1-n-Decyl-5-nitro-1H-benzimidazol-2(3H)-one

Ouzidan, Y.; Kandri Rodi, Y.; Ladeira, S.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811004399

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o613

doi:10.1107/S1600536811004399

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1-n-Decyl-5-nitro-1H-benzimidazol-2(3H)-one

Younes Ouzidan,^a Y. Kandri Rodi,^a Sonia Ladeira,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 January 2011; accepted 6 February 2011; online 12 February 2011)

The benzimidazolone part of the title molecule, C₁₇H₂₅N₃O₃, is almost planar (r.m.s. deviation = 0.016 Å) and its mean plane is aligned at 7.9 (4) ° with respect to the mean plane of the nitro substituent. In the crystal, two molecules are disposed about a center of inversion, generating a N—H⋯O hydrogen-bonded cyclic dimer with a R₂²(8) graph-set motif.

Related literature

For the crystal structure of 1-isopropenyl-1H-benzimidazol-2(3H)-one, see: Saber et al. (2010 ) and for 5-nitro-1-n-octyl-1H-benzimidazol-2(3H)-one, see: Ouzidan et al. (2011 ). For graph-set notation, see: Etter (1990 ).

Experimental

Crystal data

C₁₇H₂₅N₃O₃
M_r = 319.40
Triclinic, $[P \overline 1]$
a = 5.4933 (2) Å
b = 10.3063 (4) Å
c = 16.1655 (6) Å
α = 106.504 (2)°
β = 98.545 (2)°
γ = 96.809 (2)°
V = 855.21 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.32 × 0.06 × 0.04 mm

Data collection

Bruker APEXII diffractometer
10701 measured reflections
2971 independent reflections
1600 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.175
S = 0.89
2971 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	1.92	2.784 (3)	168
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004399/zs2093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004399/zs2093Isup2.hkl

checkCIF report

Comment top

Tetraalkylammonium halides are used as phase-transfer catalyst in the synthesis of alkyl-substituted benzimidazolones. A previous study reported the 1-isopropenyl derivative in which the amino –NH unit forms a hydrogen bond to the inversion-related molecule to generate a hydrogen-bonded dimer (Saber et al., 2010). The present compound (Scheme I) features a long n-octyl chain that adopts an extended zigzag conformation (Fig. 1). The benzimidazolone part of the C₁₇H₂₅N₃O₃ molecule is planar (r.m.s. deviation 0.016 Å) and its mean plane is aligned at 7.9 (4) ° with respect to the mean plane of the nitro substituent. Two molecules are disposed about a center of inversion to generate a hydrogen-bonded cyclic dimer (Table 1), whose hydrogen-bonding motif is described by the R²₂(8) graph set (Etter, 1990).

Related literature top

For the crystal structure of 1-isopropenyl-1H-benzimidazol-2(3H)-one, see: Saber et al. (2010) and for 5-nitro-1-n-octyl-1H-benzimidazol-2(3H)-one, see: Ouzidan et al. (2011). For graph-set notation, see: Etter (1990).

Experimental top

To 5-nitro-1H-benzoimidazol-2(3H)-one (0.2 g, 1.1 mmol), potassium carbonate (0.30 g, 2.2 mmol) and tetra-n-butylammonium bromide (0.07 g, 0.2 mmol) in DMF (15 ml) was added 1-bromo-n-decane (0.46 ml, 2.2 mmol). Stirring was continued at room temperature for 6 h. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. The compound was recrystallized from diethyl ether to give colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot drawn at the 50% probability level (Barbour, 2001), of two molecules of C₁₇H₂₅N₃O₃ disposed about a center of inversion.

