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 70| Part 5| May 2014| Page o552
doi:10.1107/S1600536814007673

Di­ethyl 2,2′-(ethane-1,2-diyldi­­oxy)di­benzo­ate

Huaduan Shi,a Haisha Qina and Zhen Maa*

aSchool of Chemistry and Chemical Engeneering, Guangxi University, Guangxi 530004, People's Republic of China
*Correspondence e-mail: mzmz2009@sohu.com

(Received 20 March 2014; accepted 6 April 2014; online 12 April 2014)

The mol­ecular title compound, C20H22O6, was obtained by the reaction of ethyl 2-hy­droxy­benzoate with 1,2-di­chloro­ethane. The mol­ecule lies on a twofold rotation axis which passes through the middle of the central ethyl­ene bridge. This group exhibits a gauche conformation with the corresponding O—C—C—O torsion angle being 73.2 (2)°. The C atoms of the carboxyl group, the aryl and the O—CH2 group are coplanar, with an r.m.s. deviation of 0.01 Å. The two aryl rings form a dihedral angle of 67.94 (4)°. The ester ethyl group is disordered over two sets of sites with an occupancy ratio of 0.59 (2):0.41 (2). The crystal packing is dominated by van der Waals forces.

CCDC reference: 995747

Related literature

For synthesis and structures of diesters, see: Ma et al. (2012[Ma, Z., Liang, B. & Lu, W. (2012). Acta Cryst. E68, m370.]); Hou & Kan (2007[Hou, L.-M. & Kan, Y.-H. (2007). Acta Cryst. E63, o2157-o2158.]). For properties and applications of diesters, see: Chen & Liu (2002[Chen, X. & Liu, G. (2002). Chem. Eur. J. 8, 4811-4817.]). For the synthesis of the title compound, see: Ma & Liu (2002[Ma, Z. & Liu, S.-X. (2002). Chin. J. Struct. Chem. 21, 533-537.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.]). For background to the applications of organic acids and esters, see: Chanthapally et al. (2012[Chanthapally, A., Kole, G. K., Qian, K., Tan, G. K., Gao, S. & Vittal, J. J. (2012). Chem. Eur. J. 8, 7869-7877.]); Yan et al. (2012[Yan, C., Li, K., Wei, S.-C., Wang, H.-P., Fu, L., Pan, M. & Su, C.-Y. (2012). J. Mater. Chem. 22, 9846-9852.]).

[Scheme 1]

Experimental

Crystal data

  • C20H22O6

  • Mr = 358.38

  • Orthorhombic, P b c n

  • a = 21.805 (4) Å

  • b = 9.871 (2) Å

  • c = 8.8646 (18) Å

  • V = 1908.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.35 × 0.31 × 0.28 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.]) Tmin = 0.858, Tmax = 1.000

  • 11280 measured reflections

  • 2192 independent reflections

  • 1543 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.132

  • S = 1.04

  • 2192 reflections

  • 140 parameters

  • 24 restraints

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS 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

CCDC reference: 995747

Crystal structure: contains datablocks I, dierster-0. DOI: 10.1107/S1600536814007673/wm5015sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007673/wm5015Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007673/wm5015Isup3.cml

checkCIF report


Comment top

In recent years the chemistry of carboxylic compounds has been the subject of intense studies because of the potential applications of these compounds as ligands for metal complexes or of potential applications as luminescent, non-linear optical, electrical conductive and liquid-crystalline materials (Yan et al., 2012. Chanthapally et al., 2012). Esters are also very important since these compounds are commodity chemicals used as intermediates in the manufacture of acids and in the production of numerous important industrial products. Hence, the current work aims to synthesize new esters for acid production and for investigation of their coordination behaviors with metal ions (Ma et al., 2012; Chen & Liu, 2002). Here, we report the crystal structure of a new diester, C20H22O6, which was obtained by reaction of ethyl 2-hydroxybenzoate with 1,2-dichloroethane.

The structure of C20H22O6 consists of a neutral molecular unit (Fig. 1). The molecule lies on a twofold rotation axis which passes through the middle of the central ethylene bridge that has a gauche conformation with the corresponding O—C—C—O torsion angle being 73.2 (2) °. All bond lengths and angles are within normal ranges (Allen et al., 1987). The carbon atom of the carboxyl group, and the aryl and O—CH2 moeities of one half molecule are coplanar with an r.m.s. deviation of 0.01 Å. The two aryl rings form a dihedral angle of 67.94 (4) °. The ester ethyl group is disordered over two sets of sites in a 0.59 (2):0.41 (2) occupancy ratio. The packing of the molecules in the crystal structure is shown in Fig. 2.

Related literature top

For synthesis and structures of diesters, see: Ma et al. (2012); Hou & Kan (2007). For properties and applications of diesters, see: Chen & Liu (2002). For the synthesis of the title compound, see: Ma & Liu (2002). For standard bond lengths, see: Allen et al. (1987). For background to the applications of organic acids and esters, see: Chanthapally et al. (2012); Yan et al. (2012).

Experimental top

The title compound was obtained by the reaction of ethyl 2- hydroxybenzoate with 1,2-dichloroethane in N,N'- dimethylformamide (DMF) according to a reported procedure (Ma & Liu, 2002). In a 100 cm3 flask fitted with a funnel, ethyl 2- hydroxybenzoate (8.3 g, 50 mM) and potassium carbonate were mixed in 50 cm3 of DMF. To this solution was added dropwise a stoichiometric quantity of 1,2-dichloroethane (2.5 g, 25 mM) dissolved in 20 cm3 of DMF for a period of an hour under stirring. The mixture was further stirred for 24 h at 353 K. The solution was concentrated under reduced pressure and the white solid precipitated by adding a large quantity of water (200 cm3) was filtered off and recrystallized from ethanol and decolored with activated carbon. A colorless solid was finally obtained (yield 81 %, m.p: 417–419 K). Slow evaporation of a solution of the title compound in ethanol and dichloromethane (1:1) led to the formation of colorless crystals, which were suitable for X-ray characterization.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 - 0.97 Å and with Uiso(H) = 1.2 times Ueq(C) or 1.5 times Ueq (methyl C). The two carbon atoms of the ethyl group are disordered over two sets of sites with an occupancy ratio of 0.59 (2):0.41 (2). The C atoms of this group were additionally refined with the ISOR command in SHELXL.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. 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 small spheres of arbitrary radius. [symmetry code: (A) 1-x, y, 1/2-z ]
[Figure 2] Fig. 2. A view of the crystal packing along the c axis.
Diethyl 2,2'-(ethane-1,2-diyldioxy)dibenzoate top
Crystal data top
C20H22O6F(000) = 760
Mr = 358.38Dx = 1.248 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 11280 reflections
a = 21.805 (4) Åθ = 1.9–27.6°
b = 9.871 (2) ŵ = 0.09 mm−1
c = 8.8646 (18) ÅT = 298 K
V = 1908.0 (6) Å3Prism, colourless
Z = 40.35 × 0.31 × 0.28 mm
Data collection top
Bruker SMART CCD
diffractometer		2192 independent reflections
Radiation source: fine-focus sealed tube1543 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 0 pixels mm-1θmax = 27.6°, θmin = 1.9°
phi and ω scansh = −28→27
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		k = −10→12
Tmin = 0.858, Tmax = 1.000l = −10→11
11280 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0606P)2 + 0.335P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2192 reflectionsΔρmax = 0.17 e Å−3
140 parametersΔρmin = −0.14 e Å−3
24 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0102 (19)
Crystal data top
C20H22O6V = 1908.0 (6) Å3
Mr = 358.38Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 21.805 (4) ŵ = 0.09 mm−1
b = 9.871 (2) ÅT = 298 K
c = 8.8646 (18) Å0.35 × 0.31 × 0.28 mm
Data collection top
Bruker SMART CCD
