40 × 0.35 mm
Data collection

  • Kuma KM-4 CCD diffractometer

  • Absorption correction: multi-scan (Xcalibur; Oxford Diffraction, 2006[Oxford Diffraction (2006). Xcalibur CCD System. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.824, Tmax = 0.914

  • 19453 measured reflections

  • 2454 independent reflections

  • 2000 reflections with I > 2σ(I)

  • Rint = 0.017
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.102

  • S = 1.09

  • 2454 reflections

  • 180 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.47 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O3i 0.87 (2) 1.98 (2) 2.838 (2) 170.1 (19)
O1—H2⋯O2 0.98 (2) 1.49 (2) 2.4632 (18) 173 (2)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: Xcalibur (Oxford Diffraction, 2006[Oxford Diffraction (2006). Xcalibur CCD System. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: Xcalibur (Oxford Diffraction, 2006[Oxford Diffraction (2006). Xcalibur CCD System. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); data reduction: Xcalibur (Oxford Diffraction, 2006[Oxford Diffraction (2006). Xcalibur CCD System. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017632/pk2161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017632/pk2161Isup2.hkl

checkCIF report


Comment top

Since 1964, 1-aminoadamantane and related compounds have seen extensive examination due to their antiviral activity (Davies et al., 1964; Aldrich et al., 1971). The consecution of adamantane bromination, reaction with acetonitrile and final hydrolysis of N-(1-adamantyl)acetamide provides a viable synthetic method for 1-aminoadamantane production. The synthesis of N-(1-adamantyl)acetamide via nucleophilic substitution from varied bridgehead-substituted derivatives was previously described. For this purpose 1-iodoadamantane (Bach et al., 1980), 1-bromoadamantane (Stetter et al., 1960), 1-chloroadamantane (Gerzon et al., 1963), 1-alkoxyadamantane (Bach et al., 1979; Bach et al., 1980) or adamantan-1-ol (Stetter et al., 1959) were used as starting material. The title salt was prepared by replacement of a good-leaving group in 1-adamantyl methanesulfonate with acetonitrile.

In the structure of title salt (Fig. 1), the O-protonated N-(1-adamantyl)acetamide and methansulfonate are linked alternately into chains parallel to the a axis via O1–H2···O2 and N1–H1···O3 hydrogen bonds (Table 1, Fig. 2). All non-hydrogen atoms of the acetamido group (C11, C12, N1, O1) and C1 lie in plane with the maximum deviation from the best plane being 0.0085 (12) Å for atom N1. The distance of the H1 and H2 from the best plane (C1, C11, C12, N1, O1) is 0.004 (19) and 0.11 (2) Å respectively. In comparison with previously published structures of N-(1-adamantyl)acetamide (Pröhl et al., 1997; Kashino et al., 1998 and Mizoguchi et al. , 1997), the length of N1–C11 is slightly shorter, being 1.292 (2) Å [published 1.323 (5)–1.345 (2) Å] and C11–O1 is slightly longer at 1.294 (2) Å [published 1.230 (5)–1.237 (4) Å]. This may be attributed to enhanced electron withdrawing effect of the protonated O1.

Related literature top

For previously published structures of N-(1-adamantyl)acetamide, see: Pröhl et al. (1997); Kashino et al. (1998); Mizoguchi et al. (1997). For the preparation of N-(1-adamantyl)acetamide, see: Bach et al. (1979, 1980); Gerzon et al. (1963); Stetter et al. (1959, 1960). For the biological activity of related adamantane derivatives, see: Davies et al. (1964); Aldrich et al. (1971).

Experimental top

1-Adamantyl methansulfonate (500 mg, 2.17 mmol) was stirred in 20 ml of dry acetonitrile at room temperature for 1 h. After this period, the solution was allowed to stand at room temperature for several days and growth of crystals was observed. The solid was filtered off with suction and mother liquor was evaporated to obtain a second crop of title compound as a colourless powder. The combined yield of the title salt was 583 mg (93%). 1H NMR spectra were similar to those obtained for equimolar mixture of separately prepared N-(1-adamantyl)acetamide and methanesulfonic acid.

Refinement top

H atoms were found in difference Fourier maps. Those attached to N and O were refined while those attached to C were placed in idealized positions with constrained distances of 0.98 Å (RCH3) and 0.99 Å (R2CH2). Uiso(H) values were set to either 1.2Ueq or 1.5Ueq (RCH3, OH) of the attached atom.

