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 66| Part 8| August 2010| Page o1920
https://doi.org/10.1107/S1600536810025365

4-Hy­dr­oxy­anilinium perchlorate dihydrate

Xue-qun Fua*

aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: fuxuequn222@163.com

(Received 8 May 2010; accepted 28 June 2010; online 3 July 2010)

In the crystal structure of the title compound, C6H8NO+·ClO4−·2H2O, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds occur. The protonated amine cations and the perchlorate anions are linked through the water mol­ecules, and the hy­droxy groups of the cations and the anions are linked through the water mol­ecules. The cations are connected to the perchlorate anions via inter­molecular N—H⋯O hydrogen bonds. In addition, the crystal structure exhibits weak inter­molecular C—H⋯π inter­actions.

Related literature

For background to phase transition materials, see: Li et al. (2008[Li, X. Z., Qu, Z. R. & Xiong, R. G. (2008). Chin. J. Chem. 11, 1959-1962.]); Zhang et al. (2009[Zhang, W., Chen, L. Z., Xiong, R. G., Nakamura, T. & Huang, S. D. (2009). J. Am. Chem. Soc. 131, 12544-12545.])

[Scheme 1]

Experimental

Crystal data

  • C6H8NO+·ClO4−·2H2O

  • Mr = 245.62

  • Orthorhombic, P n a 21

  • a = 24.341 (5) Å

  • b = 5.253 (1) Å

  • c = 7.824 (2) Å

  • V = 1000.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.40 mm−1

  • T = 298 K

  • 0.40 × 0.30 × 0.20 mm
Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.866, Tmax = 0.923

  • 9517 measured reflections

  • 2275 independent reflections

  • 1986 reflections with I > 2σ(I)

  • Rint = 0.052
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.097

  • S = 1.11

  • 2275 reflections

  • 168 parameters

  • 8 restraints

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.53 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1049 Friedel pairs

  • Flack parameter: 0.00 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O⋯O2Wi 0.75 (3) 2.10 (3) 2.801 (3) 156 (4)
N1—H1N⋯O4 0.79 (5) 2.34 (5) 3.016 (4) 144 (4)
N1—H2N⋯O1Wii 0.98 (4) 1.98 (5) 2.951 (4) 168 (4)
N1—H3N⋯O1W 1.00 (5) 1.97 (5) 2.972 (4) 175 (4)
O1W—H1AW⋯O3iii 0.79 (5) 2.40 (7) 3.089 (3) 146 (8)
O1W—H1BW⋯O5 0.83 (4) 2.47 (6) 3.083 (4) 132 (5)
O2W—H2AW⋯O4 0.93 (4) 2.28 (4) 3.068 (4) 143 (4)
O2W—H2BW⋯O1iv 0.77 (3) 2.17 (3) 2.937 (3) 173 (5)
C2—H2⋯Cg1iv 0.93 2.88 3.677 (3) 144
Symmetry codes: (i) [-x+1, -y+2, z+{\script{1\over 2}}]; (ii) x, y+1, z; (iii) x, y, z+1; (iv) [-x+1, -y+1, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810025365/lx2151sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025365/lx2151Isup2.hkl

checkCIF report


Comment top

As a continuation of our study of phase transition materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009), organic–inorganic hybrids, we studied the dielectric properties of the title compound, unfortunately, there was no distinct anomaly observed from 93 K to 350 K, suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Here, we report the crystal structure of the title compound (Fig. 1).

The asymmetric unit of the title compound is made up of a 4–hydroxyanilinium cation cation wherein the non-hydrogen atoms are practically co-planar with a mean deviation of 0.015 (2) Å, a perchlorate anion and two solvent molecules of water (Fig. 1). The crystal packing (Fig. 2) is stabilized by intermolecular N—H···O , O—H···O hydrogen bonds and weak intermolecular C—H···π interactions. (Table 1). Both the protonated amine cations and the perchlorate anions are linked through the water molecules, and the hydroxy groups of the cations and the anions are linked through the water molecules. Additionally, the cations are connected to the perchlorate anions via intermolecular N—H···O hydrogen bonds.

