Piperazine-1,4-diium pyridine-2,3-dicarboxyl­ate methanol monosolvate

Manteghi, F.; Ghadermazi, M.; Kakaei, N.

doi:10.1107/S1600536811012384

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1122

doi:10.1107/S1600536811012384

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Piperazine-1,4-diium pyridine-2,3-dicarboxylate methanol monosolvate †

Faranak Manteghi,^a Mohammad Ghadermazi ^b ^* and Nasrin Kakaei ^b

^aDepartment of Chemistry, Iran University of Science and Technology, Tehran, Iran, and ^bDepartment of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran
^*Correspondence e-mail: mghadermazi@yahoo.com

(Received 16 March 2011; accepted 3 April 2011; online 13 April 2011)

The title solvated molecular salt, C₄H₁₂N₂²⁺·C₇H₃NO₄²⁻·CH₃OH or (pipzH₂)(py-2,3-dc)·MeOH, was prepared by the reaction of pyridine-2,3-dicarboxylic acid (py-2,3-dcH₂) and piperazine (pipz) in methanol (MeOH) as solvent. One of the two carboxylate groups of the acid fragment is nearly perpendicular to the pyridine ring and the other is almost in its plane [C—C—C—O torsion angles = −85.50 (11) and 88.07 (11)° and N—C—C—O torsion angles = −176.31 (8) and 5.41 (13)°]. In the crystal, the components are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For similar ion pairs, see: Aghabozorg, Manteghi & Ghadermazi (2008 ); Aghabozorg, Manteghi & Sheshmani (2008 ). For related metal complexes, see: Barszcz et al. (2010 ); Li & Li (2004 ).

Experimental

Crystal data

C₄H₁₂N₂²⁺·C₇H₃NO₄²⁻·CH₄O
M_r = 285.30
Monoclinic, P 2₁ /n
a = 8.2541 (6) Å
b = 11.8988 (8) Å
c = 13.8197 (9) Å
β = 90.288 (2)°
V = 1357.27 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer
16044 measured reflections
3579 independent reflections
3189 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.085
S = 1.03
3579 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.90	1.74	2.6257 (11)	168
N2—H2B⋯O2	0.90	1.89	2.7274 (11)	155
N3—H3A⋯O1ⁱⁱ	0.90	1.85	2.7379 (11)	169
N3—H3B⋯O3ⁱⁱⁱ	0.90	1.86	2.7393 (11)	166
O5—H5A⋯O1	0.85	1.84	2.6867 (10)	171
C3—H3⋯O5^iv	0.95	2.41	3.3163 (13)	159
Symmetry codes: (i) -x, -y+2, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x-1, y, z.

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: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012384/om2416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012384/om2416Isup2.hkl

checkCIF report

Comment top

Pyridine-2,3-dicarboxylic acid is remarkably attractive for its flexible and variable coordination modes to construct polymeric architecture. It can act as monodicarboxylate chelating anion, or tridentate coordinating anion with acid hydrogen on nitrogen and doubly deprotonated, tridentate dicarboxylate anion (py-2,3-dc) and even in Mn(II) complexes as tetradenatate and pentadentate ligands (Barszcz et al., 2010; Li & Li, 2004). Preparation of ion pairs with the acid increases the chance of its coordination to metals. Therefore, in our work to obtain proton transfer ion pairs, we have reviewed many ion pairs and their metal complexes (Aghabozorg, Manteghi & Sheshmani, 2008). Also, we have reported a similar ion pair formulated as (pipzH₂)(pydcH)₂, (Aghabozorg, Manteghi & Ghadermazi, 2008). The title structure, as shown in Fig. 1, has an asymmetric unit constructed by (pipzH₂)²⁺ and (py-2,3-dc)^2– and a neutral methanol molecule with two hydrogen bonds. There are varieties of other strong and weak hydrogen bonds in the structure, shown in Table 1. Also, a C–O···π stacking, between C6–O2 and N1/C1-C5 ring (-x, -y + 2, -z) with the distance of 3.5240 (9) Å, and a C–H···π stacking, between C12–H1A and N1/C1-C5 ring (x +1/2, -y +3/2, z -1/2), with the distance of 2.791 (1) Å, shown in Fig. 2 are observed.

Related literature top

For similar ion pairs, see: Aghabozorg, Manteghi & Ghadermazi (2008); Aghabozorg, Manteghi & Sheshmani (2008). For related metal complexes, see: Barszcz et al. (2010); Li & Li (2004).

Experimental top

The title compound was synthesized via reaction of 1670 mg (10 mmol) pyridine-2,3-dicarboxylic acid with 860 mg (10 mmol) piperazine in a methanol solution (60 ml). The obtained white precipitate was filtered out and dissolved in water to recrystallize. Colorless crystals of the title compound were obtained after 14 days.

