Crystal structure of (1S,3R,8R,9S,10R)-10-bromo­methyl-2,2-di­chloro-9,10-ep­oxy-3,7,7-tri­methyl­tri­cyclo­[6.4.0.01,3]dodeca­ne

Benharref, A.; El Ammari, L.; Saadi, M.; Berraho, M.

doi:10.1107/S205698901500657X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages o284-o285

https://doi.org/10.1107/S205698901500657X

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Crystal structure of (1S,3R,8R,9S,10R)-10-bromomethyl-2,2-dichloro-9,10-epoxy-3,7,7-trimethyltricyclo[6.4.0.0^1,3]dodecane

Ahmed Benharref,^a Lahcen El Ammari,^b Mohamed Saadi ^b and Moha Berraho ^a ^*

^aLaboratoire de Chimie des Substances Naturelles, Unité Associé au CNRST (URAC16), Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: berraho@uca.ma

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 27 March 2015; accepted 31 March 2015; online 9 April 2015)

The title compound, C₁₆H₂₃BrCl₂O, was synthesized in three steps from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (cedrus atlantica). The molecule is built up from two fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a screw-boat conformation, whereas the seven-membered ring displays a twist-boat conformation. The absolute structure was established unambiguously from anomalous dispersion effects.

Keywords: crystal structure; β-himachalene derivative; π–π interactions.

CCDC reference: 1057239

1. Related literature

For background to β-himachalene, see: El Haib et al. (2011 ). For the reactivity of this sesquiterpene and its derivatives, see: El Jamili et al. (2002 ); Benharref et al. (2013 ); Zaki et al. (2014 ). For the synthesis of the title compound, see: Bimoussa et al. (2013 ). For their potential antifungal activity against the phytopathogen Botrytis cinerea, see: Daoubi et al. (2004 ).

2. Experimental

2.1. Crystal data

C₁₆H₂₃BrCl₂O
M_r = 382.15
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.8748 (5) Å
b = 11.2102 (6) Å
c = 16.8597 (8) Å
V = 1677.34 (15) Å³
Z = 4
Mo Kα radiation
μ = 2.76 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.16 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.648, T_max = 0.746
23384 measured reflections
3419 independent reflections
3135 reflections with I > 2σ(I)
R_int = 0.034

2.3. Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.04
3419 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.53 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ), 1450 Friedel pairs
Absolute structure parameter: 0.012 (9)

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1057239

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S205698901500657X/rz5154sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901500657X/rz5154Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901500657X/rz5154Isup3.cml

checkCIF report

Comment top

This work is a part of our ongoing program concerning the valorization of the most abundant essential oils in Morocco, such as cedrus atlantica. This oil is made up mainly (75%) of bicyclic sesquiterpene hydrocarbons, among which is found the compound β-himachalene (El Haib et al., 2011). The reactivity of this sesquiterpene and its derivatives has been studied extensively by our team in order to prepare new products having biological properties (El jamili et al., 2002; Benharref et al., 2013, Zaki et al.,2014). Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against phytopathogen Botrytis cinerea (Daoubi et al., 2004). In this work we present the crystal structure of the title compound.

The molecule contains fused six- and seven-membered rings, each linked to a three-membered ring as shown in Fig. 1. The six-membered ring has a screw boat conformation, as indicated by the total puckering amplitude Q_T = 0.476 (3) Å and spherical polar angle θ = 129.5 (4)° with φ = 263.4 (5)°, whereas the seven-membered ring displays a twist boat conformation with Q_T = 1.1465 (34) Å,θ = 88.54 (18)°, φ2 = -152.04 (18)° and φ3 = 72.86 (6)°. The dihedral angle between the mean planes trough the six- and seven-membered rings is 57.7 (2)°. The three-membered rings (C2/C3/O4) and (C6–C8) are nearly perpendicular to the six-membered ring (C1–C6) with a dihedral angles of 79.8 (3)° and 84.7 (3)°, respectively. Owing to the presence of Cl and Br atoms, the absolute configuration could be fully confirmed, by refining the Flack parameter (Flack & Bernardinelli, 2000) as S, R, R, S and R for C atoms at positions 1, 3, 8, 9 and 10, respectively.

Related literature top

For background to β-himachalene, see: El Haib et al. (2011). For the reactivity of this sesquiterpene and its derivatives, see: El jamili et al. (2002); Benharref et al. (2013); Zaki et al. (2014). For the synthesis of the title compound, see: Bimoussa et al. (2013). For their potential antifungal activity against the phytopathogen Botrytis cinerea, see: Daoubi et al. (2004).

Experimental top

A stoichiometric quantity of m-chloroperbenzoic acid (m-CPBA) was added to a 100 ml flask containing a solution of (1S,3R,8R)-10-bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.0¹,³]dodec-9-ene (Bimoussa et al., 2013) (750 mg, 2 mmol) in CH₂Cl₂ (40 ml). The reaction mixture was stirred at ambient temperature for 2 h, then treated with a 10% solution of sodium hydrogencarbonate. The aqueous phase was extracted with ether and the organic phases were dried and concentrated. Chromatography of the residue on silica (hexane/ethyl acetate, 98:2 v/v) allowed the isolation of the title compound with a yield of 90% (700 mg, 1.8 mmol). The product was recrystallized from cyclohexane.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

(1S,3R,8R,9S,10R)-10-Bromomethyl-2,2-dichloro-9,10-epoxy-3,7,7-trimethyltricyclo[6.4.0.0^1,3]dodecane top

Crystal data top

C₁₆H₂₃BrCl₂O	F(000) = 784
M_r = 382.15	D_x = 1.513 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3419 reflections
a = 8.8748 (5) Å	θ = 2.2–26.4°
b = 11.2102 (6) Å	µ = 2.76 mm⁻¹
c = 16.8597 (8) Å	T = 296 K
V = 1677.34 (15) Å³	Prism, colourless
Z = 4	0.35 × 0.25 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	3419 independent reflections
Radiation source: fine-focus sealed tube	3135 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and φ scans	θ_max = 26.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
T_min = 0.648, T_max = 0.746	k = −14→14
23384 measured reflections	l = −21→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.035P)² + 1.0813P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3419 reflections	Δρ_max = 0.65 e Å⁻³
184 parameters	Δρ_min = −0.53 e Å⁻³
0 restraints	Absolute structure: Flack & Bernardinelli (2000), 1450 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (9)

Crystal data top

C₁₆H₂₃BrCl₂O	V = 1677.34 (15) Å³
M_r = 382.15	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.8748 (5) Å	µ = 2.76 mm⁻¹
b = 11.2102 (6) Å	T = 296 K
c = 16.8597 (8) Å	0.35 × 0.25 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	3419 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3135 reflections with I > 2σ(I)
T_min = 0.648, T_max = 0.746	R_int = 0.034
23384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.65 e Å⁻³
S = 1.04	Δρ_min = −0.53 e Å⁻³
3419 reflections	Absolute structure: Flack & Bernardinelli (2000), 1450 Friedel pairs
184 parameters	Absolute structure parameter: 0.012 (9)
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