Computing details top

Data collection: Xcalibur (Oxford Diffraction, 2006); cell refinement: Xcalibur (Oxford Diffraction, 2006); data reduction: Xcalibur (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP of the asymmetric unit with atoms represented as 50% probability ellipsoids. Hydrogen bonding is indicated by dashed lines.
[Figure 2] Fig. 2. Hydrogen bonded chains of alternating protonated N-(1-adamantyl)acetamide and methansulfonate parallel to the a axis.
[1-(1-Adamantylamino)ethylidene]oxonium methanesulfonate top
Crystal data top
C12H20NO+·CH3SO3−Dx = 1.383 Mg m−3
Mr = 289.38Melting point: 445 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2454 reflections
a = 12.9848 (7) Åθ = 3.1–25.0°
b = 11.2625 (6) ŵ = 0.24 mm−1
c = 19.0037 (10) ÅT = 120 K
V = 2779.1 (3) Å3Block, colourless
Z = 80.40 × 0.40 × 0.35 mm
F(000) = 1248
Data collection top
Kuma KM-4 CCD
diffractometer		2454 independent reflections
Radiation source: fine-focus sealed tube2000 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 0.06 pixels mm-1θmax = 25.0°, θmin = 3.1°
ω scansh = −15→14
Absorption correction: multi-scan
(Xcalibur; Oxford Diffraction, 2006)		k = −13→13
Tmin = 0.824, Tmax = 0.914l = −21→22
19453 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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.054P)2 + 1.529P]
where P = (Fo2 + 2Fc2)/3
2454 reflections(Δ/σ)max = 0.001
180 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.47 e Å−3
Crystal data top
C12H20NO+·CH3SO3−V = 2779.1 (3) Å3
Mr = 289.38Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.9848 (7) ŵ = 0.24 mm−1
b = 11.2625 (6) ÅT = 120 K
c = 19.0037 (10) Å0.40 × 0.40 × 0.35 mm
Data collection top
Kuma KM-4 CCD
diffractometer		2454 independent reflections
Absorption correction: multi-scan
(Xcalibur; Oxford Diffraction, 2006)		2000 reflections with I > 2σ(I)
Tmin = 0.824, Tmax = 0.914Rint = 0.017
19453 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.30 e Å−3
2454 reflectionsΔρmin = −0.47 e Å−3
180 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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1−0.09044 (13)0.28700 (14)0.34406 (9)0.0181 (4)
C2−0.00380 (13)0.22857 (15)0.30176 (9)0.0195 (4)
H2A0.06210.26980.31110.023*
H2B0.00380.14450.31620.023*
C3−0.10319 (14)0.41701 (15)0.32215 (9)0.0201 (4)
H3A−0.15940.45410.34960.024*
H3B−0.03880.46130.33170.024*
C4−0.19133 (14)0.22087 (16)0.33012 (9)0.0229 (4)
H4A−0.18460.13700.34510.027*
H4B−0.24770.25760.35760.027*
C5−0.21663 (15)0.22635 (17)0.25177 (10)0.0251 (4)
H5−0.28240.18280.24270.030*
C6−0.13002 (15)0.16913 (16)0.20928 (10)0.0262 (4)
H6A−0.14670.17240.15850.031*
H6B−0.12250.08470.22300.031*
C7−0.02922 (14)0.23530 (16)0.22322 (10)0.0225 (4)
H70.02760.19790.19540.027*
C8−0.04113 (14)0.36523 (15)0.20149 (9)0.0224 (4)
H8A−0.05670.37020.15060.027*
H8B0.02400.40840.21030.027*
C9−0.12838 (13)0.42199 (15)0.24371 (9)0.0213 (4)
H9−0.13620.50680.22910.026*
C10−0.22900 (14)0.35595 (17)0.22953 (10)0.0256 (4)
H10A−0.24610.36030.17880.031*
H10B−0.28580.39320.25640.031*
C110.00322 (13)0.32640 (15)0.45588 (9)0.0211 (4)
C120.01287 (15)0.30548 (18)0.53284 (10)0.0271 (4)
H12A0.07620.26090.54240.041*
H12B−0.04670.25990.54950.041*
H12C0.01550.38190.55750.041*
N1−0.06903 (11)0.27539 (13)0.42026 (8)0.0195 (3)
H1−0.1102 (15)0.2308 (18)0.4446 (11)0.023*
O10.06855 (10)0.39456 (12)0.42407 (6)0.0268 (3)
H20.1158 (17)0.436 (2)0.4560 (12)0.040*
S10.29158 (4)0.49446 (4)0.50332 (2)0.02087 (16)
O20.17962 (12)0.51334 (12)0.50208 (7)0.0302 (3)
O30.31512 (12)0.37147 (12)0.48779 (7)0.0342 (4)
O40.33796 (11)0.54034 (13)0.56618 (7)0.0357 (4)
C130.33885 (17)0.57840 (19)0.43323 (10)0.0356 (5)
H13A0.31910.66170.43960.053*
H13B0.30990.54850.38900.053*
H13C0.41410.57210.43180.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0179 (9)0.0183 (8)0.0179 (9)0.0002 (7)0.0006 (7)0.0014 (7)
C20.0182 (9)0.0204 (9)0.0201 (9)0.0034 (7)−0.0005 (7)−0.0017 (7)
C30.0235 (9)0.0163 (8)0.0206 (9)0.0009 (7)0.0028 (7)−0.0011 (7)