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: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (pipzH₂)(py-2,3-dc).MeOH
	Fig. 2. The C–H···π stacking between C12–H1A of methanol and N1/C1-C5 ring of py-2,3-dc.

Piperazine-1,4-diium pyridine-2,3-dicarboxylate methanol monosolvate top

Crystal data top

C₄H₁₂N₂²⁺·C₇H₃NO₄²⁻·CH₄O	F(000) = 608
M_r = 285.30	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7483 reflections
a = 8.2541 (6) Å	θ = 2.3–28.1°
b = 11.8988 (8) Å	µ = 0.11 mm⁻¹
c = 13.8197 (9) Å	T = 100 K
β = 90.288 (2)°	Prism, colourless
V = 1357.27 (16) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	3189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 29.0°, θ_min = 2.3°
Detector resolution: 8.3 pixels mm^-1	h = −11→11
ϕ and ω scans	k = −16→16
16044 measured reflections	l = −18→18
3579 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.035P)² + 0.650P] where P = (F_o² + 2F_c²)/3
3579 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₄H₁₂N₂²⁺·C₇H₃NO₄²⁻·CH₄O	V = 1357.27 (16) Å³
M_r = 285.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2541 (6) Å	µ = 0.11 mm⁻¹
b = 11.8988 (8) Å	T = 100 K
c = 13.8197 (9) Å	0.25 × 0.20 × 0.10 mm
β = 90.288 (2)°

Data collection top

Bruker SMART APEXII diffractometer	3189 reflections with I > 2σ(I)
16044 measured reflections	R_int = 0.023
3579 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
3579 reflections	Δρ_min = −0.21 e Å⁻³
182 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

	x	y	z	U_iso*/U_eq
O1	0.16285 (8)	0.76486 (6)	0.03344 (5)	0.01401 (15)
O2	0.21626 (9)	0.91599 (6)	0.12414 (6)	0.01918 (16)
O3	−0.13943 (9)	0.61040 (6)	0.03291 (5)	0.01666 (16)
O4	−0.11791 (9)	0.70279 (6)	−0.10648 (5)	0.01627 (15)
N1	−0.09833 (10)	0.97903 (7)	0.11968 (6)	0.01339 (17)
N2	0.17152 (10)	1.11819 (7)	0.21302 (6)	0.01264 (16)
H2A	0.1410	1.1746	0.1735	0.015*
H2B	0.1538	1.0523	0.1828	0.015*
N3	0.31476 (10)	1.05117 (7)	0.39424 (6)	0.01304 (16)
H3A	0.3349	1.1189	0.4206	0.016*
H3B	0.3473	0.9987	0.4371	0.016*
C1	−0.05754 (11)	0.88142 (8)	0.07675 (6)	0.01078 (17)
C2	−0.17210 (11)	0.80866 (8)	0.03586 (7)	0.01165 (18)
C3	−0.33567 (12)	0.83780 (9)	0.04316 (7)	0.01506 (19)
H3	−0.4169	0.7896	0.0175	0.018*
C4	−0.37860 (12)	0.93756 (9)	0.08809 (7)	0.0166 (2)
H4	−0.4891	0.9585	0.0943	0.020*
C5	−0.25545 (12)	1.00615 (9)	0.12379 (7)	0.01563 (19)
H5	−0.2845	1.0758	0.1525	0.019*
C6	0.12243 (11)	0.85332 (8)	0.07816 (7)	0.01183 (18)
C7	−0.13540 (11)	0.69936 (8)	−0.01603 (7)	0.01243 (18)
C8	0.07828 (12)	1.12692 (9)	0.30451 (7)	0.01538 (19)
H8A	−0.0383	1.1149	0.2908	0.018*
H8B	0.0914	1.2032	0.3320	0.018*
C9	0.34843 (12)	1.13038 (8)	0.23146 (7)	0.01367 (18)
H9A	0.3709	1.2059	0.2584	0.016*
H9B	0.4080	1.1231	0.1698	0.016*
C10	0.40670 (12)	1.04139 (8)	0.30194 (7)	0.01438 (19)
H10A	0.3901	0.9658	0.2737	0.017*
H10B	0.5239	1.0513	0.3148	0.017*
C11	0.13684 (12)	1.04015 (9)	0.37760 (7)	0.0162 (2)
H11A	0.0790	1.0508	0.4395	0.019*
H11B	0.1121	0.9637	0.3533	0.019*
O5	0.39165 (9)	0.71135 (8)	−0.09625 (6)	0.02485 (19)
H5A	0.3255	0.7344	−0.0537	0.037*
C12	0.29401 (15)	0.65794 (12)	−0.16692 (9)	0.0302 (3)
H1A	0.3427	0.6679	−0.2309	0.045*
H1B	0.1855	0.6913	−0.1667	0.045*
H1C	0.2861	0.5776	−0.1522	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0156 (3)	0.0103 (3)	0.0162 (3)	0.0017 (2)	0.0019 (3)	−0.0011 (3)
O2	0.0139 (3)	0.0188 (4)	0.0248 (4)	0.0001 (3)	−0.0031 (3)	−0.0083 (3)
O3	0.0236 (4)	0.0110 (3)	0.0153 (3)	−0.0009 (3)	−0.0041 (3)	0.0011 (3)
O4	0.0233 (4)	0.0130 (3)	0.0124 (3)	0.0028 (3)	−0.0019 (3)	−0.0007 (3)
N1	0.0154 (4)	0.0117 (4)	0.0130 (4)	0.0005 (3)	0.0011 (3)	−0.0010 (3)
N2	0.0152 (4)	0.0111 (4)	0.0116 (4)	0.0003 (3)	−0.0022 (3)	0.0000 (3)
N3	0.0168 (4)	0.0105 (4)	0.0118 (4)	−0.0007 (3)	−0.0025 (3)	0.0007 (3)
C1	0.0128 (4)	0.0103 (4)	0.0093 (4)	0.0003 (3)	0.0007 (3)	0.0009 (3)
C2	0.0143 (4)	0.0109 (4)	0.0097 (4)	0.0003 (3)	−0.0006 (3)	0.0008 (3)
C3	0.0135 (4)	0.0173 (5)	0.0144 (4)	−0.0005 (3)	−0.0013 (3)	−0.0005 (4)
C4	0.0134 (4)	0.0201 (5)	0.0163 (4)	0.0037 (4)	0.0002 (3)	0.0002 (4)
C5	0.0181 (5)	0.0136 (4)	0.0152 (4)	0.0032 (4)	0.0023 (3)	−0.0016 (3)
C6	0.0132 (4)	0.0111 (4)	0.0112 (4)	0.0005 (3)	0.0006 (3)	0.0015 (3)
C7	0.0117 (4)	0.0115 (4)	0.0141 (4)	0.0001 (3)	−0.0035 (3)	−0.0015 (3)
C8	0.0142 (4)	0.0172 (5)	0.0148 (4)	0.0009 (4)	0.0003 (3)	0.0002 (4)
C9	0.0142 (4)	0.0137 (4)	0.0132 (4)	−0.0004 (3)	−0.0002 (3)	0.0007 (3)
C10	0.0154 (4)	0.0146 (4)	0.0130 (4)	0.0021 (3)	−0.0011 (3)	−0.0002 (3)
C11	0.0160 (5)	0.0168 (5)	0.0159 (4)	−0.0040 (4)	−0.0006 (3)	0.0028 (4)
O5	0.0159 (4)	0.0345 (5)	0.0242 (4)	−0.0027 (3)	0.0035 (3)	−0.0117 (3)
C12	0.0239 (6)	0.0398 (7)	0.0269 (6)	−0.0016 (5)	0.0002 (5)	−0.0160 (5)