1-n-decyl-5-nitro-1H-benzimidazol-2(3H)-one top

Crystal data top

C₁₇H₂₅N₃O₃	Z = 2
M_r = 319.40	F(000) = 344
Triclinic, P1	D_x = 1.240 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4933 (2) Å	Cell parameters from 1521 reflections
b = 10.3063 (4) Å	θ = 2.7–27.3°
c = 16.1655 (6) Å	µ = 0.09 mm⁻¹
α = 106.504 (2)°	T = 293 K
β = 98.545 (2)°	Prism, colorless
γ = 96.809 (2)°	0.32 × 0.06 × 0.04 mm
V = 855.21 (6) Å³

Data collection top

Bruker APEXII diffractometer	1600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 25.0°, θ_min = 3.9°
ϕ and ω scans	h = −6→6
10701 measured reflections	k = −10→12
2971 independent reflections	l = −19→19

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.1056P)²] where P = (F_o² + 2F_c²)/3
S = 0.89	(Δ/σ)_max = 0.001
2971 reflections	Δρ_max = 0.30 e Å⁻³
209 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (6)

Crystal data top

C₁₇H₂₅N₃O₃	γ = 96.809 (2)°
M_r = 319.40	V = 855.21 (6) Å³
Triclinic, P1	Z = 2
a = 5.4933 (2) Å	Mo Kα radiation
b = 10.3063 (4) Å	µ = 0.09 mm⁻¹
c = 16.1655 (6) Å	T = 293 K
α = 106.504 (2)°	0.32 × 0.06 × 0.04 mm
β = 98.545 (2)°