C40.0213 (9)0.0212 (9)0.0261 (10)−0.0034 (7)−0.0001 (7)0.0048 (7)
C50.0213 (9)0.0250 (10)0.0289 (10)−0.0074 (8)−0.0056 (7)0.0029 (8)
C60.0341 (11)0.0185 (9)0.0259 (10)−0.0019 (8)−0.0061 (8)−0.0019 (7)
C70.0250 (9)0.0230 (9)0.0195 (9)0.0043 (8)−0.0002 (7)−0.0037 (7)
C80.0238 (9)0.0260 (9)0.0176 (9)−0.0027 (8)−0.0004 (7)0.0002 (7)
C90.0254 (9)0.0150 (8)0.0236 (9)0.0005 (7)−0.0008 (7)0.0027 (7)
C100.0209 (9)0.0281 (10)0.0277 (10)0.0022 (8)−0.0044 (8)0.0042 (8)
C110.0207 (9)0.0209 (9)0.0216 (9)0.0041 (7)0.0029 (7)−0.0015 (7)
C120.0311 (11)0.0299 (10)0.0202 (10)0.0010 (8)−0.0021 (8)0.0001 (8)
N10.0214 (8)0.0187 (7)0.0183 (8)−0.0001 (6)0.0022 (6)0.0015 (6)
O10.0257 (7)0.0330 (7)0.0216 (7)−0.0080 (6)−0.0009 (5)−0.0008 (6)
S10.0221 (3)0.0229 (3)0.0175 (3)−0.00163 (17)−0.00125 (16)0.00108 (17)
O20.0240 (7)0.0328 (8)0.0337 (8)−0.0003 (6)0.0006 (5)−0.0114 (6)
O30.0433 (9)0.0270 (8)0.0323 (8)0.0092 (6)−0.0058 (6)0.0028 (6)
O40.0406 (8)0.0440 (8)0.0226 (7)−0.0109 (7)−0.0093 (6)0.0014 (6)
C130.0489 (13)0.0353 (11)0.0227 (10)−0.0117 (10)0.0030 (9)0.0021 (8)
Geometric parameters (Å, º) top
C1—N11.480 (2)C8—H8A0.9900
C1—C41.530 (2)C8—H8B0.9900
C1—C31.531 (2)C9—C101.527 (2)
C1—C21.531 (2)C9—H91.0000
C2—C71.530 (3)C10—H10A0.9900
C2—H2A0.9900C10—H10B0.9900
C2—H2B0.9900C11—N11.292 (2)
C3—C91.527 (2)C11—O11.294 (2)
C3—H3A0.9900C11—C121.487 (3)
C3—H3B0.9900C12—H12A0.9800
C4—C51.526 (3)C12—H12B0.9800
C4—H4A0.9900C12—H12C0.9800
C4—H4B0.9900N1—H10.87 (2)
C5—C61.527 (3)O1—H20.98 (2)
C5—C101.528 (2)S1—O41.4343 (14)
C5—H51.0000S1—O31.4489 (14)
C6—C71.529 (3)S1—O21.4695 (15)
C6—H6A0.9900S1—C131.7448 (19)
C6—H6B0.9900C13—H13A0.9800
C7—C81.528 (2)C13—H13B0.9800
C7—H71.0000C13—H13C0.9800
C8—C91.528 (2)
N1—C1—C4106.69 (13)C7—C8—H8A109.8
N1—C1—C3111.76 (14)C9—C8—H8A109.8
C4—C1—C3109.01 (14)C7—C8—H8B109.8
N1—C1—C2109.73 (14)C9—C8—H8B109.8
C4—C1—C2109.20 (14)H8A—C8—H8B108.2
C3—C1—C2110.34 (14)C3—C9—C10109.73 (14)
C7—C2—C1109.40 (14)C3—C9—C8109.77 (14)
C7—C2—H2A109.8C10—C9—C8109.74 (14)
C1—C2—H2A109.8C3—C9—H9109.2
C7—C2—H2B109.8C10—C9—H9109.2
C1—C2—H2B109.8C8—C9—H9109.2
H2A—C2—H2B108.2C9—C10—C5109.05 (14)
C9—C3—C1108.89 (14)C9—C10—H10A109.9
C9—C3—H3A109.9C5—C10—H10A109.9
C1—C3—H3A109.9C9—C10—H10B109.9
C9—C3—H3B109.9C5—C10—H10B109.9
C1—C3—H3B109.9H10A—C10—H10B108.3
H3A—C3—H3B108.3N1—C11—O1119.67 (16)
C5—C4—C1109.48 (14)N1—C11—C12120.42 (16)
C5—C4—H4A109.8O1—C11—C12119.90 (16)
C1—C4—H4A109.8C11—C12—H12A109.5
C5—C4—H4B109.8C11—C12—H12B109.5
C1—C4—H4B109.8H12A—C12—H12B109.5
H4A—C4—H4B108.2C11—C12—H12C109.5
C4—C5—C6109.89 (15)H12A—C12—H12C109.5
C4—C5—C10109.34 (15)H12B—C12—H12C109.5
C6—C5—C10109.53 (15)C11—N1—C1127.58 (15)
C4—C5—H5109.4C11—N1—H1115.2 (14)
C6—C5—H5109.4C1—N1—H1117.2 (14)
C10—C5—H5109.4C11—O1—H2113.8 (13)
C5—C6—C7109.45 (14)O4—S1—O3115.18 (9)
C5—C6—H6A109.8O4—S1—O2112.12 (8)
C7—C6—H6A109.8O3—S1—O2110.11 (8)
C5—C6—H6B109.8O4—S1—C13107.03 (9)
C7—C6—H6B109.8O3—S1—C13106.76 (9)
H6A—C6—H6B108.2O2—S1—C13104.92 (10)
C8—C7—C6109.47 (15)S1—C13—H13A109.5
C8—C7—C2109.44 (14)S1—C13—H13B109.5
C6—C7—C2109.23 (15)H13A—C13—H13B109.5
C8—C7—H7109.6S1—C13—H13C109.5
C6—C7—H7109.6H13A—C13—H13C109.5
C2—C7—H7109.6H13B—C13—H13C109.5
C7—C8—C9109.49 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.87 (2)1.98 (2)2.838 (2)170.1 (19)
O1—H2···O20.98 (2)1.49 (2)2.4632 (18)173 (2)
Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC12H20NO+·CH3SO3−
Mr289.38
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)120
a, b, c (Å)12.9848 (7), 11.2625 (6), 19.0037 (10)
V (Å3)2779.1 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.40 × 0.40 × 0.35
Data collection
DiffractometerKuma KM-4 CCD
diffractometer
Absorption correctionMulti-scan
(Xcalibur; Oxford Diffraction, 2006)
Tmin, Tmax0.824, 0.914
No. of measured, independent and
observed [I > 2σ(I)] reflections		19453, 2454, 2000
Rint0.017
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.102, 1.09
No. of reflections2454
No. of parameters180
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.30, −0.47

