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ISSN: 2414-3146

(3aR,6R)-3,3,6-Tri­methyl-3,3a,4,5,6,7-hexa­hydro-2H-indazole-2-carbo­thio­amide

aLaboratoire de Synthèse Organique et Physico-Chimie Moléculaire, Département de Chimie, Faculté, des Sciences, Semlalia BP 2390, Marrakech 40001, Morocco, bInstitut de Chimie Moléculaire de Reims, CNRS UMR 7312 Bât. Europol'Agro, Moulin de la Housse UFR Sciences, BP 1039–51687 Reims Cédex 2, France, and cLaboratoire de Chimie des Substances Naturelles, "Unité Associé au CNRST (URAC16)", Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco
*Correspondence e-mail: berraho@uca.ac.ma

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 16 March 2016; accepted 6 April 2016; online 12 April 2016)

The title compound, C11H19N3S, was prepared by the reaction of (R)-pulegone with thio­semicarbazide in acidic medium, using ethanol as solvent. The mol­ecule is built up from fused six and five-membered rings. The six-membered ring adopts a chair conformation, while the five-membered ring displays an envelope conformation with the dimethyl-substituted C atom as the flap. The dihedral angle between the mean planes of the two rings is 20.35 (6)°. In the crystal, mol­ecules are linked by N—H⋯N and N—H⋯S hydrogen bonds into chains running parallel to [100].

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

In recent years, the synthesis of heterocyclic systems containing nitro­gen has attracted great inter­est because of their broad spectrum of pharmacological activities. In particular, indazole is a crucial heterocyclic skeleton present in a wide variety of drugs, many natural products and biologically active compounds (Gautam et al., 2015[Gautam, D. & Chaudhary, R. P. (2015). Spectrochim. Acta Part A, 135, 219-226.]). Compounds containing the indazole skeleton are known to display a broad spectrum of potent pharmacological activities including anti-inflammatory (Rosati et al., 2007[Rosati, O., Curini, M., Marcotullio, M. C., Macchiarulo, A., Perfumi, M., Mattioli, L., Rismondo, F. & Cravotto, G. (2007). Bioorg. Med. Chem. 15, 3463-3473.]), anti-depressant (Bailey et al., 1985[Bailey, D. M., Hansen, P. E., Hlavac, A. G., Baizman, E. R., Pearl, J., DeFelice, A. F. & Feigenson, M. E. (1985). J. Med. Chem. 28, 256-260.]), anti­cancer (De Lena et al., 2001[De Lena, M., Lorusso, V., Latorre, A., Fanizza, G., Gargano, G., Caporusso, L., Guida, M., Catino, A., Crucitta, E., Sambiasi, D. & Mazzei, A. (2001). Eur. J. Cancer, 37, 364-368.]), anti­tuberculosis (Guo et al., 2010[Guo, S., Song, Y., Huang, Q., Yuan, H., Wan, B., Wang, Y., He, R., Beconi, M. G., Franzblau, S. G. & Kozikowski, A. P. (2010). J. Med. Chem. 53, 649-659.]) and anti­microbial activities (Ali et al., 2012[Ali, N., ali, S., Zakir, S., Patel, M. & Farooqui, M. (2012). Eur. J. Med. Chem. 50, 39-43.]). The therapeutic usefulness of these heterocyclic systems prompted us to prepare a new substituted 2H-indazole from a naturally occurring monoterpene. The title compound (3aR,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexa­hydro-2H-indazole-2-carbo­thio­amide was prepared by the reaction of (R)-pulegone with thio­semicarbazide in acidic medium, using ethanol as solvent. The resulting product obtained as diastereomeric mixture, was then crystallized from ethanol to give the new compound as white monocrystals.

The title mol­ecule, Fig. 1[link], contains a fused ring system and a carbo­thio­amide group as a substituent to the pyrazolidine ring. The six-membered ring (C1/C7/C8/C19—C12) has a chair conformation as indicated by puckering parameters QT = 0.5218 (16) Å, θ = 16.11 (18) and φ2 = 199.40 (16)°. The pyrazolidine ring (N1/N2/C1/C7/C14) adopts an envelope conformation with atom C14 as the flap; deviating by 0.341 (1) Å from the mean plane through the other four atoms in the ring.

[Figure 1]
Figure 1
Mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Labels very small

In the crystal, mol­ecules are linked by N—H⋯N and N—H⋯S hydrogen bonds into chains running parallel to [100] (Table 1[link] and Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3B⋯N1i 0.86 2.37 3.230 (3) 176
N3—H3A⋯S1ii 0.86 2.70 3.442 (3) 146
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].
[Figure 2]
Figure 2
Partial crystal packing view along the c axis of the title compound. The N—H⋯N and N—H⋯S hydrogen bonds (dashed lines; Table 1[link]) indicate the formation of a chain parallel to the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

Owing to the presence of the S atom, the absolute configuration could be fully confirmed, by refining the Flack parameter (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]), as C3a(R) and C6(R).

