4,4′-Bipyridinium bis­(2-carboxy­pyridine-3-carboxyl­ate)

Soleimannejad, J.; Aghabozorg, H.; Morsali, A.; Hemmati, F.; Manteghi, F.

doi:10.1107/S1600536808042220

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o153

doi:10.1107/S1600536808042220

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4,4′-Bipyridinium bis(2-carboxypyridine-3-carboxylate)

Janet Soleimannejad,^a ^* Hossein Aghabozorg,^b Ali Morsali,^c Foruzan Hemmati ^d and Faranak Manteghi ^e

^aDepartment of Chemistry, Ilam University, Ilam, Iran, ^bFaculty of Chemistry, Tarbiat Moallem University, Tehran, Iran, ^cDepartment of Chemistry, School of Sciences, Tarbiat Modarres University, PO Box 14155-4838, Tehran, Iran, ^dFaculty of Chemistry, Payame Noor University (PNU), Abhar, Iran, and ^eDepartment of Chemistry, Iran University of Science and Technology, Tehran, Iran
^*Correspondence e-mail: janet_soleimannejad@yahoo.com

(Received 29 November 2008; accepted 11 December 2008; online 17 December 2008)

The title salt, C₁₀H₁₀N₂²⁺·2C₇H₄NO₄⁻ or (4,4′-bpyH₂)(py-2,3-dcH)₂, prepared by the reaction between pyridine-2,3-dicarboxylic acid (py-2,3-dcH₂) and 4,4′-bipyridine (4,4′-bpy), consists of two anions and one centrosymmetric dication. In the crystal, there are two strong O—H⋯O hydrogen bonds involving the two carboxylate groups, with an O⋯O distance of 2.478 (1) Å, and an N—H⋯N hydrogen bond between the anion and cation, with an N⋯N distance of 2.743 (1) Å. These interactions, along with other O—H⋯O and C—H⋯O hydrogen bonds, π–π stacking [centroid–centroid distances 3.621 (7) and 3.612 (7) Å] and ion pairing, lead to the formation of the three-dimensional structure.

Related literature

For proton-transfer ion pairs, see: Seethalakshmi et al. (2007 ); Manteghi et al. (2007 ); Aghabozorg, Manteghi & Ghadermazi (2008 ). For the use of ion pairs for the formation of metal organic frameworks, see: Aghabozorg, Manteghi & Sheshmani (2008 ). For hydrogen bonding, see: Desiraju & Steiner (1999 ).

Experimental

Crystal data

C₁₀H₁₀N₂²⁺·2C₇H₄NO₄⁻
M_r = 490.42
Monoclinic, P 2₁ /n
a = 6.6675 (2) Å
b = 13.7755 (5) Å
c = 11.5887 (4) Å
β = 106.310 (2)°
V = 1021.56 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 120 (2) K
0.33 × 0.25 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.904, T_max = 0.988
18931 measured reflections
2327 independent reflections
2053 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.105
S = 1.05
2327 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.85	1.90	2.7430 (14)	175
O4—H4A⋯O2ⁱ	0.85	1.64	2.4782 (12)	171
C3—H3⋯O4ⁱⁱ	0.95	2.40	3.2055 (15)	143
C4—H4⋯O2ⁱⁱⁱ	0.95	2.55	3.4324 (15)	155
C9—H9⋯O1^iv	0.95	2.41	3.3405 (15)	166
C11—H11⋯O1^v	0.95	2.52	3.4610 (15)	170
C12—H12⋯O3^v	0.95	2.19	2.9004 (15)	131
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+2; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042220/su2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042220/su2083Isup2.hkl

checkCIF report

Comment top

Up to now, pyridine-2,3-dicarboxylic acid has been used to synthesize a numer of proton transfer ion pairs, such as 1,4-Diazoniabicyclo[2.2.2]octane bis(3-carboxypyridine-2-carboxylate) 2.17-hydrate (Seethalakshmi et al., 2007), propane-1,3-diaminium pyridine-2,3-dicarboxylate monohydrate (Manteghi et al., 2007) and piperazinediium bis(2-carboxypyridine-3-carboxylate) (Aghabozorg, Manteghi & Ghadermazi, 2008). The last two have been used to synthesize some metal organic frameworks (Aghabozorg, Manteghi, Sheshmani, 2008) in which the acid acts as a mono- or dianionic fragment. In the title ion pair, (4,4'-bpyH₂)(py-2,3-dcH)₂, the centrosymmetric dicationic moiety is balanced by two acid moieties in the monoanionic form, as shown in Fig. 1.

In the crystal structure various O—H···O, N—H···N and C—H···O hydrogen bonds are present (Table 1 and Fig. 2). The N2—H2A···N1 hydrogen bond, classified as very strong (Desiraju & Steiner, 1999), links directly the cation and anion of the centrosymmetric unit, with a 5° deviation from linearity and a distance of 2.743 (4) Å.

