PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3156–o3157.
Published online 2010 November 13. doi:  10.1107/S1600536810045332
PMCID: PMC3011485

2-Amino-1-(2-carboxyl­atoeth­yl)pyrimidin-1-ium monohydrate

Abstract

In the title structure, C7H9N3O2·H2O, there are two formula units in the asymmetric unit. The mol­ecule is a zwitterion, containing a quaternary N atom and a deprotonated carboxyl group, with C—O distances in the range 1.256 (2)–1.266 (3) Å. The two independent mol­ecules form a hydrogen-bonded R 2 2(16) dimer about an approximate inversion center via N—H(...)O hydrogen bonds, with N(...)O distances of 2.766 (2) and 2.888 (2) Å. O—H(...)O hydro­gen bonds involving the water mol­ecules and additional N—H(...)O hydrogen bonds link these dimers, forming double chains.

Related literature

For background information on deep eutectic solvents, see: Abbott et al. (2003 [triangle], 2004 [triangle]); Reddy (2006 [triangle]); Santos et al. (2007 [triangle]); Walker et al. (2004 [triangle]). For graph sets, see: Etter (1990 [triangle]). For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). For related structures, see: Holy et al. (1999 [triangle]); Slouf et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3156-scheme1.jpg

Experimental

Crystal data

  • C7H9N3O2·H2O
  • M r = 185.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3156-efi1.jpg
  • a = 10.075 (2) Å
  • b = 15.576 (5) Å
  • c = 10.810 (3) Å
  • β = 107.741 (16)°
  • V = 1615.7 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 90 K
  • 0.17 × 0.12 × 0.05 mm

Data collection

  • Nonius KappaCCD diffractometer with Oxford Cryostream cooler
  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 [triangle]) T min = 0.980, T max = 0.994
  • 10202 measured reflections
  • 3518 independent reflections
  • 2418 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.119
  • S = 1.02
  • 3518 reflections
  • 260 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045332/pv2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045332/pv2345Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This research was made possible by a grant supplied by the National Science Foundation’s Early CAREER program (Cooperative Agreement DMR-0449886) at Southern University. The purchase of the NMR was made possible by the National Science Foundation’s Major Research Instrument program (Cooperative Agreement CHE-0321591) at Southern University. The purchase of the FTIR was made possible by grant No. LEQSF(2005–2007)-ENH-TR-65, and the purchase of the diffractometer at LSU was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, both administered by the Louisiana Board of Regents.

supplementary crystallographic information

Comment

With the growing environmental awareness of the global economy, there has been an increased interest in "green" solvents. Since ionic liquids or ionic solvents are considered nonvolatile substances with negligible vapor pressure, they can be utilized in establishing novel "green" synthetic routes (Santos et al., 2007). Deep eutectic solvents (DES) are considered a designated group within the broad range of ionic solvents, more specifically, they are a type of ionic solvent with special properties composed of a mixture that forms a eutectic with a melting point much lower than either of the individual components. The first generation eutectic solvents were based on mixtures of quaternary ammonium salts with hydrogen donors such as amines and carboxylic acids. The deep eutectic solvent concept was first described by Abbot et al. (2003, 2004) for a mixture of choline chloride and urea. The mixture resulted in a eutectic that melts at 285 K.

DES are capable of dissolving many metal salts. Since the solvents are conductive, DES have a potential application as battery electrolytes. Compared to ionic liquids, deep eutectic solvents are cheaper to make, much less toxic, and are sometimes biodegradable. Production of 3-(2-aminopyrimidin-1-yl) propanoate by quaternerization of the amine within the aromatic system presents a new molecular construct for deep eutectic solvents. DES can be modified in order to control factors such as conductivity, viscosity, and surface tension (Reddy, 2006). The synthesis of of 3-(2-aminopyrimidin-1-yl) propanoate takes advantage of the self-initiating condensation of 2-aminopyrimidine with the vinyl group of the αβ-unsaturated acrylic acid via anti-Markovnikov addition, which is similar to chemistry involved in the synthesis of the novel 3,3',3"-nitrilotripropionic acid precursor gel, that we have recently developed (Walker et al., 2004).