Related literature top

For background to phase transition materials, see: Li et al. (2008); Zhang et al. (2009)

Experimental top

1.09g (10 mmol) 4–aminophenol was firstly dissolved in 10ml ethanol, to which perchloric acid aqueous solution (70% w/w) was then added under stirring until the PH of the solution was ca. 6. Ethanol was added until the precipitated substrates disappeared. Colorless prism single crystal for X–ray was obtained by the acid solution slow evaporated at room temperature after two days.

Refinement top

Aryl H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å. Uiso(H) = 1.2Ueq(C). The other H atoms attached to N and O atoms were found difference maps using restraints for O—H bond distances (O—H = 0.85 (5) Å) and H—O—H angles (H···H =1.35 (10) Å). Their displacement parameters were freely refined.

Structure description top

As a continuation of our study of phase transition materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009), organic–inorganic hybrids, we studied the dielectric properties of the title compound, unfortunately, there was no distinct anomaly observed from 93 K to 350 K, suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Here, we report the crystal structure of the title compound (Fig. 1).

The asymmetric unit of the title compound is made up of a 4–hydroxyanilinium cation cation wherein the non-hydrogen atoms are practically co-planar with a mean deviation of 0.015 (2) Å, a perchlorate anion and two solvent molecules of water (Fig. 1). The crystal packing (Fig. 2) is stabilized by intermolecular N—H···O , O—H···O hydrogen bonds and weak intermolecular C—H···π interactions. (Table 1). Both the protonated amine cations and the perchlorate anions are linked through the water molecules, and the hydroxy groups of the cations and the anions are linked through the water molecules. Additionally, the cations are connected to the perchlorate anions via intermolecular N—H···O hydrogen bonds.

For background to phase transition materials, see: Li et al. (2008); Zhang et al. (2009)