diffractometer		2192 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		1543 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 1.000Rint = 0.023
11280 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04124 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.04Δρmax = 0.17 e Å−3
2192 reflectionsΔρmin = −0.14 e Å−3
140 parameters
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*/UeqOcc. (<1)
O10.36609 (7)0.94335 (11)0.09160 (14)0.0784 (4)
O20.41410 (7)0.77861 (13)−0.03024 (15)0.0880 (5)
O30.43658 (5)0.59258 (11)0.20505 (13)0.0632 (3)
C10.38057 (7)0.81417 (15)0.06775 (17)0.0570 (4)
C02A0.3859 (9)1.0477 (15)−0.0051 (11)0.075 (3)0.41 (2)
H02A0.40241.0099−0.09760.090*0.41 (2)
H02B0.35181.1066−0.03070.090*0.41 (2)
C02B0.4008 (7)1.0397 (13)−0.0105 (13)0.114 (4)0.59 (2)
H02C0.44211.0064−0.02730.137*0.59 (2)
H02D0.38041.0466−0.10740.137*0.59 (2)
C20.34747 (7)0.72278 (14)0.17329 (15)0.0522 (4)
C01A0.4309 (8)1.120 (2)0.0708 (15)0.127 (4)0.41 (2)
H01A0.41271.16830.15360.191*0.41 (2)
H01B0.44971.18350.00290.191*0.41 (2)
H01C0.46141.05870.10840.191*0.41 (2)
C01B0.4030 (7)1.1719 (7)0.0618 (8)0.119 (3)0.59 (2)
H01D0.36201.20590.07380.179*0.59 (2)
H01E0.42621.23330.00040.179*0.59 (2)
H01F0.42201.16370.15900.179*0.59 (2)
C30.28631 (8)0.74645 (17)0.20651 (18)0.0654 (4)
H3A0.26680.82150.16500.078*
C40.25382 (8)0.6610 (2)0.3000 (2)0.0766 (5)
H4A0.21260.67730.31980.092*
C50.28283 (8)0.55161 (18)0.3634 (2)0.0730 (5)
H5A0.26110.49460.42750.088*
C60.34359 (7)0.52495 (15)0.33381 (19)0.0634 (4)
H6A0.36270.45050.37780.076*
C70.37642 (7)0.60994 (14)0.23769 (16)0.0518 (4)
C80.46777 (7)0.48215 (15)0.27597 (19)0.0609 (4)
H8A0.44820.39720.24930.073*
H8B0.46620.49220.38480.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1251 (11)0.0471 (6)0.0631 (7)0.0001 (6)0.0089 (7)0.0031 (5)
O20.1222 (11)0.0685 (8)0.0732 (8)0.0098 (7)0.0363 (8)0.0084 (6)
O30.0597 (6)0.0607 (6)0.0692 (7)0.0009 (5)0.0008 (5)0.0183 (5)
C10.0753 (9)0.0505 (8)0.0451 (7)0.0019 (7)−0.0047 (7)−0.0018 (6)
C02A0.128 (7)0.054 (4)0.043 (3)−0.014 (4)−0.014 (4)0.008 (3)
C02B0.174 (9)0.065 (4)0.104 (6)−0.006 (4)0.034 (5)0.020 (4)
C20.0654 (9)0.0485 (7)0.0425 (7)−0.0015 (6)−0.0024 (6)−0.0060 (6)
C01A0.146 (10)0.103 (9)0.133 (7)−0.059 (7)0.022 (6)0.010 (7)
C01B0.228 (10)0.057 (3)0.073 (3)−0.031 (4)−0.001 (4)0.003 (2)
C30.0717 (10)0.0647 (9)0.0597 (9)0.0118 (8)0.0008 (8)−0.0057 (8)
C40.0655 (10)0.0869 (12)0.0774 (12)−0.0004 (9)0.0129 (9)−0.0070 (10)
C50.0767 (11)0.0687 (10)0.0735 (11)−0.0147 (9)0.0173 (9)0.0001 (9)
C60.0733 (10)0.0530 (8)0.0640 (9)−0.0065 (7)0.0039 (8)0.0054 (7)
C70.0580 (8)0.0487 (7)0.0488 (8)−0.0043 (6)−0.0011 (6)−0.0018 (6)
C80.0677 (8)0.0487 (8)0.0662 (9)−0.0034 (7)−0.0087 (7)0.0060 (7)
Geometric parameters (Å, º) top
O1—C11.3306 (18)C01A—H01B0.9600
O1—C02A1.408 (14)C01A—H01C0.9600
O1—C02B1.516 (14)C01B—H01D0.9600
O2—C11.1884 (19)C01B—H01E0.9600
O3—C71.3541 (18)C01B—H01F0.9600
O3—C81.4304 (17)C3—C41.379 (2)
C1—C21.487 (2)C3—H3A0.9300
C02A—C01A1.39 (2)C4—C51.372 (3)
C02A—H02A0.9700C4—H4A0.9300
C02A—H02B0.9700C5—C61.376 (2)
C02B—C01B1.455 (15)C5—H5A0.9300
C02B—H02C0.9700C6—C71.394 (2)
C02B—H02D0.9700C6—H6A0.9300
C2—C31.386 (2)C8—C8i1.479 (3)
C2—C71.402 (2)C8—H8A0.9700
C01A—H01A0.9600C8—H8B0.9700
C1—O1—C02A122.1 (7)C02B—C01B—H01F109.5
C1—O1—C02B112.8 (5)H01D—C01B—H01F109.5
C02A—O1—C02B12.6 (12)H01E—C01B—H01F109.5
C7—O3—C8117.59 (11)C4—C3—C2121.27 (16)
O2—C1—O1123.04 (15)C4—C3—H3A119.4
O2—C1—C2125.41 (14)C2—C3—H3A119.4
O1—C1—C2111.49 (13)C5—C4—C3119.41 (16)
C01A—C02A—O1107.4 (10)C5—C4—H4A120.3
C01A—C02A—H02A110.2C3—C4—H4A120.3
O1—C02A—H02A110.2C4—C5—C6121.09 (16)
C01A—C02A—H02B110.2C4—C5—H5A119.5
O1—C02A—H02B110.2C6—C5—H5A119.5
H02A—C02A—H02B108.5C5—C6—C7119.74 (15)
C01B—C02B—O1108.4 (10)C5—C6—H6A120.1
C01B—C02B—H02C110.0C7—C6—H6A120.1
O1—C02B—H02C110.0O3—C7—C6123.51 (13)
C01B—C02B—H02D110.0O3—C7—C2116.73 (12)
O1—C02B—H02D110.0C6—C7—C2119.73 (14)
H02C—C02B—H02D108.4O3—C8—C8i108.37 (12)
C3—C2—C7118.74 (14)O3—C8—H8A110.0
C3—C2—C1119.91 (13)C8i—C8—H8A110.0
C7—C2—C1121.32 (13)O3—C8—H8B110.0
C02B—C01B—H01D109.5C8i—C8—H8B110.0
C02B—C01B—H01E109.5H8A—C8—H8B108.4
H01D—C01B—H01E109.5
C02A—O1—C1—O24.9 (7)C1—C2—C3—C4177.81 (15)
C02B—O1—C1—O2−4.7 (6)C2—C3—C4—C51.1 (3)
C02A—O1—C1—C2−172.4 (7)C3—C4—C5—C6−0.8 (3)
C02B—O1—C1—C2177.9 (6)C4—C5—C6—C7−0.1 (3)
C1—O1—C02A—C01A−107.6 (14)C8—O3—C7—C6−1.2 (2)
C02B—O1—C02A—C01A−63 (4)C8—O3—C7—C2176.78 (13)
C1—O1—C02B—C01B−156.1 (10)C5—C6—C7—O3178.61 (15)
C02A—O1—C02B—C01B64 (4)C5—C6—C7—C20.7 (2)
O2—C1—C2—C3−136.02 (18)C3—C2—C7—O3−178.45 (13)
O1—C1—C2—C341.24 (19)C1—C2—C7—O33.3 (2)
O2—C1—C2—C742.3 (2)C3—C2—C7—C6−0.4 (2)
O1—C1—C2—C7−140.48 (14)C1—C2—C7—C6−178.72 (13)
C7—C2—C3—C4−0.5 (2)C7—O3—C8—C8i179.76 (14)
Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formulaC20H22O6
Mr358.38
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)298
a, b, c (Å)21.805 (4), 9.871 (2), 8.8646 (18)
V (Å3)1908.0 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.35 × 0.31 × 0.28
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.858, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		11280, 2192, 1543
Rint0.023
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.132, 1.04
No. of reflections2192
No. of parameters140
No. of restraints24
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.17, −0.14

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors are grateful for financial support from the National Fundation of China (21261002).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationBruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.  Google Scholar
 First citationChanthapally, A., Kole, G. K., Qian, K., Tan, G. K., Gao, S. & Vittal, J. J. (2012). Chem. Eur. J. 8, 7869–7877.  Web of Science CSD CrossRef Google Scholar
 First citationChen, X. & Liu, G. (2002). Chem. Eur. J. 8, 4811–4817.  CrossRef PubMed CAS Google Scholar
 First citationHou, L.-M. & Kan, Y.-H. (2007). Acta Cryst. E63, o2157–o2158.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMa, Z., Liang, B. & Lu, W. (2012). Acta Cryst. E68, m370.  CSD CrossRef IUCr Journals Google Scholar
 First citationMa, Z. & Liu, S.-X. (2002). Chin. J. Struct. Chem. 21, 533–537.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYan, C., Li, K., Wei, S.-C., Wang, H.-P., Fu, L., Pan, M. & Su, C.-Y. (2012). J. Mater. Chem. 22, 9846–9852.  Web of Science CSD CrossRef 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 70| Part 5| May 2014| Page o552
doi:10.1107/S1600536814007673
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