The asymmetric unit of the title compound, consisting of two 2-aminopyrimidinium carboxylate molecules and two water molecules, is shown in Fig. 1. The two main molecules form a hydrogen-bonded dimer of graph set (Etter, 1990) R22(16) about an approximate inversion center located near 0.186, 0.632, 0.281. The carboxyl group is deprotonated, as evidenced by all C—O distances falling within a narrow range 1.256 (2) - 1.266 (3) Å. The propionate side chains are extended, with N—C—C—C torsion angles 179.52 (17)° about C5—C6 and -175.40 (17)° about C12—C13. The 18-membered hydrogen-bonded rings are linked by centrosymmetric R44(12) rings involving both H atoms on N3 and both O atoms O3 and O4 of the same carboxylate, as can been seen in the unit-cell diagram, Figure 2. Both water molecules link the 18-membered rings via O—H···O hydrogen bonds, forming double chains in which N6—H···O2 (at x, 3/2 - y, z - 1/2) are also involved, as illustrated in Fig. 3.

We find no previous examples of 2-aminopyrimidine with a C atom on a ring N in the Cambridge Structural Database (Allen, 2002, version 5.31, Nov. 2009), although there are a few examples of N—-C substituted 2,4-diaminopyrimidine structures (Holy et al., 1999; Slouf et al., 2002).

Experimental

2-Aminopyrimidine (1.001 g, 10.52 mmol) was dissolved in 10 ml deionized water. The solution was charged with acrylic acid (1.5 ml, 21.9 mmol) and refluxed at 343–348 K for 2 h. After heating, the mixture was stirred continuously until the temperature gradually cooled to room temperature (299 K). A light yellow aqueous slurry was obtained. In a 125 ml separatory funnel, the aqueous slurry was combined with 15 ml of benzene and shaken for several minutes. The aqueous layer was isolated and filtered. The resulting white crystalline material product was isolated by gravimetric filtration, washed with three 20 ml aliquots of cold ethanol, and allowed to air-dry overnight, yielding 1.217 g (69.36%) of white solid material.

Refinement

H atoms on C were placed in idealized positions with C—H distances 0.95 - 0.99 Å and thereafter treated as riding. Coordinates for the H atoms on N and H2O were refined. Uiso for H was assigned as 1.2 times Ueqof the attached atoms (1.5 for methyl and H2O).

Figures

Fig. 1.
The asymmetric unit, with ellipsoids at the 50% level and H atoms having arbitrary radius. Dotted lines are hydrogen bonds.
Fig. 2.
The unit cell.
Fig. 3.
A portion of the hydrogen-bonded double chain.

Crystal data

C7H9N3O2·H2OF(000) = 784
Mr = 185.19Dx = 1.523 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3071 reflections
a = 10.075 (2) Åθ = 2.5–27.1°
b = 15.576 (5) ŵ = 0.12 mm1
c = 10.810 (3) ÅT = 90 K
β = 107.741 (16)°Plate, colorless
V = 1615.7 (8) Å30.17 × 0.12 × 0.05 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream cooler3518 independent reflections
Radiation source: fine-focus sealed tube2418 reflections with I > 2σ(I)
graphiteRint = 0.031
ω and [var phi] scansθmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)h = −12→12
Tmin = 0.980, Tmax = 0.994k = −19→16
10202 measured reflectionsl = −13→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119w = 1/[σ2(Fo2) + (0.0416P)2 + 1.0034P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3518 reflectionsΔρmax = 0.26 e Å3
260 parametersΔρmin = −0.34 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0052 (10)