Synthesis and crystallization

A hot ethano­lic solution containing equimolar qu­anti­ties of thio­semicarbazide and (R)-pulegone with a few drops of concentrated HCl was heated under reflux. The progress of the reaction was monitored by TLC. After the completion of the reaction, the solvent was evaporated under reduced pressure and the crude product was purified by chromatography on silica gel (230–400 mesh) using hexa­ne/ethyl acetate (95:5) as eluent. The pure indazolic product was obtained in 64% yield as a diastereomeric mixture. Slow evaporation from an ethano­lic solution of the title compound gave crystals of the title compound, suitable for X-ray crystallographic analysis.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C11H19N3S
Mr 225.35
Crystal system, space group Orthorhombic, P212121
Temperature (K) 100
a, b, c (Å) 7.957 (5), 10.796 (5), 13.673 (5)
V3) 1174.6 (10)
Z 4
Radiation type Cu Kα
μ (mm−1) 2.21
Crystal size (mm) 0.24 × 0.2 × 0.15
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.618, 0.718
No. of measured, independent and observed [I > 2σ(I)] reflections 17550, 2315, 2270
Rint 0.027
(sin θ/λ)max−1) 0.618
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.054, 1.06
No. of reflections 2315
No. of parameters 140
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.22, −0.17
Absolute structure Parsons et al. (2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]), 972 Friedel pairs
Absolute structure parameter 0.028 (12)
Computer programs: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data


Experimental top

A hot ethanolic solution containing equimolar quantities of thiosemicarbazide and (R)-pulegone with a few drops of concentrated HCl was heated under reflux. The progress of the reaction was monitored by TLC. After the completion of the reaction, the solvent was evaporated under reduced pressure and the crude product was purified by chromatography on silica gel (230–400 mesh) using hexane/ethyl acetate (95:5) as eluent. The pure indazolic product was obtained in 64% yield as a diastereomeric mixture. Slow evaporation from an ethanolic solution of the title compound gave crystals of the title compound, suitable for X-ray crystallographic analysis.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description top

In recent years, the synthesis of heterocyclic systems containing nitrogen has attracted great interest because of their broad spectrum of pharmacological activities. In particular, indazole is a crucial heterocyclic skeleton present in a wide variety of drugs, many natural products and biologically active compounds (Gautam et al., 2015). Compounds containing the indazole skeleton are known to display a broad spectrum of potent pharmacological activities including anti-inflammatory (Rosati et al., 2007), anti-depressant (Bailey et al., 1985), anticancer (De Lena et al., 2001), antituberculosis (Guo et al., 2010) and antimicrobial activities (Ali et al., 2012). The therapeutic usefulness of these heterocyclic systems prompted us to prepare a new substituted 2H-indazole from a naturally occurring monoterpene. The title compound (3aR,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide was prepared by the reaction of (R)-pulegone with thiosemicarbazide in acidic medium, using ethanol as solvent. The resulting product obtained as diastereomeric mixture, was then crystallized from ethanol to give the new compound as white monocrystals. The structure of this new product was confirmed by its single-crystal X-ray structure.

The title molecule, Fig. 1, contains a fused ring system and a carbothioamide group as a substituent to the pyrazolidine ring. The six-membered ring (C1/C7/C8/C19—C12) has a chair conformation as indicated by puckering parameters QT = 0.5218 (16) Å, θ = 16.11 (18) and φ2 = 199.40 (16)°. The pyrazolidine ring (N1/N2/C1/C7/C14) adopts an envelope conformation with atom C14 as the flap; deviating by 0.341 (1) Å from the mean plane through the other four atoms in the ring.

In the crystal, molecules are linked by N—H···N and N—H···S hydrogen bonds into chains running parallel to [100] (Table 1 and Fig. 2).