Geometric parameters (Å, º) top

O1—C6	1.2662 (12)	C3—H3	0.9500
O2—C6	1.2469 (12)	C4—C5	1.3920 (14)
O3—C7	1.2566 (12)	C4—H4	0.9500
O4—C7	1.2597 (12)	C5—H5	0.9500
N1—C5	1.3379 (13)	C8—C11	1.5215 (14)
N1—C1	1.3477 (12)	C8—H8A	0.9900
N2—C8	1.4871 (12)	C8—H8B	0.9900
N2—C9	1.4881 (12)	C9—C10	1.5155 (13)
N2—H2A	0.9001	C9—H9A	0.9900
N2—H2B	0.9001	C9—H9B	0.9900
N3—C11	1.4911 (13)	C10—H10A	0.9900
N3—C10	1.4920 (12)	C10—H10B	0.9900
N3—H3A	0.9000	C11—H11A	0.9900
N3—H3B	0.9001	C11—H11B	0.9900
C1—C2	1.3992 (13)	O5—C12	1.4139 (14)
C1—C6	1.5227 (13)	O5—H5A	0.8500
C2—C3	1.3981 (13)	C12—H1A	0.9800
C2—C7	1.5164 (13)	C12—H1B	0.9800
C3—C4	1.3864 (14)	C12—H1C	0.9800