Special details

Experimental. 1H (D2O): δ(p.p.m.) 2.72 (t, 2H, J = 6.14 Hz), 4.33 (t, 2H, J = 6.14 Hz), 7.01 (t, 1H, J = 5.6 Hz), 8.32 (d, 1H, J = 5.6 Hz), and 8.69 (d, 1H, J = 5.6 Hz). 13C (D2O): δ(p.p.m.) 34.2, 51.9, 111.3, 150.5, 155.8, 166.2, and 177.5. IR (thin film, KBr plates, cm-1): 3428.76 (m, br), 3093.35 (br), 2363.8 (m), 1675.0 (m), 1386.82 (s), 1262.48 (s), 1193.82 (w, sh), 1094.27 (w), 1024.62 (w), and 931.94 (w, sh).
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.16601 (14)0.69376 (10)0.15055 (14)0.0176 (4)
O20.30612 (14)0.78552 (10)0.28952 (15)0.0188 (4)
N1−0.14185 (16)0.70633 (11)0.33727 (16)0.0135 (4)
N2−0.23793 (17)0.66797 (12)0.50401 (18)0.0161 (4)
N3−0.02988 (18)0.60908 (12)0.50172 (19)0.0159 (4)
H31N−0.036 (2)0.5803 (16)0.566 (2)0.019*
H32N0.038 (2)0.5978 (15)0.464 (2)0.019*
C1−0.1350 (2)0.66116 (13)0.4473 (2)0.0134 (4)
C2−0.3421 (2)0.72143 (14)0.4525 (2)0.0152 (5)
H2−0.41510.72500.49090.018*
C3−0.3504 (2)0.77295 (14)0.3446 (2)0.0159 (5)
H3−0.42490.81220.31120.019*
C4−0.2464 (2)0.76392 (14)0.2900 (2)0.0161 (5)
H4−0.24670.79850.21750.019*
C5−0.0369 (2)0.69512 (14)0.2672 (2)0.0143 (5)
H5A−0.08170.70580.17340.017*
H5B−0.00290.63510.27740.017*
C60.0857 (2)0.75559 (14)0.3174 (2)0.0164 (5)
H6A0.12980.74520.41130.020*
H6B0.05160.81560.30650.020*
C70.1944 (2)0.74413 (14)0.2470 (2)0.0142 (5)
O30.20974 (14)0.56176 (10)0.42323 (14)0.0169 (3)
O40.07476 (14)0.47312 (10)0.27549 (14)0.0175 (4)
N40.51826 (16)0.56177 (11)0.22871 (16)0.0132 (4)
N50.58362 (17)0.58906 (12)0.03946 (17)0.0159 (4)
N60.37231 (18)0.63627 (12)0.05084 (19)0.0161 (4)
H61N0.362 (2)0.6558 (16)−0.025 (3)0.019*
H62N0.313 (2)0.6537 (15)0.094 (2)0.019*
C80.4900 (2)0.59599 (13)0.1067 (2)0.0137 (4)
C90.7023 (2)0.54856 (14)0.0946 (2)0.0164 (5)
H90.76850.54500.04830.020*
C100.7352 (2)0.51078 (14)0.2174 (2)0.0172 (5)
H100.82020.48070.25350.021*
C110.6406 (2)0.51888 (14)0.2830 (2)0.0169 (5)
H110.65950.49460.36720.020*
C120.4179 (2)0.56957 (14)0.3045 (2)0.0140 (5)
H12A0.37930.62850.29530.017*
H12B0.46720.55940.39760.017*
C130.2994 (2)0.50517 (14)0.2575 (2)0.0171 (5)
H13A0.33840.44640.27290.021*