Owing to the presence of the S atom, the absolute configuration could be fully confirmed, by refining the Flack parameter (Parsons et al., 2013), as C3a(R) and C6(R).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Partial crystal packing view along the c axis of the title compound. The N—H···N and N—H···S hydrogen bonds (dashed lines; Table 1) indicate the formation of a chain parallel to the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.
(3aR,6R)-3,3,6-Trimethyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide top
Crystal data top
C11H19N3SDx = 1.274 Mg m3
Mr = 225.35Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P212121Cell parameters from 17550 reflections
a = 7.957 (5) Åθ = 5.2–72.9°
b = 10.796 (5) ŵ = 2.21 mm1
c = 13.673 (5) ÅT = 100 K
V = 1174.6 (10) Å3Prismatic, colourless
Z = 40.24 × 0.2 × 0.15 mm
F(000) = 488
Data collection top
Bruker APEXII CCD
diffractometer
2315 independent reflections
Radiation source: microsource2270 reflections with I > 2σ(I)
Multi-layer mirror monochromatorRint = 0.027
φ and ω scansθmax = 72.2°, θmin = 5.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 99
Tmin = 0.618, Tmax = 0.718k = 1213
17550 measured reflectionsl = 1616
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)] = 0.021H-atom parameters constrained
wR(F2) = 0.054 w = 1/[σ2(Fo2) + (0.0309P)2 + 0.2126P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2315 reflectionsΔρmax = 0.22 e Å3
140 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Parsons et al. (2013), 972 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.028 (12)
Crystal data top
C11H19N3SV = 1174.6 (10) Å3
Mr = 225.35Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.957 (5) ŵ = 2.21 mm1
b = 10.796 (5) ÅT = 100 K
c = 13.673 (5) Å0.24 × 0.2 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
2315 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2270 reflections with I > 2σ(I)
Tmin = 0.618, Tmax = 0.718Rint = 0.027
17550 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.054Δρmax = 0.22 e Å3
S = 1.06Δρmin = 0.17 e Å3
2315 reflectionsAbsolute structure: Parsons et al. (2013), 972 Friedel pairs
140 parametersAbsolute structure parameter: 0.028 (12)
0 restraints
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S10.15695 (3)0.04077 (2)0.529496 (19)0.01460 (8)
C10.68856 (13)0.02162 (11)0.35481 (8)0.0111 (2)
N20.45543 (12)0.03660 (9)0.43699 (7)0.01126 (18)
N10.59405 (12)0.10135 (9)0.39659 (7)0.01179 (19)
C40.33782 (15)0.10291 (10)0.48530 (7)0.0117 (2)
N30.37036 (13)0.22324 (9)0.49959 (7)0.0167 (2)
H3A0.46260.25480.47840.020*
H3B0.29900.26900.53000.020*
C60.31991 (15)0.10083 (12)0.31667 (9)0.0171 (2)
H6A0.21000.08150.34130.026*
H6B0.31940.18270.28930.026*
H6C0.35030.04210.26700.026*
C70.63141 (14)0.10999 (10)0.36496 (8)0.0117 (2)
H70.69470.14620.41940.014*
C80.66596 (16)0.19039 (10)0.27468 (9)0.0168 (2)
H8A0.58510.17130.22380.020*
H8B0.65420.27720.29160.020*
C90.40770 (15)0.18861 (10)0.48000 (9)0.0167 (2)
H9A0.46610.16620.53880.025*
H9B0.44320.26950.45930.025*
H9C0.28890.18940.49220.025*
C100.87482 (14)0.02785 (11)0.21395 (8)0.0148 (2)
H100.99090.01840.19120.018*
C110.85262 (14)0.05119 (10)0.30711 (8)0.0137 (2)
H11A0.94390.03440.35230.016*
H11B0.85610.13840.29020.016*
C120.84475 (17)0.16553 (11)0.23718 (9)0.0176 (2)
H12A0.86400.21410.17860.021*
H12B0.92500.19220.28620.021*
C130.75792 (16)0.01904 (12)0.13366 (9)0.0191 (3)
H13A0.76740.03360.07730.029*
H13B0.78870.10210.11620.029*
H13C0.64410.01810.15690.029*
C140.44718 (14)0.09470 (10)0.40007 (8)0.0116 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01105 (13)0.01600 (13)0.01675 (13)0.00067 (11)0.00364 (10)0.00051 (11)
C10.0114 (5)0.0133 (5)0.0086 (5)0.0002 (4)0.0023 (4)0.0002 (4)
