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 12| December 2010| Page o3078
https://doi.org/10.1107/S1600536810044193

2,4-Di­chloro-N-(1,3-thia­zol-2-yl)benzamide

Sohail Saeed,a* Naghmana Rashida and Wing-Tak Wongb

aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, Pakistan, and bDepartment of Chemistry, University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong SAR, People's Republic of China
*Correspondence e-mail: Sohail262001@yahoo.com

(Received 5 October 2010; accepted 28 October 2010; online 6 November 2010)

In the mol­ecular structure of the title compound, C10H6Cl2N2OS, the dihedral angle between the benzene plane and the plane defined by the amide functionality is 8.6 (1)°, while the thia­zole ring plane is twisted with respect to the amide plane by 68.71 (5)°. In the crystal, pairs of inter­molecular N—H⋯N hydrogen-bond inter­actions connect the mol­ecules into inversion dimers. π–π inter­actions are also observed between neighbouring thia­zole and phen­yl rings [centroid–centroid distance = 3.5905 (13) Å] and a weak C—H⋯π interaction also occurs.

Related literature

For the synthesis of related thia­zole derivatives and their application, see: Raman et al. (2000[Raman, P., Razavi, H. & Kelly, J. W. (2000). Org. Lett. 2, 3289-3292.]); Yunus et al. (2007[Yunus, U., Tahir, M. K., Bhatti, M. H., Ali, S. & Helliwell, M. (2007). Acta Cryst. E63, o3690.], 2008[Yunus, U., Tahir, M. K., Bhatti, M. H. & Wong, W.-Y. (2008). Acta Cryst. E64, o722.]). For microwave-assisted synthesis of amides, see Wang et al. (2008[Wang, X.-J., Yang, Q., Liu, F. & You, Q.-D. (2008). Synth. Commun. 38, 1028-1035.]).

[Scheme 1]

Experimental

Crystal data

  • C10H6Cl2N2OS

  • Mr = 273.13

  • Monoclinic, P 21 /c

  • a = 14.054 (3) Å

  • b = 13.063 (3) Å

  • c = 6.2880 (14) Å

  • β = 101.578 (3)°

  • V = 1130.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.74 mm−1

  • T = 304 K

  • 0.38 × 0.27 × 0.07 mm
Data collection

  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.768, Tmax = 0.950

  • 5906 measured reflections

  • 1993 independent reflections

  • 1820 reflections with I > 2σ(I)

  • Rint = 0.014
Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.080

  • S = 1.06

  • 1993 reflections

  • 149 parameters

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

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thia­zole ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2N⋯N1i 0.79 (2) 2.09 (2) 2.880 (2) 178 (2)
C1—H1⋯Cg1ii 0.93 2.81 3.501 (2) 132
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and CrystalStructure (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELX97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810044193/im2236sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044193/im2236Isup2.hkl

checkCIF report


Comment top

Substituted and unsubstituted thiazole derivatives are of great importance in biological systems due to their vast range of biological activities such as anti-inflammatory, analgestic and antipyretic (Raman et al., 2000; Yunus et al., 2007, 2008). On the other hand, amide compounds have extensive applications in pharmaceutical industry (Wang et al., 2008).

The title compound, 2,4-dichloro-N-thiazol-2-yl-benzamide, C10H6Cl2N2OS, crystallizes in the monoclinic space group P21/c (#14). The molecule is not planar showing a dihedral angle of 8.6 (1)° of the amide group, C3—C5/N2/O1 with respect to the phenyl ring plane, C5—C10/Cl1/Cl2. The thiazolyl ring, C1—C3/N1/S1, is twisted (68.71 (5)°) relative to the amide group. In additon, the phenyl ring plane makes a dihedral angle of 74.89 (5)° with the thiazole ring plane.

There are pair-wise inter-molecular N2—H2N···N1 H-bond interactions linking the molecules into dimeric arrangements. There are also π–π interactions between neighbouring thiazole, S1/N1/C1—C3 (Cg1), and phenyl rings, C5—C10 (Cg2), in the crystal lattice. The distance between ring centroids Cg1 and Cg2 is 3.5905 Å, and dihedral angle between them is determined to 0°.