H13B0.25650.51230.16270.021*
C140.1859 (2)0.51433 (14)0.3239 (2)0.0144 (5)
O1W0.42213 (16)0.65900 (11)0.59146 (17)0.0215 (4)
H11W0.359 (3)0.6329 (17)0.527 (3)0.032*
H12W0.384 (3)0.6801 (18)0.643 (3)0.032*
O2W−0.06112 (17)0.60258 (12)−0.02453 (18)0.0270 (4)
H21W0.023 (3)0.6207 (18)0.026 (3)0.040*
H22W−0.043 (3)0.5764 (19)−0.088 (3)0.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0148 (7)0.0222 (9)0.0171 (8)0.0004 (6)0.0067 (6)−0.0044 (7)
O20.0152 (7)0.0226 (9)0.0200 (9)−0.0030 (6)0.0072 (6)−0.0027 (7)
N10.0126 (8)0.0152 (9)0.0133 (10)0.0016 (7)0.0050 (7)0.0000 (8)
N20.0147 (8)0.0181 (10)0.0170 (10)−0.0001 (7)0.0070 (7)−0.0013 (8)
N30.0152 (9)0.0178 (10)0.0164 (10)0.0020 (8)0.0073 (8)0.0037 (8)
C10.0138 (9)0.0130 (11)0.0136 (11)−0.0026 (8)0.0044 (8)−0.0024 (9)
C20.0116 (9)0.0182 (12)0.0169 (12)−0.0017 (9)0.0061 (9)−0.0049 (9)
C30.0129 (10)0.0168 (12)0.0177 (12)0.0018 (8)0.0042 (9)0.0004 (9)
C40.0167 (10)0.0168 (12)0.0137 (12)0.0002 (9)0.0030 (9)−0.0010 (9)
C50.0145 (10)0.0168 (11)0.0138 (11)0.0016 (9)0.0073 (8)0.0005 (9)
C60.0153 (10)0.0163 (12)0.0186 (12)−0.0011 (9)0.0065 (9)−0.0016 (9)
C70.0158 (10)0.0150 (11)0.0127 (11)0.0019 (9)0.0056 (9)0.0047 (9)
O30.0154 (7)0.0205 (8)0.0159 (8)0.0005 (6)0.0063 (6)−0.0019 (7)
O40.0141 (7)0.0216 (9)0.0168 (8)−0.0026 (6)0.0050 (6)0.0005 (7)
N40.0123 (8)0.0142 (9)0.0143 (9)0.0001 (7)0.0057 (7)0.0010 (7)
N50.0156 (8)0.0172 (10)0.0167 (10)−0.0018 (7)0.0077 (7)−0.0012 (8)
N60.0170 (9)0.0196 (10)0.0135 (10)0.0025 (8)0.0074 (8)0.0011 (8)
C80.0138 (9)0.0118 (11)0.0163 (11)−0.0029 (8)0.0059 (8)−0.0019 (9)
C90.0134 (10)0.0187 (12)0.0183 (12)−0.0029 (9)0.0068 (9)−0.0050 (10)
C100.0134 (10)0.0169 (12)0.0202 (12)0.0003 (9)0.0037 (9)−0.0025 (9)
C110.0149 (10)0.0168 (12)0.0180 (12)−0.0019 (9)0.0035 (9)−0.0010 (9)
C120.0146 (10)0.0174 (12)0.0116 (11)0.0001 (8)0.0064 (8)−0.0013 (9)
C130.0178 (10)0.0161 (11)0.0190 (12)−0.0009 (9)0.0080 (9)−0.0032 (9)
C140.0141 (10)0.0168 (12)0.0132 (11)0.0020 (9)0.0055 (8)0.0040 (9)
O1W0.0201 (8)0.0266 (10)0.0194 (9)−0.0030 (7)0.0083 (7)−0.0066 (7)
O2W0.0221 (8)0.0396 (11)0.0215 (10)−0.0092 (8)0.0100 (7)−0.0071 (8)