C5—N1—C1	118.09 (8)	O4—C7—C2	117.75 (8)
C8—N2—C9	111.05 (7)	N2—C8—C11	110.67 (8)
C8—N2—H2A	108.6	N2—C8—H8A	109.5
C9—N2—H2A	107.6	C11—C8—H8A	109.5
C8—N2—H2B	111.9	N2—C8—H8B	109.5
C9—N2—H2B	108.8	C11—C8—H8B	109.5
H2A—N2—H2B	108.9	H8A—C8—H8B	108.1
C11—N3—C10	111.47 (7)	N2—C9—C10	110.48 (8)
C11—N3—H3A	108.7	N2—C9—H9A	109.6
C10—N3—H3A	108.9	C10—C9—H9A	109.6
C11—N3—H3B	109.3	N2—C9—H9B	109.6
C10—N3—H3B	110.9	C10—C9—H9B	109.6
H3A—N3—H3B	107.5	H9A—C9—H9B	108.1
N1—C1—C2	122.77 (9)	N3—C10—C9	109.50 (8)
N1—C1—C6	115.44 (8)	N3—C10—H10A	109.8
C2—C1—C6	121.77 (8)	C9—C10—H10A	109.8
C3—C2—C1	117.92 (9)	N3—C10—H10B	109.8
C3—C2—C7	116.24 (8)	C9—C10—H10B	109.8
C1—C2—C7	125.84 (8)	H10A—C10—H10B	108.2
C4—C3—C2	119.59 (9)	N3—C11—C8	110.61 (8)
C4—C3—H3	120.2	N3—C11—H11A	109.5
C2—C3—H3	120.2	C8—C11—H11A	109.5
C3—C4—C5	118.22 (9)	N3—C11—H11B	109.5
C3—C4—H4	120.9	C8—C11—H11B	109.5
C5—C4—H4	120.9	H11A—C11—H11B	108.1
N1—C5—C4	123.36 (9)	C12—O5—H5A	104.9
N1—C5—H5	118.3	O5—C12—H1A	109.5
C4—C5—H5	118.3	O5—C12—H1B	109.5
O2—C6—O1	125.55 (9)	H1A—C12—H1B	109.5
O2—C6—C1	118.59 (8)	O5—C12—H1C	109.5
O1—C6—C1	115.84 (8)	H1A—C12—H1C	109.5
O3—C7—O4	124.39 (9)	H1B—C12—H1C	109.5
O3—C7—C2	117.52 (8)

C5—N1—C1—C2	0.66 (14)	N1—C1—C6—O1	−176.31 (8)
C5—N1—C1—C6	−177.60 (8)	C2—C1—C6—O1	5.41 (13)
N1—C1—C2—C3	−2.12 (14)	C3—C2—C7—O3	−85.50 (11)
C6—C1—C2—C3	176.03 (8)	C1—C2—C7—O3	94.23 (12)
N1—C1—C2—C7	178.16 (9)	C3—C2—C7—O4	88.07 (11)
C6—C1—C2—C7	−3.69 (14)	C1—C2—C7—O4	−92.20 (12)
C1—C2—C3—C4	1.40 (14)	C9—N2—C8—C11	−56.46 (10)
C7—C2—C3—C4	−178.84 (9)	C8—N2—C9—C10	58.30 (10)
C2—C3—C4—C5	0.61 (15)	C11—N3—C10—C9	57.68 (10)
C1—N1—C5—C4	1.56 (15)	N2—C9—C10—N3	−58.17 (10)
C3—C4—C5—N1	−2.20 (15)	C10—N3—C11—C8	−56.39 (11)
N1—C1—C6—O2	5.41 (13)	N2—C8—C11—N3	55.14 (11)
C2—C1—C6—O2	−172.86 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.90	1.74	2.6257 (11)	168
N2—H2B···O2	0.90	1.89	2.7274 (11)	155
N3—H3A···O1ⁱⁱ	0.90	1.85	2.7379 (11)	169
N3—H3B···O3ⁱⁱⁱ	0.90	1.86	2.7393 (11)	166
O5—H5A···O1	0.85	1.84	2.6867 (10)	171
C3—H3···O5^iv	0.95	2.41	3.3163 (13)	159

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₄H₁₂N₂²⁺·C₇H₃NO₄²⁻·CH₄O
M_r	285.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.2541 (6), 11.8988 (8), 13.8197 (9)
β (°)	90.288 (2)
V (Å³)	1357.27 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16044, 3579, 3189
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.085, 1.03
No. of reflections	3579
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.90	1.74	2.6257 (11)	168
N2—H2B···O2	0.90	1.89	2.7274 (11)	155
N3—H3A···O1ⁱⁱ	0.90	1.85	2.7379 (11)	169
N3—H3B···O3ⁱⁱⁱ	0.90	1.86	2.7393 (11)	166
O5—H5A···O1	0.85	1.84	2.6867 (10)	171
C3—H3···O5^iv	0.95	2.41	3.3163 (13)	159

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) x−1, y, z.

Footnotes

†In memory of our great professor, Dr Hossein Aghabozorg, who passed away recently.

Acknowledgements

We acknowledge financial support of this work by the Iran University of Science and Technology and the University of Kurdistan.

References

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