	x	y	z	U_iso*/U_eq
C1	0.8156 (3)	0.2763 (2)	0.75464 (16)	0.0311 (5)
H1	0.8658	0.3365	0.7875	0.037*
C2	0.7910 (3)	0.3332 (2)	0.67448 (17)	0.0349 (6)
H2	0.8806	0.3401	0.6408	0.042*
C3	0.6468 (3)	0.3276 (2)	0.63277 (17)	0.0382 (6)
C4	0.5134 (3)	0.2638 (3)	0.66859 (18)	0.0439 (7)
H4A	0.4679	0.2133	0.6285	0.053*
H4B	0.4389	0.3224	0.6845	0.053*
C5	0.5541 (3)	0.1874 (3)	0.74026 (17)	0.0362 (6)
H5A	0.4632	0.1688	0.7697	0.043*
H5B	0.5976	0.1128	0.7221	0.043*
C6	0.6652 (3)	0.2497 (2)	0.79482 (15)	0.0286 (5)
C7	0.6026 (3)	0.3367 (2)	0.85487 (16)	0.0347 (6)
C8	0.6680 (4)	0.2217 (2)	0.88460 (16)	0.0398 (6)
C9	0.8207 (4)	0.2258 (3)	0.9237 (2)	0.0570 (9)
H9A	0.8075	0.2281	0.9808	0.068*
H9B	0.8719	0.2985	0.9079	0.068*
C10	0.9190 (5)	0.1185 (4)	0.9020 (3)	0.0755 (13)
H10A	1.0238	0.1393	0.9107	0.091*
H10B	0.8946	0.0530	0.9373	0.091*
C11	0.9007 (5)	0.0760 (3)	0.8162 (3)	0.0603 (10)
H11A	0.7992	0.0451	0.8104	0.072*
H11B	0.9693	0.0098	0.8081	0.072*
C12	0.9274 (3)	0.1671 (3)	0.7491 (2)	0.0457 (7)
C13	0.5657 (5)	0.1268 (3)	0.9185 (2)	0.0592 (9)
H13A	0.5498	0.1418	0.9739	0.089*
H13B	0.6116	0.0499	0.9118	0.089*
H13C	0.4707	0.1284	0.8913	0.089*
C14	1.0895 (4)	0.2161 (4)	0.7539 (3)	0.0668 (11)
H14A	1.1026	0.2583	0.8029	0.100*
H14B	1.1071	0.2694	0.7103	0.100*
H14C	1.1597	0.1511	0.7514	0.100*
C15	0.9119 (4)	0.0994 (3)	0.6701 (3)	0.0586 (10)
H15A	0.9802	0.0329	0.6697	0.088*
H15B	0.9354	0.1520	0.6270	0.088*
H15C	0.8105	0.0709	0.6645	0.088*
C16	0.6457 (5)	0.3478 (3)	0.54456 (19)	0.0554 (9)
H16A	0.7275	0.4010	0.5303	0.067*
H16B	0.5517	0.3854	0.5293	0.067*
Br1	0.66817 (6)	0.19765 (4)	0.48772 (2)	0.07821 (17)
O4	0.6911 (3)	0.43512 (16)	0.67456 (12)	0.0418 (5)
Cl1	0.40574 (9)	0.36000 (8)	0.85958 (5)	0.0521 (2)
Cl2	0.69214 (10)	0.47409 (6)	0.87514 (5)	0.04980 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0274 (12)	0.0251 (11)	0.0408 (14)	−0.0013 (10)	−0.0036 (11)	−0.0025 (10)
C2	0.0353 (13)	0.0311 (13)	0.0383 (14)	−0.0042 (10)	0.0061 (11)	−0.0017 (11)
C3	0.0477 (15)	0.0347 (14)	0.0323 (13)	0.0006 (11)	−0.0016 (12)	−0.0043 (11)
C4	0.0345 (14)	0.0591 (19)	0.0382 (15)	−0.0083 (13)	−0.0069 (12)	−0.0046 (13)
C5	0.0305 (13)	0.0362 (13)	0.0418 (15)	−0.0096 (11)	0.0009 (12)	−0.0039 (12)
C6	0.0271 (11)	0.0265 (11)	0.0323 (12)	−0.0027 (10)	−0.0045 (11)	0.0017 (9)
C7	0.0353 (13)	0.0355 (14)	0.0331 (14)	−0.0013 (11)	−0.0001 (11)	0.0001 (11)
C8	0.0485 (16)	0.0368 (14)	0.0341 (14)	−0.0056 (13)	−0.0056 (13)	0.0077 (11)
C9	0.064 (2)	0.061 (2)	0.0459 (18)	−0.0004 (18)	−0.0205 (18)	0.0138 (15)
C10	0.075 (3)	0.071 (3)	0.081 (3)	0.017 (2)	−0.029 (2)	0.027 (2)
C11	0.0554 (19)	0.0392 (16)	0.086 (3)	0.0153 (15)	−0.009 (2)	0.0085 (17)
C12	0.0330 (15)	0.0369 (15)	0.067 (2)	0.0061 (12)	−0.0024 (14)	−0.0027 (14)
C13	0.076 (3)	0.052 (2)	0.049 (2)	−0.0088 (18)	0.0071 (18)	0.0157 (16)
C14	0.0316 (16)	0.060 (2)	0.109 (3)	0.0024 (15)	−0.0107 (18)	−0.006 (2)
C15	0.0434 (17)	0.0463 (18)	0.086 (3)	0.0076 (14)	0.0107 (18)	−0.0195 (18)
C16	0.079 (2)	0.0550 (19)	0.0326 (15)	0.0012 (18)	−0.0015 (16)	−0.0008 (14)
Br1	0.0966 (3)	0.0883 (3)	0.0497 (2)	0.0133 (3)	−0.0049 (2)	−0.0260 (2)
O4	0.0549 (12)	0.0313 (9)	0.0394 (11)	0.0054 (9)	−0.0052 (10)	0.0000 (8)
Cl1	0.0415 (4)	0.0631 (5)	0.0516 (5)	0.0067 (4)	0.0126 (3)	0.0000 (4)
Cl2	0.0638 (5)	0.0353 (3)	0.0504 (4)	−0.0044 (3)	−0.0037 (4)	−0.0109 (3)

Geometric parameters (Å, º) top

C1—C2	1.510 (4)	C9—C10	1.531 (6)
C1—C6	1.527 (4)	C9—H9A	0.9700
C1—C12	1.579 (4)	C9—H9B	0.9700
C1—H1	0.9800	C10—C11	1.530 (6)
C2—O4	1.446 (3)	C10—H10A	0.9700
C2—C3	1.462 (4)	C10—H10B	0.9700
C2—H2	0.9800	C11—C12	1.543 (5)
C3—O4	1.451 (3)	C11—H11A	0.9700
C3—C16	1.504 (4)	C11—H11B	0.9700
C3—C4	1.509 (4)	C12—C15	1.538 (5)
C4—C5	1.524 (4)	C12—C14	1.542 (4)
C4—H4A	0.9700	C13—H13A	0.9600
C4—H4B	0.9700	C13—H13B	0.9600
C5—C6	1.519 (4)	C13—H13C	0.9600
C5—H5A	0.9700	C14—H14A	0.9600
C5—H5B	0.9700	C14—H14B	0.9600
C6—C7	1.512 (4)	C14—H14C	0.9600
C6—C8	1.546 (4)	C15—H15A	0.9600
C7—C8	1.500 (4)	C15—H15B	0.9600
C7—Cl2	1.766 (3)	C15—H15C	0.9600
C7—Cl1	1.769 (3)	C16—Br1	1.947 (3)
C8—C9	1.507 (5)	C16—H16A	0.9700
C8—C13	1.511 (4)	C16—H16B	0.9700