Data collection top

Bruker APEXII diffractometer	1600 reflections with I > 2σ(I)
10701 measured reflections	R_int = 0.068
2971 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 0.89	Δρ_max = 0.30 e Å⁻³
2971 reflections	Δρ_min = −0.31 e Å⁻³
209 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.6868 (3)	0.57512 (19)	0.61197 (12)	0.0413 (6)
O2	0.8896 (4)	−0.0690 (2)	0.29737 (16)	0.0579 (7)
O3	1.2510 (4)	−0.0845 (2)	0.36526 (16)	0.0680 (7)
N1	0.7157 (4)	0.3830 (2)	0.49844 (15)	0.0357 (6)
H1	0.5863	0.3832	0.4592	0.043*
N2	0.9999 (4)	0.4426 (2)	0.61946 (15)	0.0337 (6)
N3	1.0691 (5)	−0.0264 (2)	0.35868 (19)	0.0482 (7)
C1	0.7879 (5)	0.4765 (3)	0.57918 (19)	0.0354 (7)
C2	0.8734 (5)	0.2871 (3)	0.48616 (18)	0.0328 (7)
C3	0.8717 (5)	0.1718 (3)	0.41760 (19)	0.0371 (7)
H3	0.7483	0.1435	0.3671	0.044*
C4	1.0672 (5)	0.1002 (3)	0.4288 (2)	0.0380 (7)
C5	1.2516 (5)	0.1396 (3)	0.5022 (2)	0.0397 (8)
H5	1.3801	0.0890	0.5052	0.048*
C6	1.2493 (5)	0.2538 (3)	0.5717 (2)	0.0385 (7)
H6	1.3723	0.2805	0.6223	0.046*
C7	1.0566 (5)	0.3268 (3)	0.56298 (19)	0.0347 (7)
C8	1.1434 (5)	0.5230 (3)	0.70567 (18)	0.0399 (7)
H8A	1.0786	0.6078	0.7254	0.048*
H8B	1.3157	0.5469	0.7007	0.048*
C9	1.1361 (5)	0.4479 (3)	0.77434 (19)	0.0420 (7)
H9A	1.1954	0.3618	0.7530	0.050*
H9B	1.2519	0.5027	0.8276	0.050*
C10	0.8830 (5)	0.4174 (3)	0.7976 (2)	0.0457 (8)
H10A	0.7678	0.3575	0.7457	0.055*
H10B	0.8185	0.5023	0.8171	0.055*
C11	0.8982 (5)	0.3489 (3)	0.8699 (2)	0.0463 (8)
H11A	0.9593	0.2632	0.8491	0.056*
H11B	1.0202	0.4076	0.9204	0.056*
C12	0.6562 (6)	0.3190 (3)	0.8998 (2)	0.0516 (9)
H12A	0.5896	0.4036	0.9179	0.062*
H12B	0.5366	0.2556	0.8505	0.062*
C13	0.6824 (6)	0.2585 (3)	0.9749 (2)	0.0492 (8)
H13A	0.8060	0.3210	1.0234	0.059*
H13B	0.7457	0.1731	0.9561	0.059*
C14	0.4445 (6)	0.2305 (3)	1.0082 (2)	0.0535 (9)
H14A	0.3754	0.3146	1.0235	0.064*
H14B	0.3244	0.1634	0.9608	0.064*
C15	0.4751 (6)	0.1780 (3)	1.0874 (2)	0.0531 (9)
H15A	0.5400	0.0926	1.0717	0.064*
H15B	0.5981	0.2439	1.1344	0.064*
C16	0.2378 (7)	0.1537 (4)	1.1214 (2)	0.0692 (11)
H16A	0.1189	0.0825	1.0760	0.083*
H16B	0.1659	0.2371	1.1331	0.083*
C17	0.2764 (8)	0.1116 (4)	1.2043 (3)	0.0862 (13)
H17A	0.1189	0.0965	1.2220	0.129*
H17B	0.3888	0.1832	1.2503	0.129*
H17C	0.3460	0.0286	1.1932	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0513 (12)	0.0398 (11)	0.0402 (12)	0.0189 (10)	0.0180 (10)	0.0148 (10)
O2	0.0723 (16)	0.0459 (14)	0.0531 (16)	0.0082 (12)	0.0178 (14)	0.0095 (12)
O3	0.0794 (17)	0.0556 (14)	0.0770 (18)	0.0342 (13)	0.0326 (14)	0.0149 (13)
N1	0.0405 (13)	0.0385 (13)	0.0363 (15)	0.0144 (11)	0.0142 (11)	0.0176 (13)
N2	0.0368 (13)	0.0354 (13)	0.0344 (14)	0.0097 (10)	0.0119 (11)	0.0151 (12)
N3	0.0618 (18)	0.0381 (15)	0.056 (2)	0.0155 (14)	0.0303 (16)	0.0194 (14)
C1	0.0446 (17)	0.0345 (16)	0.0357 (18)	0.0080 (14)	0.0186 (14)	0.0179 (15)
C2	0.0383 (16)	0.0332 (16)	0.0355 (18)	0.0072 (13)	0.0170 (14)	0.0184 (14)
C3	0.0440 (17)	0.0374 (16)	0.0355 (18)	0.0054 (13)	0.0146 (14)	0.0172 (15)
C4	0.0491 (18)	0.0321 (16)	0.0444 (19)	0.0096 (14)	0.0273 (16)	0.0192 (15)
C5	0.0412 (17)	0.0383 (17)	0.051 (2)	0.0139 (14)	0.0212 (16)	0.0215 (16)
C6	0.0371 (16)	0.0431 (17)	0.0436 (19)	0.0086 (13)	0.0137 (14)	0.0226 (16)
C7	0.0415 (16)	0.0346 (16)	0.0376 (18)	0.0073 (13)	0.0212 (14)	0.0191 (14)
C8	0.0435 (16)	0.0414 (17)	0.0352 (18)	0.0068 (13)	0.0102 (14)	0.0114 (15)
C9	0.0466 (17)	0.0414 (17)	0.0382 (18)	0.0102 (14)	0.0075 (14)	0.0119 (14)
C10	0.0541 (19)	0.0456 (18)	0.044 (2)	0.0130 (15)	0.0156 (16)	0.0185 (16)
C11	0.0561 (19)	0.0483 (18)	0.0399 (19)	0.0123 (15)	0.0140 (15)	0.0183 (16)
C12	0.064 (2)	0.0493 (19)	0.050 (2)	0.0120 (16)	0.0166 (17)	0.0237 (17)
C13	0.059 (2)	0.0508 (19)	0.043 (2)	0.0115 (16)	0.0125 (16)	0.0199 (16)
C14	0.060 (2)	0.056 (2)	0.054 (2)	0.0110 (16)	0.0165 (17)	0.0275 (18)
C15	0.070 (2)	0.0456 (18)	0.046 (2)	0.0063 (16)	0.0131 (18)	0.0188 (17)
C16	0.086 (3)	0.071 (2)	0.068 (3)	0.017 (2)	0.036 (2)	0.037 (2)
C17	0.136 (4)	0.076 (3)	0.063 (3)	0.012 (3)	0.041 (3)	0.038 (2)