Geometric parameters (Å, °)

O1—C71.266 (3)N4—C111.367 (3)
O2—C71.256 (2)N4—C81.370 (3)
N1—C41.359 (3)N4—C121.487 (2)
N1—C11.365 (3)N5—C91.322 (3)
N1—C51.487 (3)N5—C81.359 (3)
N2—C21.322 (3)N6—C81.315 (3)
N2—C11.360 (3)N6—H61N0.85 (3)
N3—C11.322 (3)N6—H62N0.90 (2)
N3—H31N0.85 (3)C9—C101.397 (3)
N3—H32N0.91 (2)C9—H90.9500
C2—C31.397 (3)C10—C111.356 (3)
C2—H20.9500C10—H100.9500
C3—C41.358 (3)C11—H110.9500
C3—H30.9500C12—C131.523 (3)
C4—H40.9500C12—H12A0.9900
C5—C61.516 (3)C12—H12B0.9900
C5—H5A0.9900C13—C141.531 (3)
C5—H5B0.9900C13—H13A0.9900
C6—C71.522 (3)C13—H13B0.9900
C6—H6A0.9900O1W—H11W0.89 (3)
C6—H6B0.9900O1W—H12W0.84 (3)
O3—C141.265 (3)O2W—H21W0.90 (3)
O4—C141.258 (2)O2W—H22W0.86 (3)
C4—N1—C1119.69 (17)C11—N4—C12118.61 (17)
C4—N1—C5118.41 (17)C8—N4—C12121.46 (16)
C1—N1—C5121.90 (17)C9—N5—C8118.44 (19)
C2—N2—C1118.38 (19)C8—N6—H61N116.1 (16)
C1—N3—H31N116.4 (16)C8—N6—H62N123.7 (15)
C1—N3—H32N121.7 (15)H61N—N6—H62N119 (2)
H31N—N3—H32N121 (2)N6—C8—N5117.9 (2)
N3—C1—N2117.7 (2)N6—C8—N4121.43 (18)
N3—C1—N1121.68 (18)N5—C8—N4120.66 (18)
N2—C1—N1120.64 (18)N5—C9—C10123.34 (19)
N2—C2—C3123.45 (19)N5—C9—H9118.3
N2—C2—H2118.3C10—C9—H9118.3
C3—C2—H2118.3C11—C10—C9117.2 (2)
C4—C3—C2116.5 (2)C11—C10—H10121.4
C4—C3—H3121.8C9—C10—H10121.4
C2—C3—H3121.8C10—C11—N4120.4 (2)
C3—C4—N1121.1 (2)C10—C11—H11119.8
C3—C4—H4119.4N4—C11—H11119.8
N1—C4—H4119.4N4—C12—C13110.99 (17)
N1—C5—C6111.90 (17)N4—C12—H12A109.4
N1—C5—H5A109.2C13—C12—H12A109.4
C6—C5—H5A109.2N4—C12—H12B109.4
N1—C5—H5B109.2C13—C12—H12B109.4
C6—C5—H5B109.2H12A—C12—H12B108.0
H5A—C5—H5B107.9C12—C13—C14113.84 (18)
C5—C6—C7112.33 (18)C12—C13—H13A108.8
C5—C6—H6A109.1C14—C13—H13A108.8
C7—C6—H6A109.1C12—C13—H13B108.8
C5—C6—H6B109.1C14—C13—H13B108.8
C7—C6—H6B109.1H13A—C13—H13B107.7
H6A—C6—H6B107.9O4—C14—O3124.47 (19)
O2—C7—O1124.89 (19)O4—C14—C13117.05 (19)
O2—C7—C6117.22 (19)O3—C14—C13118.48 (18)
O1—C7—C6117.88 (18)H11W—O1W—H12W110 (2)
C11—N4—C8119.92 (17)H21W—O2W—H22W104 (2)
C2—N2—C1—N3178.36 (19)C9—N5—C8—N6−179.88 (19)
C2—N2—C1—N1−2.2 (3)C9—N5—C8—N40.0 (3)
C4—N1—C1—N3−175.13 (19)C11—N4—C8—N6178.78 (19)
C5—N1—C1—N34.3 (3)C12—N4—C8—N6−0.8 (3)
C4—N1—C1—N25.4 (3)C11—N4—C8—N5−1.1 (3)
C5—N1—C1—N2−175.12 (18)C12—N4—C8—N5179.27 (18)
C1—N2—C2—C3−1.6 (3)C8—N5—C9—C101.5 (3)
N2—C2—C3—C42.1 (3)N5—C9—C10—C11−1.8 (3)
C2—C3—C4—N11.2 (3)C9—C10—C11—N40.6 (3)
C1—N1—C4—C3−4.9 (3)C8—N4—C11—C100.8 (3)
C5—N1—C4—C3175.6 (2)C12—N4—C11—C10−179.63 (19)
C4—N1—C5—C690.1 (2)C11—N4—C12—C13−101.4 (2)
C1—N1—C5—C6−89.4 (2)C8—N4—C12—C1378.2 (2)
N1—C5—C6—C7179.52 (17)N4—C12—C13—C14−175.40 (17)
C5—C6—C7—O2−173.50 (18)C12—C13—C14—O4168.71 (18)
C5—C6—C7—O16.4 (3)C12—C13—C14—O3−11.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H31N···O4i0.85 (3)2.05 (3)2.882 (3)170 (2)
N3—H32N···O30.91 (2)1.99 (2)2.888 (2)166 (2)
N6—H61N···O2ii0.85 (3)2.12 (3)2.960 (3)170 (2)
N6—H62N···O10.90 (2)1.88 (2)2.766 (2)169 (2)
O1W—H11W···O30.89 (3)1.93 (3)2.794 (2)165 (3)
O1W—H12W···O2iii0.84 (3)2.04 (3)2.867 (2)170 (3)
O2W—H21W···O10.90 (3)2.00 (3)2.863 (2)159 (2)
O2W—H22W···O4iv0.86 (3)2.10 (3)2.923 (2)159 (3)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2345).

References

  • Abbott, A. P., Boothby, D., Capper, G., Davies, D. L. & Rasheed, R. K. (2004). J. Am. Chem. Soc.126, 9142–9147. [PubMed]
  • Abbott, A. P., Capper, G., Davies, D. L., Rasheed, R. K. & Tambyrajah, V. (2003). Chem. Commun. pp. 70–71. [PubMed]
  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Etter, M. C. (1990). Acc. Chem. Res.23, 120–126.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Holy, A., Budesinski, M., Podlaha, J. & Cisarova, I. (1999). Collect. Czech. Chem. Commun.84, 242–256.
  • Nonius (2000). COLLECT Nonius BV, Delft, The Netherlands.
  • 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.
  • Reddy, R. G. (2006). J. Phase Equil. Diffusion, 27, 210–211.
  • Santos, L. M. N. B. F., Lopes, J. N. C., Coutinho, J. A. P., Esperanca, J. M. S. S., Gomes, L. R., Marrucho, I. M. & Rebelo, L. P. N. (2007). J. Am. Chem. Soc.129, 284–285. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Slouf, M., Holy, A., Petříček, V. & Cisarova, I. (2002). Acta Cryst. B58, 519–529. [PubMed]
  • Walker, E. H. Jr, Apblett, A. W., Walker, R. & Zachary, A. (2004). Chem. Mater.16, 5336–5343.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography