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 9| September 2010| Page o2266
https://doi.org/10.1107/S1600536810031119

5-(Hy­dr­oxy­meth­yl)furan-2-carbaldehyde

Tamila Shalumovaa and Joseph M. Tanskia*

aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
*Correspondence e-mail: jotanski@vassar.edu

(Received 26 July 2010; accepted 3 August 2010; online 11 August 2010)

The title compound (HMF), C6H6O3, is one of the products of acid-catalyzed dehydration of high-fructose corn syrup, and has been shown to be toxic to honey bees. The compound was crystallized at 276 K, and it was found that the two independent mol­ecules in the asymmetric unit form an infinite O—H⋯O hydrogen-bonding chain that is linked into a three-dimensional network structure by weak inter­molecular C—H⋯O contacts.

Related literature

For the formation of HMF from high-fructose corn syrup, see: Le Blanc et al. (2009[Le Blanc, B. W., Eggleston, G., Sammataro, D., Cornett, C., Dufault, R., Deeby, T. & St Cyr, E. (2009). J. Agric. Food Chem. 57, 7369-7376.]), and the story subsequently reported in Chemical & Engineering News by Kemsley (2009[Kemsley, J. N. (2009). Chem. Eng. News, 87, 37.]). The effect of HMF on honey bees was studied by Bailey (1966[Bailey, L. (1966). J. Apic. Res. 5, 127-136.]); for the mechanism of HMF formation from sugars, see: Antal et al. (1990[Antal, M. J. Jr, Mok, W. S. & Richards, G. N. (1990). Carbohydr. Res. 199, 91-109.]); Haworth & Jones (1944[Haworth, W. N. & Jones, W. G. M. (1944). J. Chem. Soc. pp. 667-670.]); Ermolaeva & Sapronova (1982[Ermolaeva, G. A. & Sapronova, L. A. (1982). Sakh. Prom-st. pp. 31-32.]). For the effect of HMF on DNA, see: Durling et al. (2009[Durling, L. J. K., Busk, L. & Hellman, B. E. (2009). Food Chem. Toxicol. 47, 880-884.]).

[Scheme 1]

Experimental

Crystal data

  • C6H6O3

  • Mr = 126.11

  • Monoclinic, P 21 /c

  • a = 15.9126 (17) Å

  • b = 5.6166 (6) Å

  • c = 13.1722 (14) Å

  • β = 90.770 (2)°

  • V = 1177.2 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 125 K

  • 0.22 × 0.19 × 0.14 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. BrukerAXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.984

  • 15720 measured reflections

  • 2933 independent reflections

  • 2246 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.089

  • S = 1.04

  • 2933 reflections

  • 169 parameters

  • 2 restraints

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

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O13—H13O⋯O23i 0.85 (1) 1.89 (1) 2.7341 (13) 175 (2)
O23—H23O⋯O11ii 0.84 (1) 1.87 (1) 2.7006 (14) 173 (2)
C14—H14A⋯O13iii 0.95 2.41 3.3029 (17) 156
C21—H21A⋯O21iv 0.95 2.56 3.4726 (15) 160
C23—H23B⋯O21iii 0.95 2.38 3.3258 (16) 175
C24—H24A⋯O23iii 0.95 2.46 3.3734 (16) 160
C26—H26A⋯O21v 0.99 2.53 3.4639 (16) 158
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z; (iii) x, y+1, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. BrukerAXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. BrukerAXS 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: 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810031119/si2283sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031119/si2283Isup2.hkl

checkCIF report


Comment top

5-(Hydroxymethyl)-2-furancarboxaldehyde (Scheme 1), or, as it is more commonly referred to as 5-hydroxymethylfurfural, HMF, is formed by acid-catalyzed dehydration of sugars, most notably of D-fructose (Antal et al., 1990; Bailey, 1966; Ermolaeva & Sapronova, 1982; Haworth & Jones, 1944). It is present in many foods such as dried fruit, coffee, and bread, and especially in food that has been heated (Durling et al., 2009). HMF is also formed by acid-catalyzed degradation of high-fructose corn syrup that has been subject to heat. It is toxic to honey bees, which are fed high-fructose corn syrup by beekeepers to promote colony growth and when nectar sources are scarce (Kemsley, 2009; Le Blanc et al., 2009). The toxicity presents itself to bees as intestinal ulcerations, which lead to dysentery and, soon after, death. One study by Durling et al., (2009) has shown that HMF may damage DNA.

The asymmetric unit contains two independent unique molecules of HMF (Figure 1) which are hydrogen bonded into an infinite one-dimensional screw-like chain along the crystallographic b axis (Figure 2, Table 1). The hydroxymethyl oxygen O23 is both a hydrogen bond donor and acceptor. The aldehyde oxygen of one of the independent molecules, O11, acts as a hydrogen bond acceptor from the proton on O23 of the second independent molecule, D···A 2.701 (1) Å. The proton on the hydroxylmethyl oxygen of the first independent molecule, O13, acts as a hydrogen bond donor to the hydroxymethyl oxygen O23, D···A 2.734 (1) Å. The aldehyde oxygen of the second molecule, O21, is not involved in classical hydrogen bonding, however it is involved in C—H···O interactions. Five weak intermolecular C—H···O contacts (Table 1) link the screw-like hydrogen bonded chains into a three-dimensional network structure.

Related literature top

For the formation of HMF from high-fructose corn syrup, see: Le Blanc et al. (2009), and the story subsequently reported in Chemical & Engineering News by Kemsley (2009). The effect of HMF on honey bees was studied by Bailey (1966); for the mechanism of HMF formation from sugars, see: Antal et al. (1990); Haworth & Jones (1944); Ermolaeva & Sapronova (1982). For the effect of HMF on DNA, see: Durling et al. (2009).

Experimental top

5-Hydroxymethylfurfural was purchased from Aldrich and used without further purification. The compound was placed in a 276 K cold room until crystallization occurred. A crystal suitable for diffraction was selected and mounted in a nylon loop with Paratone-N cryoprotectant oil with a microscope in the cold room before being placed immediately in a 125 K coldstream on the diffractometer.

Refinement top

A suitable crystal was mounted in a nylon loop with Paratone-N cryoprotectant oil and data was collected on a Bruker APEXII CCD platform diffractometer. The structure was solved using direct methods and standard difference map techniques, and was refined by full-matrix least-squares procedures on F2 with SHELXTL Version 6.14 (Sheldrick, 2008). All non-hydrogen atoms were refined anisotropically. Hydrogen atoms on carbon were included in calculated positions with distances C—H = 0.95 - 0.99 Å and were refined using a riding model, with Uiso(H) = 1.2Ueq(C). Hydrogen atoms on oxygen were refined semifreely with the help of a distance restraint d(O–H) = 0.84 Å, and Uiso(H) = 1.2Ueq(O).The extinction parameter (EXTI) refined to zero and was removed from the refinement.