There is no residual solvent accessible void volume in the unit cell.

Related literature top

For the synthesis of related thiazole derivatives and their application, see: Raman et al. (2000); Yunus et al. (2007, 2008). For microwave-assisted synthesis of amides, see Wang et al. (2008).

Experimental top

A mixture of 2,4-dichlorobenzoyl chloride (0.01 mol) and 2-aminothiazole (0.01 mol) was refluxed in acetone (50 ml) for 1.5 h. After cooling to room temperature, the mixture was poured into acidified cold water. The resulting solid was filtered and washed with cold acetone (yield: 72%). Single crystals of the title compound suitable for single-crystal X-ray analysis were obtained by recrystallization of the light yellow solid from ethyl acetate.

Refinement top

The structure was solved by direct methods (SHELXS97) and expanded using Fourier techniques. All non-H atoms were refined anisotropically. C-bound H atoms are all placed geometrically C—H = 0.93 Å for phenyl H-atoms. They were refined using a riding model with Uiso(H) = 1.2 Ueq (Carrier). N-bound H atoms were located from difference Fourier map and are refined isotropically.

Highest peak is 0.25 at (0.9753, 0.3236, 0.26385) [0.97Å from Cl2] Deepest hole is -0.24 at (0.2315, 0.6265, 0.1208) [0.79Å from Cl1]

Structure description top

Substituted and unsubstituted thiazole derivatives are of great importance in biological systems due to their vast range of biological activities such as anti-inflammatory, analgestic and antipyretic (Raman et al., 2000; Yunus et al., 2007, 2008). On the other hand, amide compounds have extensive applications in pharmaceutical industry (Wang et al., 2008).

The title compound, 2,4-dichloro-N-thiazol-2-yl-benzamide, C10H6Cl2N2OS, crystallizes in the monoclinic space group P21/c (#14). The molecule is not planar showing a dihedral angle of 8.6 (1)° of the amide group, C3—C5/N2/O1 with respect to the phenyl ring plane, C5—C10/Cl1/Cl2. The thiazolyl ring, C1—C3/N1/S1, is twisted (68.71 (5)°) relative to the amide group. In additon, the phenyl ring plane makes a dihedral angle of 74.89 (5)° with the thiazole ring plane.

There are pair-wise inter-molecular N2—H2N···N1 H-bond interactions linking the molecules into dimeric arrangements. There are also π–π interactions between neighbouring thiazole, S1/N1/C1—C3 (Cg1), and phenyl rings, C5—C10 (Cg2), in the crystal lattice. The distance between ring centroids Cg1 and Cg2 is 3.5905 Å, and dihedral angle between them is determined to 0°.

There is no residual solvent accessible void volume in the unit cell.

