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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages o1750-o1751

N-(4-Acetyl­phen­yl)-4-meth­­oxy­benzene­sulfonamide

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: suchada.c@psu.ac.th

(Received 21 October 2013; accepted 31 October 2013; online 6 November 2013)

The title compound, C15H15NO4S, was obtained by the condensation of 4-amino­aceto­phenone and 4-meth­oxy­benzene­sulfonyl chloride. The dihedral angle between the benzene rings is 86.56 (9)° and the mol­ecule has an approximate V-shaped conformation. The C atom of the meth­oxy group is roughly coplanar with its attached ring [deviation = 0.177 (3) Å], as is the methyl C atom of the acetyl group with its ring [deviation = 0.065 (2) Å]. An intra­molecular C—H⋯O inter­action generates an S(6) ring. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into [010] chains. Weak C—H⋯π inter­actions are also observed.

Related literature

For related structures, see: Li et al. (2006[Li, X.-M., Zeng, C.-C., Xu, Y.-S., Yan, H., Zheng, D.-W. & Zhong, R. G. (2006). J. Chem. Crystallogr. 36, 357-363.]); Xu et al. (2005[Xu, Y.-S., Zeng, C.-C., Li, X.-M. & Zhong, R.-G. (2005). Acta Cryst. E61, o3802-o3804.]). For background to and applications of sulfonamides, see: Alsughayer et al. (2011[Alsughayer, A., Elassar, A.-Z. A., Mustafa, S. & Sagheer, F. A. (2011). J. Biomater. Nanobiotechnol. 2, 144-149.]); Dragostin et al. (2013[Dragostin, O. M., Lupascu, F., Vasile, C., Mares, M., Nastasa, V., Moraru, R. F., Pieptu, D. & Profire, L. (2013). Molecules, 18, 4140-4157.]);

[Scheme 1]

Experimental

Crystal data
  • C15H15NO4S

  • Mr = 305.35

  • Monoclinic, P 21 /c

  • a = 12.8220 (3) Å

  • b = 8.2709 (2) Å

  • c = 14.6165 (4) Å

  • β = 112.841 (1)°

  • V = 1428.52 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 298 K

  • 0.48 × 0.44 × 0.33 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.894, Tmax = 0.924

  • 15571 measured reflections

  • 4120 independent reflections

  • 2593 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.135

  • S = 1.04

  • 4120 reflections

  • 196 parameters

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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N1⋯O3i 0.85 (2) 2.05 (2) 2.896 (2) 172.3 (19)
C8—H8A⋯O2 0.93 2.38 3.030 (2) 127
C9—H9A⋯O1ii 0.93 2.53 3.459 (2) 174
C14—H14ACg1i 0.96 2.83 3.630 (3) 141
C14—H14CCg2iii 0.96 2.83 3.529 (2) 130
C15—H15CCg1iv 0.96 2.99 3.804 (3) 144
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+2; (iv) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Sulfonamides containing an –SO2NH– group can be found in many pharmacologically active compounds: recent reports have described antibacterial (Alsughayer et al., 2011) and antioxidant (Dragostin et al., 2013) behaviour. As part of our ongoing research in this field, the title compound (I), a 4-methoxybenzene-sulfonamide derivative, was synthesized for being used as starting material for various syntheses. Herein the crystal structure of (I) is reported.

Figure 1 shows the molecular structure of (I), C15H15NO4S, suggesting a V-shaped conformation (Fig. 2). The benzene rings make the dihedral angle of 86.56 (9)°. The methoxy group is almost co-planar with its attached benzene ring with the deviation of 0.0310 (2) Å for the eight non H atoms (C1–C6/O4/C15) and the torsion angle C15–O4–C4–C5 = -2.2 (3)°. The amide group and acetyl substituent also lie in almost the same plane with the bound benzene ring with the deviation of 0.0220 (2) Å for the ten non H atoms (C7–C14/N1/O3) and the torsion angles of C11–C10–C13–O3 = -177.28 (18)° and C11–C10–C13–C14 = 2.6 (3)°. The dihedral angle between these two planes [C1–C6/O4/C15 and C7–C14/N1/O3] is 88.38 (7)° (Fig. 2). An intramolecular C8—H8A···O2 weak interaction generates an S(6) ring (Fig. 1) Bond distances of (I) are comparable with those in related structures (Li et al., 2006 and Xu et al., 2005).

In the crystal (Fig. 3), the molecules are linked by N—H···O hydrogen bonds and C—H···O weak interactions (Table 1) into chains along [010]. Weak C—H···π interactions are also observed (Table 1).

Related literature top

For related structures, see: Li et al. (2006); Xu et al. (2005). For background to and applications of sulfonamides, see: Alsughayer et al. (2011); Dragostin et al. (2013);

Experimental top

The title compound was synthesized by condensation of 4-aminoacetophenone (0.40 g, 3 mmol) and 4-methoxybenzenesulfonyl chloride in CH2Cl2 (30 ml) in the presence of pyridine. The reaction mixture was refluxed for 24 hr at 40 °C and monitored with TLC for the completion of the reaction. Water was then added and the concoction was extracted with CH2Cl2. The solvent was evaporated under reduced pressure to yield the resulting solid of the title compound (yield 68%). Yellow blocks of (I) were recrystalized from acetone:CH3OH solution (1:1 v/v) by slow evaporation of the solvent at room temperature after several days, Mp. 448–449 K.

Refinement top

Amide H atoms was located from the difference maps and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C—H) = 0.93 Å for aromatic and 0.96 for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids. The intramolecular C—H···O hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. The V-shape conformation of the molecule.
[Figure 3] Fig. 3. The crystal packing of the title compound viewed along the c axis. Hydrogen bonds were shown as dashed lines.
N-(4-Acetylphenyl)-4-methoxybenzenesulfonamide top
Crystal data top
C15H15NO4SF(000) = 640
Mr = 305.35Dx = 1.420 Mg m3
Monoclinic, P21/cMelting point = 448–449 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.8220 (3) ÅCell parameters from 4120 reflections
b = 8.2709 (2) Åθ = 1.7–29.9°
c = 14.6165 (4) ŵ = 0.24 mm1
β = 112.841 (1)°T = 298 K
V = 1428.52 (6) Å3Block, yellow
Z = 40.48 × 0.44 × 0.33 mm
Data collection top
Bruker APEXII CCD
diffractometer
4120 independent reflections
Radiation source: sealed tube2593 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ϕ and ω scansθmax = 29.9°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1717
Tmin = 0.894, Tmax = 0.924k = 1111
15571 measured reflectionsl = 2019
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0625P)2 + 0.0913P]
where P = (Fo2 + 2Fc2)/3
4120 reflections(Δ/σ)max = 0.001
196 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C15H15NO4SV = 1428.52 (6) Å3
Mr = 305.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.8220 (3) ŵ = 0.24 mm1
b = 8.2709 (2) ÅT = 298 K
c = 14.6165 (4) Å0.48 × 0.44 × 0.33 mm
β = 112.841 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
4120 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2593 reflections with I > 2σ(I)
Tmin = 0.894, Tmax = 0.924Rint = 0.043
15571 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.20 e Å3
4120 reflectionsΔρmin = 0.34 e Å3
196 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
S10.21179 (4)1.00630 (5)1.08283 (4)0.04186 (15)
O10.21200 (12)1.17413 (16)1.10664 (11)0.0546 (4)
O20.14687 (11)0.89569 (17)1.11408 (11)0.0529 (4)
O30.48523 (14)0.21499 (16)1.11408 (12)0.0624 (4)
O40.05688 (12)0.98389 (16)0.64850 (11)0.0540 (4)
N10.34483 (13)0.95337 (19)1.13298 (12)0.0408 (4)
C10.16988 (14)0.9867 (2)0.95362 (14)0.0378 (4)
C20.22355 (15)1.0787 (2)0.90451 (14)0.0418 (4)
H2A0.28491.14390.94040.050*
C30.18492 (15)1.0722 (2)0.80272 (15)0.0432 (4)
H3A0.22091.13210.76970.052*
C40.09193 (16)0.9760 (2)0.74878 (14)0.0415 (4)
C50.04067 (17)0.8825 (2)0.79829 (15)0.0487 (5)
H5A0.02010.81610.76270.058*
C60.07979 (16)0.8882 (2)0.90017 (15)0.0466 (5)
H6A0.04540.82540.93330.056*
C70.38891 (14)0.7983 (2)1.12776 (12)0.0353 (4)
C80.32855 (16)0.6554 (2)1.12191 (14)0.0422 (4)
H8A0.25490.65911.11910.051*
C90.37892 (16)0.5091 (2)1.12029 (15)0.0427 (4)
H9A0.33810.41441.11570.051*
C100.48954 (16)0.4993 (2)1.12535 (13)0.0381 (4)
C110.54871 (16)0.6432 (2)1.13233 (14)0.0422 (4)
H11A0.62300.63941.13680.051*
C120.49943 (15)0.7902 (2)1.13275 (14)0.0413 (4)
H12A0.54000.88491.13640.050*
C130.54079 (17)0.3380 (2)1.12393 (14)0.0427 (4)
C140.66124 (18)0.3279 (3)1.13447 (15)0.0542 (5)
H14A0.68140.21681.13160.081*
H14B0.70940.37361.19700.081*
H14C0.67040.38701.08150.081*
C150.0427 (2)0.8943 (3)0.59083 (17)0.0666 (6)
H15A0.06020.91170.52150.100*
H15B0.10500.93000.60670.100*
H15C0.02970.78120.60570.100*
H1N10.3889 (18)1.031 (2)1.1334 (15)0.047 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0414 (2)0.0396 (3)0.0475 (3)0.00720 (19)0.0204 (2)0.00056 (19)
O10.0597 (9)0.0422 (8)0.0628 (9)0.0125 (6)0.0248 (7)0.0084 (6)
O20.0485 (8)0.0588 (9)0.0603 (9)0.0041 (6)0.0309 (7)0.0070 (7)
O30.0769 (10)0.0329 (7)0.0842 (11)0.0013 (7)0.0386 (9)0.0008 (7)
O40.0561 (9)0.0552 (9)0.0464 (9)0.0140 (7)0.0152 (7)0.0038 (6)
N10.0411 (8)0.0332 (8)0.0468 (10)0.0015 (7)0.0156 (7)0.0022 (7)
C10.0337 (8)0.0337 (9)0.0464 (10)0.0046 (7)0.0158 (8)0.0028 (7)
C20.0365 (9)0.0369 (10)0.0508 (12)0.0058 (7)0.0156 (8)0.0021 (8)
C30.0404 (10)0.0378 (10)0.0528 (12)0.0039 (8)0.0196 (9)0.0016 (8)
C40.0412 (9)0.0374 (10)0.0438 (11)0.0011 (8)0.0143 (8)0.0015 (8)
C50.0444 (10)0.0437 (11)0.0526 (12)0.0126 (8)0.0130 (9)0.0018 (9)
C60.0435 (10)0.0425 (10)0.0552 (12)0.0073 (8)0.0209 (9)0.0039 (9)
C70.0381 (8)0.0344 (9)0.0321 (9)0.0022 (7)0.0121 (7)0.0007 (7)
C80.0385 (9)0.0405 (10)0.0496 (11)0.0001 (8)0.0193 (8)0.0004 (8)
C90.0455 (10)0.0337 (9)0.0513 (11)0.0035 (8)0.0213 (9)0.0010 (8)
C100.0440 (9)0.0346 (9)0.0356 (9)0.0016 (7)0.0153 (8)0.0026 (7)
C110.0373 (9)0.0411 (10)0.0494 (11)0.0022 (8)0.0179 (8)0.0020 (8)
C120.0391 (9)0.0346 (9)0.0506 (11)0.0030 (7)0.0180 (8)0.0004 (8)
C130.0552 (11)0.0377 (10)0.0356 (10)0.0069 (8)0.0180 (9)0.0038 (7)
C140.0590 (12)0.0497 (12)0.0530 (13)0.0166 (10)0.0208 (10)0.0003 (9)
C150.0587 (14)0.0790 (16)0.0519 (14)0.0175 (12)0.0103 (11)0.0074 (12)
Geometric parameters (Å, º) top
S1—O21.4261 (14)C7—C121.392 (2)
S1—O11.4308 (13)C7—C81.397 (2)
S1—N11.6335 (16)C8—C91.376 (2)
S1—C11.7590 (19)C8—H8A0.9300
O3—C131.218 (2)C9—C101.394 (3)
O4—C41.358 (2)C9—H9A0.9300
O4—C151.433 (3)C10—C111.394 (2)
N1—C71.416 (2)C10—C131.491 (2)
N1—H1N10.85 (2)C11—C121.371 (2)
C1—C61.381 (3)C11—H11A0.9300
C1—C21.397 (3)C12—H12A0.9300
C2—C31.375 (3)C13—C141.494 (3)
C2—H2A0.9300C14—H14A0.9600
C3—C41.395 (3)C14—H14B0.9600
C3—H3A0.9300C14—H14C0.9600
C4—C51.387 (3)C15—H15A0.9600
C5—C61.375 (3)C15—H15B0.9600
C5—H5A0.9300C15—H15C0.9600