There is also π-π stacking (Fig. 3) between the acid (N1/C1—C5) and the base (N2/C8—C12) rings with different symmetry codes (-x, 1 - y, 1 - z and 1 - x, 1 - y, 1 - z) at distances of 3.621 (7) and 3.612 (7) Å, respectively. As shown by the torsion angles, C2-C1-C6-O2 and C2-C1-C6-O1 [78.49 (14)° and -105.43 (3)°, respectively], it can be concluded that the carboxylate group, involving atoms O1 and O2, is almost perpendicular to the π-ring of the acid. However, torsion angles, C3-C2-C7-O4 and C3-C2-C7-O3 [15.5 (2)° and -162.6 (1)°, respectively], indicate that the carboxylate groups, involving atoms O3 and O4, are nearly coplanar with the ring.

Related literature top

For proton-transfer ion pairs, see: Seethalakshmi et al. (2007); Manteghi et al. (2007); Aghabozorg, Manteghi & Ghadermazi (2008). For the use of ion pairs for the formation of metal organic frameworks, see: Aghabozorg, Manteghi & Sheshmani (2008). For hydrogen bonding, see: Desiraju & Steiner (1999).

Experimental top

An aqueous solution (10 ml) of 4,4'-bipyridine (156 mg, 1 mmol) and pyridine-2,3-dicarboxylic acid (167 mg, 1 mmol) was refluxed for two hours. Yellow crystals of the title compound were obtained from the solution after two hours at room temperature.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the displacement ellipsoids drawn at the 50% proability level.
	Fig. 2. A view of the crystal packing diagram of the title compound with the hydrogen bonds shown as dashed lines.
	Fig. 3. The π-π stacking in the title compound, between acid (N1/C1—C5) and base (N2/C8—C12) rings with symmetry codes: right-hand-side = -x, 1 - y, 1 - z; left-hand-side = 1 - x, 1 - y, 1 - z.
	Fig. 4. The formation of the title compound.

4,4'-Bipyridinium bis(2-carboxypyridine-3-carboxylate) top

Crystal data top

C₁₀H₁₀N₂²⁺·2C₇H₄NO₄⁻	F(000) = 508
M_r = 490.42	D_x = 1.594 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7505 reflections
a = 6.6675 (2) Å	θ = 2.4–27.5°
b = 13.7755 (5) Å	µ = 0.12 mm⁻¹
c = 11.5887 (4) Å	T = 120 K
β = 106.310 (2)°	Block, yellow
V = 1021.56 (6) Å³	0.33 × 0.25 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2327 independent reflections
Radiation source: fine-focus sealed tube	2053 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.904, T_max = 0.988	k = −17→17
18931 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0592P)² + 0.4079P] where P = (F_o² + 2F_c²)/3
2327 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₀H₁₀N₂²⁺·2C₇H₄NO₄⁻	V = 1021.56 (6) Å³
M_r = 490.42	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.6675 (2) Å	µ = 0.12 mm⁻¹
b = 13.7755 (5) Å	T = 120 K
c = 11.5887 (4) Å	0.33 × 0.25 × 0.10 mm
β = 106.310 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2327 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2053 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.988	R_int = 0.028
18931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
2327 reflections	Δρ_min = −0.28 e Å⁻³
163 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
N1	0.27652 (15)	0.50895 (8)	0.56149 (9)	0.0150 (2)
N2	0.15565 (15)	0.51345 (8)	0.31494 (9)	0.0165 (2)
H2A	0.1890	0.5153	0.3913	0.020*
O1	0.38783 (15)	0.30360 (6)	0.50820 (8)	0.0223 (2)
O2	0.08964 (13)	0.29549 (6)	0.56245 (7)	0.0182 (2)
O3	0.45903 (15)	0.26665 (6)	0.77965 (8)	0.0227 (2)
O4	0.47246 (15)	0.35410 (6)	0.94390 (8)	0.0224 (2)
H4A	0.5120	0.2999	0.9777	0.027*
C1	0.31214 (17)	0.42864 (8)	0.63036 (10)	0.0135 (2)
C2	0.38515 (17)	0.43413 (8)	0.75593 (10)	0.0137 (2)
C3	0.41707 (18)	0.52530 (9)	0.80969 (11)	0.0155 (3)
H3	0.4647	0.5310	0.8947	0.019*
C4	0.37892 (18)	0.60781 (9)	0.73843 (11)	0.0166 (3)
H4	0.3994	0.6707	0.7735	0.020*
C5	0.31027 (18)	0.59644 (9)	0.61490 (11)	0.0161 (3)
H5	0.2860	0.6528	0.5658	0.019*
C6	0.26464 (18)	0.33299 (9)	0.56194 (10)	0.0151 (3)
C7	0.44097 (18)	0.34292 (8)	0.82870 (10)	0.0148 (2)
C8	0.13421 (18)	0.59568 (9)	0.25032 (11)	0.0177 (3)
H8	0.1612	0.6565	0.2904	0.021*
C9	0.07338 (19)	0.59273 (9)	0.12624 (11)	0.0170 (3)
H9	0.0595	0.6512	0.0812	0.020*
C10	0.03217 (17)	0.50302 (9)	0.06698 (10)	0.0148 (3)
C11	0.05390 (19)	0.41949 (9)	0.13730 (11)	0.0180 (3)
H11	0.0250	0.3576	0.1002	0.022*
C12	0.11771 (19)	0.42708 (9)	0.26137 (11)	0.0187 (3)
H12	0.1347	0.3699	0.3090	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0158 (5)	0.0161 (5)	0.0131 (5)	0.0009 (4)	0.0039 (4)	0.0014 (4)
N2	0.0177 (5)	0.0207 (5)	0.0106 (5)	−0.0012 (4)	0.0032 (4)	0.0010 (4)
O1	0.0308 (5)	0.0181 (5)	0.0215 (5)	0.0006 (4)	0.0130 (4)	−0.0027 (3)
O2	0.0197 (4)	0.0178 (4)	0.0156 (4)	−0.0025 (3)	0.0026 (3)	−0.0045 (3)
O3	0.0355 (5)	0.0131 (4)	0.0151 (4)	0.0017 (4)	0.0002 (4)	−0.0007 (3)
O4	0.0375 (5)	0.0165 (5)	0.0118 (4)	0.0072 (4)	0.0045 (4)	0.0034 (3)
C1	0.0128 (5)	0.0142 (5)	0.0136 (5)	0.0006 (4)	0.0038 (4)	0.0009 (4)
C2	0.0137 (5)	0.0143 (6)	0.0129 (5)	0.0005 (4)	0.0036 (4)	0.0002 (4)
C3	0.0163 (5)	0.0170 (6)	0.0128 (5)	0.0008 (4)	0.0035 (4)	−0.0006 (4)
C4	0.0183 (6)	0.0137 (6)	0.0174 (6)	0.0001 (4)	0.0045 (5)	−0.0016 (4)
C5	0.0164 (6)	0.0139 (6)	0.0180 (6)	0.0015 (4)	0.0048 (4)	0.0032 (4)
C6	0.0207 (6)	0.0143 (6)	0.0084 (5)	0.0023 (4)	0.0012 (4)	0.0020 (4)
C7	0.0147 (5)	0.0152 (6)	0.0130 (5)	−0.0013 (4)	0.0013 (4)	0.0000 (4)
C8	0.0200 (6)	0.0170 (6)	0.0163 (6)	−0.0001 (4)	0.0052 (5)	−0.0002 (4)
C9	0.0190 (6)	0.0165 (6)	0.0153 (6)	0.0009 (4)	0.0046 (4)	0.0027 (4)
C10	0.0120 (5)	0.0187 (6)	0.0135 (6)	−0.0009 (4)	0.0034 (4)	0.0016 (4)
C11	0.0218 (6)	0.0165 (6)	0.0146 (6)	−0.0036 (5)	0.0033 (5)	0.0001 (4)
C12	0.0213 (6)	0.0184 (6)	0.0156 (6)	−0.0028 (5)	0.0037 (5)	0.0035 (5)

Geometric parameters (Å, º) top

N1—C5	1.3446 (15)	C3—C4	1.3857 (16)
N1—C1	1.3457 (15)	C3—H3	0.9500
N2—C12	1.3330 (16)	C4—C5	1.3840 (17)
N2—C8	1.3432 (16)	C4—H4	0.9500
N2—H2A	0.8501	C5—H5	0.9500
O1—C6	1.2303 (15)	C8—C9	1.3807 (17)
O2—C6	1.2775 (15)	C8—H8	0.9500
O3—C7	1.2165 (15)	C9—C10	1.4030 (17)
O4—C7	1.3009 (14)	C9—H9	0.9500
O4—H4A	0.8501	C10—C11	1.3938 (17)
C1—C2	1.4009 (16)	C10—C10ⁱ	1.492 (2)
C1—C6	1.5245 (16)	C11—C12	1.3841 (17)
C2—C3	1.3915 (16)	C11—H11	0.9500
C2—C7	1.5007 (15)	C12—H12	0.9500