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small cycles of arbitrary radius.
[Figure 2] Fig. 2. N—H···O, O—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) - x + 1, - y + 2, z + 1/2; (ii) x, y + 1, z; (iii) x, y, z + 1; (iv) - x + 1, - y + 1, z - 1/2.]
4-Hydroxyanilinium perchlorate dihydrate top
Crystal data top
C6H8NO+·ClO4−·2H2OF(000) = 512
Mr = 245.62Dx = 1.631 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4523 reflections
a = 24.341 (5) Åθ = 3.1–55.2°
b = 5.253 (1) ŵ = 0.40 mm−1
c = 7.824 (2) ÅT = 298 K
V = 1000.4 (4) Å3Prism, colourless
Z = 40.40 × 0.30 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer		2275 independent reflections
Radiation source: fine-focus sealed tube1986 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −31→31
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −6→6
Tmin = 0.866, Tmax = 0.923l = −10→10
9517 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0423P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
2275 reflectionsΔρmax = 0.21 e Å−3
168 parametersΔρmin = −0.53 e Å−3
8 restraintsAbsolute structure: Flack (1983), 1049 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (7)
Crystal data top
C6H8NO+·ClO4−·2H2OV = 1000.4 (4) Å3
Mr = 245.62Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 24.341 (5) ŵ = 0.40 mm−1
b = 5.253 (1) ÅT = 298 K
c = 7.824 (2) Å0.40 × 0.30 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer		2275 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		1986 reflections with I > 2σ(I)
Tmin = 0.866, Tmax = 0.923Rint = 0.052
9517 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097Δρmax = 0.21 e Å−3
S = 1.11Δρmin = −0.53 e Å−3
2275 reflectionsAbsolute structure: Flack (1983), 1049 Friedel pairs
168 parametersAbsolute structure parameter: 0.00 (7)
8 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl10.70519 (2)0.26502 (10)0.38081 (9)0.03119 (16)
O10.41921 (9)0.7270 (4)0.6125 (3)0.0418 (5)
H1O0.4080 (14)0.855 (5)0.638 (4)0.041 (10)*
O20.65704 (9)0.1268 (4)0.4283 (3)0.0543 (6)
O30.72121 (12)0.1930 (5)0.2130 (3)0.0615 (7)
O40.69370 (9)0.5318 (3)0.3859 (3)0.0490 (5)
O50.74825 (10)0.2072 (4)0.4975 (4)0.0633 (7)
N10.64637 (12)0.7547 (5)0.7092 (4)0.0383 (6)
H1N0.6637 (19)0.763 (7)0.624 (7)0.067 (14)*
H2N0.6575 (16)0.911 (8)0.768 (6)0.082 (13)*
H3N0.6580 (18)0.587 (9)0.759 (6)0.102 (16)*
C10.47480 (12)0.7447 (5)0.6368 (3)0.0303 (6)
C20.50729 (12)0.5551 (5)0.5650 (4)0.0323 (6)
H20.49110.42560.50140.039*
C30.56328 (12)0.5591 (5)0.5878 (4)0.0347 (6)
H30.58520.43260.54040.042*
C40.58649 (11)0.7533 (4)0.6821 (3)0.0308 (6)
C50.55500 (11)0.9431 (5)0.7512 (4)0.0320 (6)
H50.57141.07440.81240.038*
C60.49832 (11)0.9382 (5)0.7292 (4)0.0324 (6)
H60.47651.06510.77680.039*
O1W0.68473 (10)0.2523 (4)0.8370 (3)0.0461 (6)
H1AW0.680 (3)0.245 (11)0.937 (6)0.19 (4)*
H1BW0.7155 (18)0.270 (10)0.793 (8)0.13 (2)*
O2W0.62796 (12)0.7872 (5)0.0985 (4)0.0514 (6)
H2AW0.6577 (16)0.773 (8)0.172 (5)0.079 (15)*
H2BW0.6131 (18)0.658 (6)0.103 (6)0.070 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0311 (3)0.0332 (3)0.0292 (3)0.0050 (2)0.0005 (3)−0.0030 (3)
O10.0300 (11)0.0394 (11)0.0560 (14)0.0019 (10)−0.0011 (10)−0.0022 (11)
O20.0455 (12)0.0505 (11)0.0667 (15)−0.0075 (10)0.0107 (11)0.0084 (11)
O30.0783 (17)0.0697 (15)0.0365 (14)0.0053 (14)0.0176 (13)−0.0112 (11)
O40.0573 (13)0.0358 (9)0.0541 (12)0.0082 (9)−0.0003 (13)0.0001 (11)
O50.0484 (15)0.0774 (16)0.0640 (17)0.0242 (13)−0.0244 (13)−0.0038 (13)
N10.0317 (14)0.0414 (15)0.0419 (17)0.0010 (12)0.0015 (12)0.0017 (13)
C10.0319 (14)0.0327 (13)0.0262 (14)−0.0010 (12)−0.0009 (12)0.0064 (11)
C20.0337 (15)0.0293 (13)0.0341 (14)−0.0031 (12)−0.0005 (12)−0.0067 (11)
C30.0357 (16)0.0277 (12)0.0405 (16)0.0041 (11)0.0070 (13)−0.0073 (11)
C40.0292 (13)0.0301 (13)0.0331 (14)0.0011 (12)0.0000 (11)0.0044 (11)