C6—H6A0.9300
O2—S1—O1119.39 (9)C9—C8—C7119.50 (17)
O2—S1—N1108.79 (8)C9—C8—H8A120.3
O1—S1—N1104.35 (9)C7—C8—H8A120.3
O2—S1—C1108.17 (9)C8—C9—C10121.67 (17)
O1—S1—C1108.75 (8)C8—C9—H9A119.2
N1—S1—C1106.72 (8)C10—C9—H9A119.2
C4—O4—C15117.12 (16)C11—C10—C9117.90 (16)
C7—N1—S1126.00 (13)C11—C10—C13122.34 (17)
C7—N1—H1N1113.8 (14)C9—C10—C13119.76 (16)
S1—N1—H1N1112.0 (14)C12—C11—C10121.26 (17)
C6—C1—C2120.09 (18)C12—C11—H11A119.4
C6—C1—S1120.10 (15)C10—C11—H11A119.4
C2—C1—S1119.69 (14)C11—C12—C7120.25 (16)
C3—C2—C1119.49 (17)C11—C12—H12A119.9
C3—C2—H2A120.3C7—C12—H12A119.9
C1—C2—H2A120.3O3—C13—C10120.55 (18)
C2—C3—C4120.26 (18)O3—C13—C14119.98 (17)
C2—C3—H3A119.9C10—C13—C14119.47 (17)
C4—C3—H3A119.9C13—C14—H14A109.5
O4—C4—C5124.41 (17)C13—C14—H14B109.5
O4—C4—C3115.76 (17)H14A—C14—H14B109.5
C5—C4—C3119.82 (18)C13—C14—H14C109.5
C6—C5—C4119.90 (18)H14A—C14—H14C109.5
C6—C5—H5A120.0H14B—C14—H14C109.5
C4—C5—H5A120.0O4—C15—H15A109.5
C5—C6—C1120.40 (18)O4—C15—H15B109.5
C5—C6—H6A119.8H15A—C15—H15B109.5
C1—C6—H6A119.8O4—C15—H15C109.5
C12—C7—C8119.41 (16)H15A—C15—H15C109.5
C12—C7—N1117.40 (16)H15B—C15—H15C109.5
C8—C7—N1123.14 (17)
O2—S1—N1—C753.22 (18)C2—C1—C6—C51.4 (3)
O1—S1—N1—C7178.31 (15)S1—C1—C6—C5174.65 (15)
C1—S1—N1—C763.27 (17)S1—N1—C7—C12151.37 (15)
O2—S1—C1—C65.98 (17)S1—N1—C7—C831.2 (3)
O1—S1—C1—C6125.08 (15)C12—C7—C8—C90.6 (3)
N1—S1—C1—C6122.88 (15)N1—C7—C8—C9177.92 (17)
O2—S1—C1—C2177.94 (13)C7—C8—C9—C100.6 (3)
O1—S1—C1—C251.00 (16)C8—C9—C10—C110.1 (3)
N1—S1—C1—C261.03 (15)C8—C9—C10—C13179.65 (17)
C6—C1—C2—C31.0 (3)C9—C10—C11—C121.0 (3)
S1—C1—C2—C3175.13 (14)C13—C10—C11—C12179.50 (17)
C1—C2—C3—C40.8 (3)C10—C11—C12—C71.0 (3)
C15—O4—C4—C52.7 (3)C8—C7—C12—C110.3 (3)
C15—O4—C4—C3176.22 (18)N1—C7—C12—C11177.24 (17)
C2—C3—C4—O4176.85 (16)C11—C10—C13—O3177.28 (18)
C2—C3—C4—C52.2 (3)C9—C10—C13—O33.2 (3)
O4—C4—C5—C6177.21 (18)C11—C10—C13—C142.6 (3)
C3—C4—C5—C61.7 (3)C9—C10—C13—C14176.96 (18)
C4—C5—C6—C10.1 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O3i0.85 (2)2.05 (2)2.896 (2)172.3 (19)
C8—H8A···O20.932.383.030 (2)127
C9—H9A···O1ii0.932.533.459 (2)174
C14—H14A···Cg1i0.962.833.630 (3)141
C14—H14C···Cg2iii0.962.833.529 (2)130
C15—H15C···Cg1iv0.962.993.804 (3)144
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y+1, z+2; (iv) x, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O3i0.85 (2)2.05 (2)2.896 (2)172.3 (19)
C8—H8A···O20.932.383.030 (2)127
C9—H9A···O1ii0.932.533.459 (2)174
C14—H14A···Cg1i0.962.833.630 (3)141
C14—H14C···Cg2iii0.962.833.529 (2)130
C15—H15C···Cg1iv0.962.993.804 (3)144
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y+1, z+2; (iv) x, y1/2, z+3/2.
 

Footnotes

Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0137/2554) is gratefully acknowledged. CSCK thanks the Universiti Sains Malaysia for a postdoctoral research fellowship. The authors extend their appreciation to Prince of Songkla University and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

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Volume 69| Part 12| December 2013| Pages o1750-o1751
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