Structure description top

N/A

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the two independent moleucles of HMF, with displacement ellipsoids shown at the 50% probability level. H atoms on carbon, except for the H atoms on the aldehydes, have been omitted for clarity.
[Figure 2] Fig. 2. A view of the one-dimensional hydrogen bonding chain formed by the two independent moleucles of HMF. H atoms on carbon have been omitted for clarity.
5-(Hydroxymethyl)furan-2-carbaldehyde top
Crystal data top
C6H6O3F(000) = 528
Mr = 126.11Dx = 1.423 Mg m−3
Monoclinic, P21/cMelting point = 301–307 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.9126 (17) ÅCell parameters from 5970 reflections
b = 5.6166 (6) Åθ = 2.6–28.2°
c = 13.1722 (14) ŵ = 0.12 mm−1
β = 90.770 (2)°T = 125 K
V = 1177.2 (2) Å3Block, colourless
Z = 80.22 × 0.19 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer		2933 independent reflections
Radiation source: fine-focus sealed tube2246 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −21→21
Tmin = 0.975, Tmax = 0.984k = −7→7
15720 measured reflectionsl = −17→17
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0367P)2 + 0.3118P]
where P = (Fo2 + 2Fc2)/3
2933 reflections(Δ/σ)max = 0.001
169 parametersΔρmax = 0.25 e Å−3
2 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C6H6O3V = 1177.2 (2) Å3
Mr = 126.11Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.9126 (17) ŵ = 0.12 mm−1
b = 5.6166 (6) ÅT = 125 K
c = 13.1722 (14) Å0.22 × 0.19 × 0.14 mm
β = 90.770 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		2933 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		2246 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.984Rint = 0.042
15720 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0362 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.25 e Å−3
2933 reflectionsΔρmin = −0.21 e Å−3
169 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O111.11183 (6)0.07149 (19)0.62286 (8)0.0320 (2)
O120.94229 (6)0.19067 (16)0.61025 (7)0.0227 (2)
O130.77247 (6)0.02624 (17)0.68104 (8)0.0268 (2)
H13O0.7607 (10)0.125 (3)0.7278 (11)0.032*
O210.44841 (6)−0.14117 (17)0.33477 (7)0.0259 (2)
O220.38382 (5)0.01084 (15)0.52416 (6)0.01771 (19)
O230.25895 (6)−0.14054 (16)0.67299 (7)0.0229 (2)
H23O0.2152 (9)−0.064 (3)0.6587 (12)0.027*
C111.08966 (9)0.2796 (3)0.63013 (10)0.0278 (3)
H11A1.13210.39660.64010.033*
C121.00405 (9)0.3586 (2)0.62456 (10)0.0246 (3)
C130.96973 (10)0.5808 (3)0.62951 (10)0.0295 (3)
H13B0.99890.72690.63860.035*
C140.88169 (10)0.5496 (3)0.61829 (10)0.0290 (3)
H14A0.84020.67130.61890.035*
C150.86787 (8)0.3121 (2)0.60650 (10)0.0230 (3)
C160.79019 (9)0.1669 (3)0.59398 (10)0.0271 (3)
H16A0.74210.27430.58010.032*
H16B0.79640.06080.53450.032*
C210.44388 (8)0.0692 (2)0.35668 (10)0.0209 (3)
H21A0.46420.18030.30850.025*
C220.41029 (7)0.1641 (2)0.44951 (9)0.0187 (3)
C230.39749 (8)0.3945 (2)0.47805 (10)0.0220 (3)
H23B0.41110.53340.44050.026*
C240.35976 (8)0.3853 (2)0.57519 (10)0.0235 (3)
H24A0.34230.51720.61490.028*
C250.35344 (8)0.1518 (2)0.60018 (9)0.0186 (3)
C260.32435 (8)0.0284 (2)0.69336 (10)0.0215 (3)
H26A0.3726−0.05460.72570.026*
H26B0.30370.14860.74200.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0247 (5)0.0384 (6)0.0327 (6)0.0042 (4)−0.0022 (4)0.0009 (5)
O120.0223 (5)0.0214 (5)0.0244 (5)0.0033 (4)−0.0016 (4)−0.0015 (4)
O130.0294 (5)0.0216 (5)0.0294 (5)0.0024 (4)0.0051 (4)−0.0041 (4)
O210.0299 (5)0.0234 (5)0.0244 (5)0.0013 (4)0.0036 (4)−0.0020 (4)
O220.0193 (4)0.0157 (4)0.0182 (4)0.0001 (3)0.0023 (3)0.0005 (3)
O230.0216 (5)0.0214 (5)0.0258 (5)0.0011 (4)0.0041 (4)0.0035 (4)
C110.0283 (7)0.0353 (8)0.0198 (7)−0.0048 (6)−0.0006 (5)−0.0007 (6)
C120.0294 (7)0.0252 (7)0.0191 (6)−0.0038 (5)0.0012 (5)−0.0004 (5)
C130.0409 (8)0.0235 (7)0.0244 (7)−0.0023 (6)0.0079 (6)−0.0018 (6)
C140.0377 (8)0.0245 (7)0.0251 (7)0.0083 (6)0.0092 (6)0.0022 (6)
C150.0264 (7)0.0251 (7)0.0176 (6)0.0081 (5)0.0022 (5)0.0011 (5)
C160.0254 (7)0.0320 (8)0.0238 (7)0.0056 (6)−0.0001 (5)−0.0014 (6)
C210.0186 (6)0.0233 (7)0.0210 (6)0.0006 (5)0.0012 (5)0.0037 (5)
C220.0162 (6)0.0192 (6)0.0206 (6)−0.0014 (5)0.0007 (5)0.0039 (5)
C230.0221 (6)0.0175 (6)0.0263 (7)0.0003 (5)0.0008 (5)0.0029 (5)