N20.0104 (4)0.0093 (4)0.0141 (4)0.0019 (4)0.0017 (3)0.0004 (4)
N10.0098 (4)0.0138 (4)0.0118 (4)0.0025 (4)0.0008 (3)0.0007 (4)
C40.0118 (5)0.0136 (5)0.0098 (5)0.0015 (4)0.0011 (4)0.0013 (4)
N30.0140 (5)0.0134 (5)0.0228 (5)0.0001 (4)0.0053 (4)0.0047 (4)
C60.0134 (6)0.0202 (6)0.0178 (5)0.0002 (5)0.0018 (5)0.0035 (5)
C70.0105 (5)0.0121 (5)0.0125 (5)0.0008 (4)0.0001 (4)0.0012 (4)
C80.0183 (6)0.0123 (5)0.0197 (5)0.0000 (5)0.0035 (5)0.0034 (4)
C90.0172 (5)0.0128 (5)0.0200 (6)0.0022 (4)0.0020 (5)0.0034 (5)
C100.0108 (5)0.0195 (6)0.0141 (5)0.0014 (5)0.0029 (4)0.0009 (5)
C110.0100 (5)0.0164 (5)0.0148 (5)0.0015 (5)0.0007 (4)0.0004 (4)
C120.0163 (6)0.0175 (5)0.0189 (5)0.0045 (5)0.0032 (5)0.0029 (4)
C130.0182 (6)0.0260 (7)0.0131 (5)0.0003 (5)0.0011 (4)0.0014 (5)
C140.0120 (5)0.0093 (5)0.0134 (5)0.0002 (4)0.0002 (4)0.0010 (4)
Geometric parameters (Å, º) top
S1—C41.6990 (14)C8—H8A0.9700
C1—N11.2778 (16)C8—H8B0.9700
C1—C111.4938 (16)C9—C141.5235 (16)
C1—C71.4983 (16)C9—H9A0.9600
N2—C41.3507 (15)C9—H9B0.9600
N2—N11.4180 (14)C9—H9C0.9600
N2—C141.5062 (15)C10—C131.5254 (16)
C4—N31.3390 (15)C10—C121.5387 (18)
N3—H3A0.8600C10—C111.5433 (15)
N3—H3B0.8600C10—H100.9800
C6—C141.5265 (17)C11—H11A0.9700
C6—H6A0.9600C11—H11B0.9700
C6—H6B0.9600C12—H12A0.9700
C6—H6C0.9600C12—H12B0.9700
C7—C81.5339 (15)C13—H13A0.9600
C7—C141.5513 (17)C13—H13B0.9600
C7—H70.9800C13—H13C0.9600
C8—C121.5358 (19)
N1—C1—C11124.44 (11)C14—C9—H9C109.5
N1—C1—C7114.76 (10)H9A—C9—H9C109.5
C11—C1—C7120.55 (10)H9B—C9—H9C109.5
C4—N2—N1117.92 (10)C13—C10—C12111.98 (10)
C4—N2—C14129.24 (9)C13—C10—C11109.92 (10)
N1—N2—C14111.55 (8)C12—C10—C11110.24 (9)
C1—N1—N2107.45 (10)C13—C10—H10108.2
N3—C4—N2116.85 (10)C12—C10—H10108.2
N3—C4—S1119.67 (9)C11—C10—H10108.2
N2—C4—S1123.47 (9)C1—C11—C10110.02 (9)
C4—N3—H3A120.0C1—C11—H11A109.7
C4—N3—H3B120.0C10—C11—H11A109.7
H3A—N3—H3B120.0C1—C11—H11B109.7
C14—C6—H6A109.5C10—C11—H11B109.7
C14—C6—H6B109.5H11A—C11—H11B108.2
H6A—C6—H6B109.5C8—C12—C10112.45 (10)
C14—C6—H6C109.5C8—C12—H12A109.1
H6A—C6—H6C109.5C10—C12—H12A109.1
H6B—C6—H6C109.5C8—C12—H12B109.1
C1—C7—C8114.07 (9)C10—C12—H12B109.1
C1—C7—C14102.39 (9)H12A—C12—H12B107.8
C8—C7—C14118.59 (10)C10—C13—H13A109.5
C1—C7—H7107.0C10—C13—H13B109.5
C8—C7—H7107.0H13A—C13—H13B109.5
C14—C7—H7107.0C10—C13—H13C109.5
C7—C8—C12109.62 (10)H13A—C13—H13C109.5
C7—C8—H8A109.7H13B—C13—H13C109.5
C12—C8—H8A109.7N2—C14—C9113.26 (9)
C7—C8—H8B109.7N2—C14—C6108.67 (9)
C12—C8—H8B109.7C9—C14—C6111.73 (10)
H8A—C8—H8B108.2N2—C14—C799.36 (8)
C14—C9—H9A109.5C9—C14—C7110.25 (9)
C14—C9—H9B109.5C6—C14—C7113.02 (10)
H9A—C9—H9B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···N1i0.862.373.230 (3)176
N3—H3A···S1ii0.862.703.442 (3)146
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···N1i0.862.373.230 (3)176
N3—H3A···S1ii0.862.703.442 (3)146
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC11H19N3S
Mr225.35
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)7.957 (5), 10.796 (5), 13.673 (5)
V3)1174.6 (10)
Z4
Radiation typeCu Kα
µ (mm1)2.21
Crystal size (mm)0.24 × 0.2 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.618, 0.718
No. of measured, independent and
observed [I > 2σ(I)] reflections
17550, 2315, 2270
Rint0.027
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.054, 1.06
No. of reflections2315
No. of parameters140
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.17
Absolute structureParsons et al. (2013), 972 Friedel pairs
Absolute structure parameter0.028 (12)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

 

Acknowledgements

The authors thank Pr. Auhmani Abdelouhed as laboratory manager.

References

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