C2—C1—C6	110.7 (2)	C8—C9—H9A	109.1
C2—C1—C12	111.4 (2)	C10—C9—H9A	109.1
C6—C1—C12	115.1 (2)	C8—C9—H9B	109.1
C2—C1—H1	106.3	C10—C9—H9B	109.1
C6—C1—H1	106.3	H9A—C9—H9B	107.8
C12—C1—H1	106.3	C11—C10—C9	114.2 (3)
O4—C2—C3	59.83 (17)	C11—C10—H10A	108.7
O4—C2—C1	114.9 (2)	C9—C10—H10A	108.7
C3—C2—C1	122.6 (2)	C11—C10—H10B	108.7
O4—C2—H2	115.8	C9—C10—H10B	108.7
C3—C2—H2	115.8	H10A—C10—H10B	107.6
C1—C2—H2	115.8	C10—C11—C12	118.1 (3)
O4—C3—C2	59.54 (17)	C10—C11—H11A	107.8
O4—C3—C16	110.9 (2)	C12—C11—H11A	107.8
C2—C3—C16	118.3 (3)	C10—C11—H11B	107.8
O4—C3—C4	114.4 (2)	C12—C11—H11B	107.8
C2—C3—C4	121.0 (2)	H11A—C11—H11B	107.1
C16—C3—C4	117.5 (3)	C15—C12—C14	107.7 (3)
C3—C4—C5	113.4 (2)	C15—C12—C11	107.1 (3)
C3—C4—H4A	108.9	C14—C12—C11	109.9 (3)
C5—C4—H4A	108.9	C15—C12—C1	112.2 (3)
C3—C4—H4B	108.9	C14—C12—C1	107.9 (2)
C5—C4—H4B	108.9	C11—C12—C1	111.9 (3)
H4A—C4—H4B	107.7	C8—C13—H13A	109.5
C6—C5—C4	112.1 (2)	C8—C13—H13B	109.5
C6—C5—H5A	109.2	H13A—C13—H13B	109.5
C4—C5—H5A	109.2	C8—C13—H13C	109.5
C6—C5—H5B	109.2	H13A—C13—H13C	109.5
C4—C5—H5B	109.2	H13B—C13—H13C	109.5
H5A—C5—H5B	107.9	C12—C14—H14A	109.5
C7—C6—C5	117.7 (2)	C12—C14—H14B	109.5
C7—C6—C1	119.5 (2)	H14A—C14—H14B	109.5
C5—C6—C1	112.9 (2)	C12—C14—H14C	109.5
C7—C6—C8	58.76 (18)	H14A—C14—H14C	109.5
C5—C6—C8	120.7 (2)	H14B—C14—H14C	109.5
C1—C6—C8	117.4 (2)	C12—C15—H15A	109.5
C8—C7—C6	61.77 (18)	C12—C15—H15B	109.5
C8—C7—Cl2	120.7 (2)	H15A—C15—H15B	109.5
C6—C7—Cl2	121.82 (19)	C12—C15—H15C	109.5
C8—C7—Cl1	119.6 (2)	H15A—C15—H15C	109.5
C6—C7—Cl1	119.2 (2)	H15B—C15—H15C	109.5
Cl2—C7—Cl1	107.87 (15)	C3—C16—Br1	110.8 (2)
C7—C8—C9	117.9 (2)	C3—C16—H16A	109.5
C7—C8—C13	119.9 (3)	Br1—C16—H16A	109.5
C9—C8—C13	113.3 (3)	C3—C16—H16B	109.5
C7—C8—C6	59.47 (17)	Br1—C16—H16B	109.5
C9—C8—C6	115.9 (3)	H16A—C16—H16B	108.1
C13—C8—C6	120.2 (3)	C2—O4—C3	60.63 (18)
C8—C9—C10	112.6 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₂₃BrCl₂O
M_r	382.15
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.8748 (5), 11.2102 (6), 16.8597 (8)
V (Å³)	1677.34 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.76
Crystal size (mm)	0.35 × 0.25 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.648, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	23384, 3419, 3135
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.04
No. of reflections	3419
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.53
Absolute structure	Flack & Bernardinelli (2000), 1450 Friedel pairs
Absolute structure parameter	0.012 (9)

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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