C240.0241 (7)0.0193 (6)0.0273 (7)0.0024 (5)0.0024 (5)−0.0026 (5)
C250.0164 (6)0.0194 (6)0.0200 (6)0.0019 (5)0.0003 (5)−0.0020 (5)
C260.0215 (6)0.0233 (6)0.0197 (6)0.0011 (5)0.0013 (5)−0.0014 (5)
Geometric parameters (Å, º) top
O11—C111.2249 (18)C14—C151.360 (2)
O12—C151.3670 (15)C14—H14A0.9500
O12—C121.3732 (16)C15—C161.488 (2)
O13—C161.4239 (17)C16—H16A0.9900
O13—H13O0.850 (13)C16—H16B0.9900
O21—C211.2188 (16)C21—C221.4431 (17)
O22—C251.3698 (14)C21—H21A0.9500
O22—C221.3769 (14)C22—C231.3639 (18)
O23—C261.4312 (16)C23—C241.4217 (19)
O23—H23O0.838 (13)C23—H23B0.9500
C11—C121.434 (2)C24—C251.3561 (18)
C11—H11A0.9500C24—H24A0.9500
C12—C131.364 (2)C25—C261.4888 (18)
C13—C141.418 (2)C26—H26A0.9900
C13—H13B0.9500C26—H26B0.9900
C15—O12—C12106.27 (10)C15—C16—H16B109.0
C16—O13—H13O105.8 (11)H16A—C16—H16B107.8
C25—O22—C22105.96 (9)O21—C21—C22125.62 (12)
C26—O23—H23O107.5 (11)O21—C21—H21A117.2
O11—C11—C12124.46 (13)C22—C21—H21A117.2
O11—C11—H11A117.8C23—C22—O22110.37 (11)
C12—C11—H11A117.8C23—C22—C21129.96 (12)
C13—C12—O12110.41 (12)O22—C22—C21119.65 (11)
C13—C12—C11131.41 (14)C22—C23—C24106.27 (11)
O12—C12—C11118.17 (12)C22—C23—H23B126.9
C12—C13—C14106.13 (13)C24—C23—H23B126.9
C12—C13—H13B126.9C25—C24—C23106.68 (11)
C14—C13—H13B126.9C25—C24—H24A126.7
C15—C14—C13106.91 (13)C23—C24—H24A126.7
C15—C14—H14A126.5C24—C25—O22110.71 (11)
C13—C14—H14A126.5C24—C25—C26132.47 (12)
C14—C15—O12110.28 (12)O22—C25—C26116.75 (11)
C14—C15—C16133.06 (13)O23—C26—C25112.81 (10)
O12—C15—C16116.63 (11)O23—C26—H26A109.0
O13—C16—C15112.84 (11)C25—C26—H26A109.0
O13—C16—H16A109.0O23—C26—H26B109.0
C15—C16—H16A109.0C25—C26—H26B109.0
O13—C16—H16B109.0H26A—C26—H26B107.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13O···O23i0.85 (1)1.89 (1)2.7341 (13)175 (2)
O23—H23O···O11ii0.84 (1)1.87 (1)2.7006 (14)173 (2)
C14—H14A···O13iii0.952.413.3029 (17)156
C21—H21A···O21iv0.952.563.4726 (15)160
C23—H23B···O21iii0.952.383.3258 (16)175
C24—H24A···O23iii0.952.463.3734 (16)160
C26—H26A···O21v0.992.533.4639 (16)158
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC6H6O3
Mr126.11
Crystal system, space groupMonoclinic, P21/c
Temperature (K)125
a, b, c (Å)15.9126 (17), 5.6166 (6), 13.1722 (14)
β (°) 90.770 (2)
V (Å3)1177.2 (2)
Z8
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.22 × 0.19 × 0.14
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.975, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		15720, 2933, 2246
Rint0.042
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.089, 1.04
No. of reflections2933
No. of parameters169
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13O···O23i0.850 (13)1.886 (13)2.7341 (13)175.4 (16)
O23—H23O···O11ii0.838 (13)1.867 (13)2.7006 (14)173.0 (16)
C14—H14A···O13iii0.952.413.3029 (17)155.5
C21—H21A···O21iv0.952.563.4726 (15)160.4
C23—H23B···O21iii0.952.383.3258 (16)175.0
C24—H24A···O23iii0.952.463.3734 (16)160.3
C26—H26A···O21v0.992.533.4639 (16)157.6
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y−1/2, z+1/2.
 

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

First citationAntal, M. J. Jr, Mok, W. S. & Richards, G. N. (1990). Carbohydr. Res. 199, 91–109.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationBailey, L. (1966). J. Apic. Res. 5, 127–136.  CAS Google Scholar
 First citationBruker (2007). APEX2, SADABS and SAINT. BrukerAXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDurling, L. J. K., Busk, L. & Hellman, B. E. (2009). Food Chem. Toxicol. 47, 880–884.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationErmolaeva, G. A. & Sapronova, L. A. (1982). Sakh. Prom-st. pp. 31–32.  Google Scholar
 First citationHaworth, W. N. & Jones, W. G. M. (1944). J. Chem. Soc. pp. 667–670.  CrossRef Google Scholar
 First citationKemsley, J. N. (2009). Chem. Eng. News, 87, 37.  Google Scholar
 First citationLe Blanc, B. W., Eggleston, G., Sammataro, D., Cornett, C., Dufault, R., Deeby, T. & St Cyr, E. (2009). J. Agric. Food Chem. 57, 7369–7376.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  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 66| Part 9| September 2010| Page o2266
https://doi.org/10.1107/S1600536810031119
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