For the synthesis of related thiazole derivatives and their application, see: Raman et al. (2000); Yunus et al. (2007, 2008). For microwave-assisted synthesis of amides, see Wang et al. (2008).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006) and CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELX97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP plot of the compound with thermal ellipsoids at the 50% probability level and showing the atom numbering scheme.
[Figure 2] Fig. 2. Packing diagram.
2,4-Dichloro-N-(1,3-thiazol-2-yl)benzamide top
Crystal data top
C10H6Cl2N2OSF(000) = 552
Mr = 273.13Dx = 1.604 Mg m−3
Monoclinic, P21/cMelting point: 487 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.054 (3) ÅCell parameters from 6065 reflections
b = 13.063 (3) Åθ = 2.2–25.0°
c = 6.2880 (14) ŵ = 0.74 mm−1
β = 101.578 (3)°T = 304 K
V = 1130.8 (4) Å3Block, colourless
Z = 40.38 × 0.27 × 0.07 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer		1993 independent reflections
Radiation source: fine-focus sealed tube1820 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→15
Tmin = 0.768, Tmax = 0.950k = −15→13
5906 measured reflectionsl = −6→7
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0375P)2 + 0.4293P]
where P = (Fo2 + 2Fc2)/3
1993 reflections(Δ/σ)max < 0.001
149 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C10H6Cl2N2OSV = 1130.8 (4) Å3
Mr = 273.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.054 (3) ŵ = 0.74 mm−1
b = 13.063 (3) ÅT = 304 K
c = 6.2880 (14) Å0.38 × 0.27 × 0.07 mm
β = 101.578 (3)°
Data collection top
Bruker SMART 1000 CCD
diffractometer		1993 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1820 reflections with I > 2σ(I)
Tmin = 0.768, Tmax = 0.950Rint = 0.014
5906 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.25 e Å−3
1993 reflectionsΔρmin = −0.24 e Å−3
149 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
Cl10.24941 (4)0.64173 (4)0.24448 (11)0.0739 (2)
Cl20.02120 (5)0.61769 (6)0.82771 (11)0.0849 (2)
S10.41434 (3)0.32850 (4)0.00755 (7)0.04892 (15)
O10.25039 (10)0.34891 (11)0.1798 (2)0.0592 (4)
N10.53725 (10)0.42950 (11)0.2878 (2)0.0452 (3)
N20.38052 (10)0.43647 (12)0.3593 (3)0.0441 (3)
C10.53294 (15)0.33469 (15)−0.0224 (3)0.0536 (5)
H10.55680.3037−0.13430.064*
C20.58651 (14)0.39011 (15)0.1371 (3)0.0500 (4)
H20.65250.40130.14570.060*
C30.44612 (12)0.40332 (12)0.2379 (3)0.0399 (4)
C40.28500 (12)0.41126 (13)0.3182 (3)0.0436 (4)
C50.22451 (12)0.46497 (13)0.4549 (3)0.0435 (4)
C60.20114 (12)0.56805 (14)0.4270 (3)0.0471 (4)
C70.13838 (13)0.61528 (15)0.5405 (3)0.0549 (5)
H70.12200.68390.51750.066*
C80.10102 (13)0.55811 (18)0.6880 (3)0.0571 (5)
C90.12440 (15)0.45612 (18)0.7240 (4)0.0637 (5)
H90.09970.41910.82710.076*
C100.18494 (14)0.40987 (16)0.6047 (3)0.0561 (5)
H100.19940.34070.62520.067*
H2N0.4017 (14)0.4739 (16)0.456 (3)0.048 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0751 (4)0.0560 (3)0.1005 (5)0.0071 (3)0.0411 (3)0.0226 (3)
Cl20.0658 (4)0.1064 (5)0.0910 (5)0.0030 (3)0.0361 (3)−0.0242 (4)
S10.0525 (3)0.0473 (3)0.0460 (3)−0.00460 (19)0.0078 (2)−0.01145 (19)
O10.0506 (8)0.0593 (8)0.0655 (9)−0.0091 (6)0.0061 (6)−0.0187 (7)
N10.0420 (8)0.0449 (8)0.0487 (8)−0.0020 (6)0.0095 (6)−0.0084 (6)
N20.0398 (8)0.0430 (8)0.0485 (8)−0.0022 (6)0.0064 (6)−0.0130 (7)
C10.0596 (11)0.0544 (11)0.0499 (10)−0.0013 (9)0.0186 (9)−0.0099 (8)
C20.0471 (10)0.0517 (11)0.0540 (10)−0.0015 (8)0.0168 (8)−0.0067 (8)
C30.0446 (9)0.0331 (8)0.0411 (9)0.0008 (7)0.0065 (7)−0.0029 (7)
C40.0424 (9)0.0385 (9)0.0479 (9)−0.0003 (7)0.0042 (7)−0.0012 (7)
C50.0344 (8)0.0457 (9)0.0482 (9)−0.0023 (7)0.0035 (7)−0.0020 (7)
C60.0399 (9)0.0460 (10)0.0555 (10)−0.0028 (7)0.0098 (8)−0.0009 (8)
C70.0451 (10)0.0489 (11)0.0705 (13)0.0011 (8)0.0108 (9)−0.0080 (9)
C80.0402 (9)0.0740 (14)0.0580 (11)−0.0009 (9)0.0123 (8)−0.0108 (10)
C90.0597 (12)0.0747 (15)0.0614 (12)−0.0019 (11)0.0234 (10)0.0083 (11)
C100.0534 (11)0.0518 (11)0.0635 (12)0.0001 (9)0.0123 (9)0.0086 (9)
Geometric parameters (Å, º) top
Cl1—C61.7370 (19)C2—H20.9300
Cl2—C81.741 (2)C4—C51.499 (2)
S1—C11.716 (2)C5—C101.387 (3)
S1—C31.7299 (16)C5—C61.389 (3)
O1—C41.219 (2)C6—C71.386 (3)
N1—C31.302 (2)C7—C81.374 (3)
N1—C21.381 (2)C7—H70.9300
N2—C41.356 (2)C8—C91.380 (3)
N2—C31.379 (2)C9—C101.381 (3)
N2—H2N0.79 (2)C9—H90.9300
C1—C21.339 (3)C10—H100.9300
C1—H10.9300
C1—S1—C388.40 (9)C10—C5—C4119.82 (16)
C3—N1—C2109.94 (15)C6—C5—C4121.89 (16)
C4—N2—C3124.36 (15)C7—C6—C5121.70 (17)
C4—N2—H2N120.1 (14)C7—C6—Cl1117.84 (15)
C3—N2—H2N115.5 (14)C5—C6—Cl1120.46 (14)
C2—C1—S1110.84 (14)C8—C7—C6118.32 (19)
C2—C1—H1124.6C8—C7—H7120.8
S1—C1—H1124.6C6—C7—H7120.8
C1—C2—N1115.56 (17)C7—C8—C9121.65 (19)
C1—C2—H2122.2C7—C8—Cl2118.02 (17)
N1—C2—H2122.2C9—C8—Cl2120.32 (17)
N1—C3—N2121.23 (15)C8—C9—C10119.04 (19)
N1—C3—S1115.25 (13)C8—C9—H9120.5
N2—C3—S1123.49 (13)C10—C9—H9120.5
O1—C4—N2122.43 (17)C9—C10—C5121.08 (19)
O1—C4—C5122.07 (15)C9—C10—H10119.5
N2—C4—C5115.51 (15)C5—C10—H10119.5
C10—C5—C6118.16 (17)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the thiazole ring.
D—H···AD—HH···AD···AD—H···A
N2—H2N···N1i0.79 (2)2.09 (2)2.880 (2)178 (2)
C1—H1···Cg1ii0.932.813.501 (2)132
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC10H6Cl2N2OS
Mr273.13
Crystal system, space groupMonoclinic, P21/c
Temperature (K)304
a, b, c (Å)14.054 (3), 13.063 (3), 6.2880 (14)
β (°) 101.578 (3)
V (Å3)1130.8 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.74
Crystal size (mm)0.38 × 0.27 × 0.07
Data collection
DiffractometerBruker SMART 1000 CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.768, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections		5906, 1993, 1820
Rint0.014
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.080, 1.06
No. of reflections1993
No. of parameters149
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.24