C50.0383 (15)0.0287 (11)0.0290 (13)−0.0009 (11)−0.0045 (12)−0.0015 (11)
C60.0358 (14)0.0295 (13)0.0320 (15)0.0087 (11)−0.0014 (11)−0.0040 (12)
O1W0.0394 (12)0.0513 (12)0.0477 (18)−0.0040 (12)−0.0053 (10)0.0005 (11)
O2W0.0401 (15)0.0486 (14)0.0654 (17)0.0015 (12)−0.0133 (12)0.0038 (13)
Geometric parameters (Å, º) top
Cl1—O31.421 (2)C2—C31.375 (4)
Cl1—O51.423 (2)C2—H20.9300
Cl1—O21.428 (2)C3—C41.379 (4)
Cl1—O41.4297 (18)C3—H30.9300
O1—C11.370 (3)C4—C51.369 (4)
O1—H1O0.75 (3)C5—C61.391 (4)
N1—C41.473 (4)C5—H50.9300
N1—H1N0.79 (5)C6—H60.9300
N1—H2N0.98 (4)O1W—H1AW0.79 (5)
N1—H3N1.00 (5)O1W—H1BW0.83 (4)
C1—C61.372 (4)O2W—H2AW0.93 (4)
C1—C21.391 (4)O2W—H2BW0.77 (3)
O3—Cl1—O5109.51 (18)C3—C2—H2120.0
O3—Cl1—O2109.27 (17)C1—C2—H2120.0
O5—Cl1—O2109.22 (16)C2—C3—C4119.1 (2)
O3—Cl1—O4109.90 (17)C2—C3—H3120.4
O5—Cl1—O4109.61 (14)C4—C3—H3120.4
O2—Cl1—O4109.31 (13)C5—C4—C3121.4 (2)
C1—O1—H1O105 (3)C5—C4—N1119.6 (2)
C4—N1—H1N114 (3)C3—C4—N1119.1 (2)
C4—N1—H2N110 (2)C4—C5—C6119.6 (2)
H1N—N1—H2N102 (4)C4—C5—H5120.2
C4—N1—H3N109 (3)C6—C5—H5120.2
H1N—N1—H3N103 (4)C1—C6—C5119.5 (2)
H2N—N1—H3N119 (4)C1—C6—H6120.2
O1—C1—C6122.4 (3)C5—C6—H6120.2
O1—C1—C2117.2 (2)H1AW—O1W—H1BW124 (7)
C6—C1—C2120.4 (3)H2AW—O2W—H2BW106 (4)
C3—C2—C1120.0 (3)
O1—C1—C2—C3−178.6 (2)C3—C4—C5—C61.3 (4)
C6—C1—C2—C30.7 (4)N1—C4—C5—C6−178.4 (3)
C1—C2—C3—C4−0.2 (4)O1—C1—C6—C5179.1 (2)
C2—C3—C4—C5−0.8 (4)C2—C1—C6—C5−0.2 (4)
C2—C3—C4—N1178.9 (3)C4—C5—C6—C1−0.8 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2Wi0.75 (3)2.10 (3)2.801 (3)156 (4)
N1—H1N···O40.79 (5)2.34 (5)3.016 (4)144 (4)
N1—H2N···O1Wii0.98 (4)1.98 (5)2.951 (4)168 (4)
N1—H3N···O1W1.00 (5)1.97 (5)2.972 (4)175 (4)
O1W—H1AW···O3iii0.79 (5)2.40 (7)3.089 (3)146 (8)
O1W—H1BW···O50.83 (4)2.47 (6)3.083 (4)132 (5)
O2W—H2AW···O40.93 (4)2.28 (4)3.068 (4)143 (4)
O2W—H2BW···O1iv0.77 (3)2.17 (3)2.937 (3)173 (5)
C2—H2···Cg1iv0.932.883.677 (3)144
Symmetry codes: (i) −x+1, −y+2, z+1/2; (ii) x, y+1, z; (iii) x, y, z+1; (iv) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formulaC6H8NO+·ClO4−·2H2O
Mr245.62
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)298
a, b, c (Å)24.341 (5), 5.253 (1), 7.824 (2)
V (Å3)1000.4 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.40
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.866, 0.923
No. of measured, independent and
observed [I > 2σ(I)] reflections		9517, 2275, 1986
Rint0.052
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.097, 1.11
No. of reflections2275
No. of parameters168
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.53
Absolute structureFlack (1983), 1049 Friedel pairs
Absolute structure parameter0.00 (7)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2Wi0.75 (3)2.10 (3)2.801 (3)156 (4)
N1—H1N···O40.79 (5)2.34 (5)3.016 (4)144 (4)
N1—H2N···O1Wii0.98 (4)1.98 (5)2.951 (4)168 (4)
N1—H3N···O1W1.00 (5)1.97 (5)2.972 (4)175 (4)
O1W—H1AW···O3iii0.79 (5)2.40 (7)3.089 (3)146 (8)
O1W—H1BW···O50.83 (4)2.47 (6)3.083 (4)132 (5)
O2W—H2AW···O40.93 (4)2.28 (4)3.068 (4)143 (4)
O2W—H2BW···O1iv0.77 (3)2.17 (3)2.937 (3)173 (5)
C2—H2···Cg1iv0.932.883.677 (3)143.9
Symmetry codes: (i) −x+1, −y+2, z+1/2; (ii) x, y+1, z; (iii) x, y, z+1; (iv) −x+1, −y+1, z−1/2.
 

Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to purchase the diffractometer.

References

First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationLi, X. Z., Qu, Z. R. & Xiong, R. G. (2008). Chin. J. Chem. 11, 1959–1962.  Web of Science CSD CrossRef Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZhang, W., Chen, L. Z., Xiong, R. G., Nakamura, T. & Huang, S. D. (2009). J. Am. Chem. Soc. 131, 12544–12545.  Web of Science CSD CrossRef PubMed CAS 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 66| Part 8| August 2010| Page o1920
https://doi.org/10.1107/S1600536810025365
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