Geometric parameters (Å, º) top

O1—C1	1.240 (3)	C10—C11	1.525 (4)
O2—N3	1.228 (3)	C10—H10A	0.9700
O3—N3	1.231 (3)	C10—H10B	0.9700
N1—C1	1.353 (3)	C11—C12	1.508 (4)
N1—C2	1.382 (3)	C11—H11A	0.9700
N1—H1	0.8800	C11—H11B	0.9700
N2—C1	1.379 (3)	C12—C13	1.511 (4)
N2—C7	1.382 (3)	C12—H12A	0.9700
N2—C8	1.454 (4)	C12—H12B	0.9700
N3—C4	1.468 (4)	C13—C14	1.513 (4)
C2—C3	1.374 (4)	C13—H13A	0.9700
C2—C7	1.402 (4)	C13—H13B	0.9700
C3—C4	1.391 (4)	C14—C15	1.520 (4)
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.367 (4)	C14—H14B	0.9700
C5—C6	1.380 (4)	C15—C16	1.509 (4)
C5—H5	0.9300	C15—H15A	0.9700
C6—C7	1.382 (3)	C15—H15B	0.9700
C6—H6	0.9300	C16—C17	1.517 (5)
C8—C9	1.526 (4)	C16—H16A	0.9700
C8—H8A	0.9700	C16—H16B	0.9700
C8—H8B	0.9700	C17—H17A	0.9600
C9—C10	1.514 (4)	C17—H17B	0.9600
C9—H9A	0.9700	C17—H17C	0.9600
C9—H9B	0.9700

C1—N1—C2	110.5 (2)	C9—C10—H10B	109.3
C1—N1—H1	124.7	C11—C10—H10B	109.3
C2—N1—H1	124.7	H10A—C10—H10B	108.0
C1—N2—C7	109.0 (2)	C12—C11—C10	115.4 (2)
C1—N2—C8	124.0 (2)	C12—C11—H11A	108.4
C7—N2—C8	126.9 (2)	C10—C11—H11A	108.4
O2—N3—O3	123.7 (3)	C12—C11—H11B	108.4
O2—N3—C4	118.5 (2)	C10—C11—H11B	108.4
O3—N3—C4	117.8 (3)	H11A—C11—H11B	107.5
O1—C1—N1	127.5 (3)	C13—C12—C11	113.7 (2)
O1—C1—N2	125.5 (3)	C13—C12—H12A	108.8
N1—C1—N2	107.0 (2)	C11—C12—H12A	108.8
C3—C2—N1	132.1 (3)	C13—C12—H12B	108.8
C3—C2—C7	121.8 (2)	C11—C12—H12B	108.8
N1—C2—C7	106.1 (2)	H12A—C12—H12B	107.7
C2—C3—C4	115.5 (3)	C12—C13—C14	115.2 (2)
C2—C3—H3	122.3	C12—C13—H13A	108.5
C4—C3—H3	122.3	C14—C13—H13A	108.5
C5—C4—C3	123.6 (3)	C12—C13—H13B	108.5
C5—C4—N3	118.8 (3)	C14—C13—H13B	108.5
C3—C4—N3	117.6 (3)	H13A—C13—H13B	107.5
C4—C5—C6	120.7 (2)	C15—C14—C13	115.0 (3)
C4—C5—H5	119.6	C15—C14—H14A	108.5
C6—C5—H5	119.6	C13—C14—H14A	108.5
C7—C6—C5	117.2 (3)	C15—C14—H14B	108.5
C7—C6—H6	121.4	C13—C14—H14B	108.5
C5—C6—H6	121.4	H14A—C14—H14B	107.5
N2—C7—C6	131.5 (3)	C16—C15—C14	114.5 (3)
N2—C7—C2	107.3 (2)	C16—C15—H15A	108.6
C6—C7—C2	121.2 (3)	C14—C15—H15A	108.6
N2—C8—C9	113.2 (2)	C16—C15—H15B	108.6
N2—C8—H8A	108.9	C14—C15—H15B	108.6
C9—C8—H8A	108.9	H15A—C15—H15B	107.6
N2—C8—H8B	108.9	C15—C16—C17	113.5 (3)
C9—C8—H8B	108.9	C15—C16—H16A	108.9
H8A—C8—H8B	107.8	C17—C16—H16A	108.9
C10—C9—C8	115.7 (2)	C15—C16—H16B	108.9
C10—C9—H9A	108.4	C17—C16—H16B	108.9
C8—C9—H9A	108.4	H16A—C16—H16B	107.7
C10—C9—H9B	108.4	C16—C17—H17A	109.5
C8—C9—H9B	108.4	C16—C17—H17B	109.5
H9A—C9—H9B	107.4	H17A—C17—H17B	109.5
C9—C10—C11	111.6 (2)	C16—C17—H17C	109.5
C9—C10—H10A	109.3	H17A—C17—H17C	109.5
C11—C10—H10A	109.3	H17B—C17—H17C	109.5