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2006) and CrystalStructure (Rigaku/MSC, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008), SHELX97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the thiazole ring.
D—H···AD—HH···AD···AD—H···A
N2—H2N···N1i0.79 (2)2.09 (2)2.880 (2)178 (2)
C1—H1···Cg1ii0.932.813.501 (2)132
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2.
 

Acknowledgements

The authors are grateful to the Department of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad and the University of Hong Kong, Pokfulam, Hong Kong SAR, People's Republic of China for providing the laboratory and analytical facilities.

References

First citationBruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2006). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationJohnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationRaman, P., Razavi, H. & Kelly, J. W. (2000). Org. Lett. 2, 3289–3292.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationRigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, X.-J., Yang, Q., Liu, F. & You, Q.-D. (2008). Synth. Commun. 38, 1028–1035.  Web of Science CrossRef CAS Google Scholar
 First citationYunus, U., Tahir, M. K., Bhatti, M. H., Ali, S. & Helliwell, M. (2007). Acta Cryst. E63, o3690.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationYunus, U., Tahir, M. K., Bhatti, M. H. & Wong, W.-Y. (2008). Acta Cryst. E64, o722.  Web of Science CSD CrossRef 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 12| December 2010| Page o3078
https://doi.org/10.1107/S1600536810044193
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