Computer programs: Xcalibur (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.87 (2)1.98 (2)2.838 (2)170.1 (19)
O1—H2···O20.98 (2)1.49 (2)2.4632 (18)173 (2)
Symmetry code: (i) x−1/2, −y+1/2, −z+1.
 

Acknowledgements

The financial support of this work by the Czech Ministry of Education (project No. MSM 7088352101) is gratefully acknowledged.

References

First citationAldrich, P. E., Hermann, E. C., Meier, E. E., Paulshock, M., Richard, W. W., Snyder, J. A. & Watts, J. C. (1971). J. Med. Chem. 14, 535–543.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationBach, R. D., Holubka, J. W. & Taaffee, T. A. (1979). J. Org. Chem. 44, 1739–1740.  CrossRef CAS Web of Science Google Scholar
 First citationBach, R. D., Taaffee, T. A. & Rajan, S. J. (1980). J. Org. Chem. 45, 165–167.  CrossRef CAS Web of Science Google Scholar
 First citationDavies, W. L., Grubery, R. R., Haff, R. F., McGahen, J. W., Neumayer, E. M., Paulshock, M., Watts, J. C., Wood, T. R., Hermann, E. C. & Hoffmann, C. E. (1964). Science, 144, 862–863.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGerzon, K., Krumalns, E. V., Brindle, R. L., Marshall, F. J. & Root, M. A. (1963). J. Med. Chem. 6, 760–763.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationKashino, S., Tateno, S., Hamada, N. & Haisa, M. (1998). Acta Cryst. C54, 273–274.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMizoguchi, J., Takayuki, M. & Kashino, S. (1997). Acta Cryst. C53 IUC9700024.  Google Scholar
 First citationOxford Diffraction (2006). Xcalibur CCD System. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.  Google Scholar
 First citationPröhl, H.-H., Blaschette, A. & Jones, P. G. (1997). Acta Cryst. C53, 1434–1436.  CSD CrossRef Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStetter, H., Mayer, J., Schwarz, M. & Wulff, K. (1960). Chem. Ber. 93, 226–230.  CrossRef CAS Web of Science Google Scholar
 First citationStetter, H., Schwarz, M. & Hirschhorn, A. (1959). Chem. Ber. 92, 1629–1635.  CrossRef CAS Web of Science 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 65| Part 6| June 2009| Page o1307
doi:10.1107/S1600536809017632
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