C2—N1—C1—O1	−179.0 (2)	C8—N2—C7—C6	2.5 (4)
C2—N1—C1—N2	1.4 (3)	C1—N2—C7—C2	−0.7 (3)
C7—N2—C1—O1	180.0 (2)	C8—N2—C7—C2	−177.4 (2)
C8—N2—C1—O1	−3.2 (4)	C5—C6—C7—N2	179.3 (3)
C7—N2—C1—N1	−0.4 (3)	C5—C6—C7—C2	−0.8 (4)
C8—N2—C1—N1	176.4 (2)	C3—C2—C7—N2	−177.8 (2)
C1—N1—C2—C3	177.4 (3)	N1—C2—C7—N2	1.4 (3)
C1—N1—C2—C7	−1.7 (3)	C3—C2—C7—C6	2.3 (4)
N1—C2—C3—C4	179.3 (2)	N1—C2—C7—C6	−178.4 (2)
C7—C2—C3—C4	−1.7 (4)	C1—N2—C8—C9	114.0 (3)
C2—C3—C4—C5	−0.3 (4)	C7—N2—C8—C9	−69.7 (3)
C2—C3—C4—N3	178.0 (2)	N2—C8—C9—C10	−65.3 (3)
O2—N3—C4—C5	172.5 (2)	C8—C9—C10—C11	−177.1 (2)
O3—N3—C4—C5	−7.0 (4)	C9—C10—C11—C12	177.9 (3)
O2—N3—C4—C3	−5.8 (4)	C10—C11—C12—C13	−176.8 (3)
O3—N3—C4—C3	174.7 (2)	C11—C12—C13—C14	178.5 (3)
C3—C4—C5—C6	1.8 (4)	C12—C13—C14—C15	−176.4 (3)
N3—C4—C5—C6	−176.5 (2)	C13—C14—C15—C16	178.6 (3)
C4—C5—C6—C7	−1.2 (4)	C14—C15—C16—C17	−175.7 (3)
C1—N2—C7—C6	179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.92	2.784 (3)	168

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₅N₃O₃
M_r	319.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.4933 (2), 10.3063 (4), 16.1655 (6)
α, β, γ (°)	106.504 (2), 98.545 (2), 96.809 (2)
V (Å³)	855.21 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.06 × 0.04

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10701, 2971, 1600
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.175, 0.89
No. of reflections	2971
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.31

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.92	2.784 (3)	168

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank Université Sidi Mohamed Ben Abdallah, Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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