C5—N1—C1	119.02 (10)	O1—C6—C1	118.49 (11)
C12—N2—C8	121.10 (10)	O2—C6—C1	113.81 (10)
C12—N2—H2A	118.2	O3—C7—O4	124.97 (11)
C8—N2—H2A	120.7	O3—C7—C2	120.13 (10)
C7—O4—H4A	108.0	O4—C7—C2	114.88 (10)
N1—C1—C2	121.58 (10)	N2—C8—C9	120.66 (11)
N1—C1—C6	115.20 (10)	N2—C8—H8	119.7
C2—C1—C6	123.21 (10)	C9—C8—H8	119.7
C3—C2—C1	118.59 (10)	C8—C9—C10	119.71 (11)
C3—C2—C7	121.43 (10)	C8—C9—H9	120.1
C1—C2—C7	119.84 (10)	C10—C9—H9	120.1
C4—C3—C2	119.61 (11)	C11—C10—C9	117.85 (11)
C4—C3—H3	120.2	C11—C10—C10ⁱ	120.96 (13)
C2—C3—H3	120.2	C9—C10—C10ⁱ	121.19 (13)
C5—C4—C3	118.40 (11)	C12—C11—C10	119.75 (11)
C5—C4—H4	120.8	C12—C11—H11	120.1
C3—C4—H4	120.8	C10—C11—H11	120.1
N1—C5—C4	122.79 (11)	N2—C12—C11	120.93 (11)
N1—C5—H5	118.6	N2—C12—H12	119.5
C4—C5—H5	118.6	C11—C12—H12	119.5
O1—C6—O2	127.57 (11)

C5—N1—C1—C2	−0.59 (17)	C2—C1—C6—O2	78.49 (14)
C5—N1—C1—C6	178.63 (10)	C3—C2—C7—O3	−162.59 (11)
N1—C1—C2—C3	1.26 (17)	C1—C2—C7—O3	13.12 (17)
C6—C1—C2—C3	−177.90 (10)	C3—C2—C7—O4	15.52 (16)
N1—C1—C2—C7	−174.57 (10)	C1—C2—C7—O4	−168.77 (11)
C6—C1—C2—C7	6.27 (17)	C12—N2—C8—C9	−0.43 (18)
C1—C2—C3—C4	−0.83 (17)	N2—C8—C9—C10	0.43 (18)
C7—C2—C3—C4	174.93 (11)	C8—C9—C10—C11	0.31 (18)
C2—C3—C4—C5	−0.21 (17)	C8—C9—C10—C10ⁱ	−179.48 (13)
C1—N1—C5—C4	−0.53 (18)	C9—C10—C11—C12	−1.05 (18)
C3—C4—C5—N1	0.93 (18)	C10ⁱ—C10—C11—C12	178.75 (13)
N1—C1—C6—O1	75.36 (14)	C8—N2—C12—C11	−0.34 (18)
C2—C1—C6—O1	−105.43 (13)	C10—C11—C12—N2	1.09 (19)
N1—C1—C6—O2	−100.72 (12)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.85	1.90	2.7430 (14)	175
O4—H4A···O2ⁱⁱ	0.85	1.64	2.4782 (12)	171
C3—H3···O4ⁱⁱⁱ	0.95	2.40	3.2055 (15)	143
C4—H4···O2^iv	0.95	2.55	3.4324 (15)	155
C9—H9···O1^v	0.95	2.41	3.3405 (15)	166
C11—H11···O1^vi	0.95	2.52	3.4610 (15)	170
C12—H12···O3^vi	0.95	2.19	2.9004 (15)	131

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂²⁺·2C₇H₄NO₄⁻
M_r	490.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	6.6675 (2), 13.7755 (5), 11.5887 (4)
β (°)	106.310 (2)
V (Å³)	1021.56 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.33 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.904, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	18931, 2327, 2053
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.105, 1.05
No. of reflections	2327
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.85	1.90	2.7430 (14)	174.9
O4—H4A···O2ⁱ	0.85	1.64	2.4782 (12)	170.9
C3—H3···O4ⁱⁱ	0.95	2.40	3.2055 (15)	143.0
C4—H4···O2ⁱⁱⁱ	0.95	2.55	3.4324 (15)	155.0
C9—H9···O1^iv	0.95	2.41	3.3405 (15)	166.0
C11—H11···O1^v	0.95	2.52	3.4610 (15)	170.0
C12—H12···O3^v	0.95	2.19	2.9004 (15)	131.0

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

Acknowledgements

The authors are grateful to Ilam University for financial support of this work.

References

Aghabozorg, H., Manteghi, F. & Ghadermazi, M. (2008). Acta Cryst. E64, o230. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SAINT and SMART . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc. Google Scholar
Manteghi, F., Ghadermazi, M. & Aghabozorg, H. (2007). Acta Cryst. E63, o2809. Web of Science CSD CrossRef IUCr Journals Google Scholar
Seethalakshmi, P. G., Ramadevi, P., Kumaresan, S. & Harrison, W. T. A. (2007). Acta Cryst. E63, o4837. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar