(4,4′-Dimethyl-2,2′-bipyridine-κ2N,N′)(dimethyl sulfoxide-κO)diiodidozinc(II)

Yousefi, M.

doi:10.1107/S1600536810046763

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1594-m1595

https://doi.org/10.1107/S1600536810046763

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(4,4′-Dimethyl-2,2′-bipyridine-κ²N,N′)(dimethyl sulfoxide-κO)diiodidozinc(II)

Mohammad Yousefi ^a ^*

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: myousefi50@yahoo.com

(Received 4 November 2010; accepted 11 November 2010; online 17 November 2010)

In the title compound, [ZnI₂(C₁₂H₁₂N₂)(C₂H₆OS)], the Zn^II ion is coordinated by two N atoms from a 4,4′-dimethyl-2,2′-bipyridine ligand, one O atom from a dimethyl sulfoxide molecule and two I atoms in a distorted trigonal-bipyramidal geometry. Intramolecular C—H⋯O hydrogen bonds and intermolecular π–π stacking interactions between the pyridine rings [centroid–centroid distances = 3.637 (4) and 3.818 (4) Å] are present in the crystal structure.

Related literature

For metal complexes of 4,4′-dimethyl-2,2′-bipyridine, see: Ahmadi et al. (2008 ); Alizadeh et al. (2010 ); Amani et al. (2009 ); Bellusci et al. (2008 ); Hojjat Kashani et al. (2008 ); Kalateh et al. (2008 , 2010 ); Sakamoto et al. (2004 ); Sofetis et al. (2006 ); Willett et al. (2001 ); Yoshikawa et al. (2003 ); Yousefi et al. (2008 ).

Experimental

Crystal data

[ZnI₂(C₁₂H₁₂N₂)(C₂H₆OS)]
M_r = 581.56
Monoclinic, P 2₁ /c
a = 8.6173 (7) Å
b = 15.5424 (11) Å
c = 14.8976 (10) Å
β = 102.908 (6)°
V = 1944.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.54 mm⁻¹
T = 298 K
0.40 × 0.20 × 0.10 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.350, T_max = 0.636
21034 measured reflections
5243 independent reflections
4246 reflections with I > 2σ(I)
R_int = 0.113

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.202
S = 1.20
5243 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 2.11 e Å⁻³
Δρ_min = −2.87 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—N1	2.135 (5)
Zn1—N2	2.167 (6)
Zn1—O1	2.112 (5)
Zn1—I1	2.6199 (9)
Zn1—I2	2.6944 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.93	2.41	2.938 (9)	116

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046763/hy2375sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046763/hy2375Isup2.hkl

checkCIF report

Comment top

4,4'-Dimethyl-2,2'-bipyridine (4,4'-dmbipy) is a good bidentate ligand and numerous complexes with 4,4'-dmbipy have been prepared, such as that of mercury (Kalateh et al., 2008; Yousefi et al., 2008), indium (Ahmadi et al., 2008), iron (Amani et al., 2009), platinum (Hojjat Kashani et al., 2008), manganese (Sakamoto et al., 2004), silver (Bellusci et al., 2008), gallium (Sofetis et al., 2006), copper (Willett et al., 2001), zinc (Alizadeh et al., 2010), cadmium (Kalateh et al., 2010) and iridium (Yoshikawa et al., 2003). Here, we report the synthesis and structure of the title compound.

In the title compound (Fig. 1), the Zn^II ion is coordinated by two N atoms from a 4,4'-dmbipy ligand, one O atom from a dimethyl sulfoxide molecule and two I^- anions in a distorted trigonal-bipyramidal geometry. The Zn—I, Zn—O and Zn—N bond lengths are collected in Table 1. In the crystal structure, intramolecular C—H···O hydrogen bonds (Table 2) and intermolecular π–π stacking interactions (Fig. 2) between the pyridine rings, Cg2···Cg2ⁱ and Cg2···Cg3ⁱⁱ [symmetry codes: (i) 1-x, -y, 1-z; (ii) -x, -y, 1-z; Cg2 and Cg3 are the centroids of the N1, C1, C2, C3, C5, C6 ring and N2, C7, C8, C9, C11, C12 ring, respectively] may stabilize the structure, with centroid–centroid distances of 3.637 (4) and 3.818 (4) Å.

Related literature top

For metal complexes of 4,4'-dimethyl-2,2'-bipyridine, see: Ahmadi et al. (2008); Alizadeh et al. (2010); Amani et al. (2009); Bellusci et al. (2008); Hojjat Kashani et al. (2008); Kalateh et al. (2008, 2010); Sakamoto et al. (2004); Sofetis et al. (2006); Willett et al. (2001); Yoshikawa et al. (2003); Yousefi et al. (2008).

Experimental top

For the preparation of the title compound, a solution of 4,4'-dmbipy (0.15 g, 0.80 mmol) in methanol (10 ml) was added to a solution of ZnI₂ (0.25 g, 0.80 mmol) in methanol (5 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.34 g, 73.1%).

Structure description top

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing diagram for the title compound.

(4,4'-Dimethyl-2,2'-bipyridine-κ²N,N')(dimethyl sulfoxide-κO) diiodidozinc(II) top

Crystal data top

[ZnI₂(C₁₂H₁₂N₂)(C₂H₆OS)]	F(000) = 1104
M_r = 581.56	D_x = 1.986 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21034 reflections
a = 8.6173 (7) Å	θ = 2.4–29.2°
b = 15.5424 (11) Å	µ = 4.54 mm⁻¹
c = 14.8976 (10) Å	T = 298 K
β = 102.908 (6)°	Block, colorless
V = 1944.9 (3) Å³	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	5243 independent reflections
Radiation source: fine-focus sealed tube	4246 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.113
φ and ω scans	θ_max = 29.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.350, T_max = 0.636	k = −21→21
21034 measured reflections	l = −20→19

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.1105P)² + 1.119P] where P = (F_o² + 2F_c²)/3
5243 reflections	(Δ/σ)_max = 0.006
191 parameters	Δρ_max = 2.11 e Å⁻³
0 restraints	Δρ_min = −2.87 e Å⁻³

Crystal data top

[ZnI₂(C₁₂H₁₂N₂)(C₂H₆OS)]	V = 1944.9 (3) Å³
M_r = 581.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6173 (7) Å	µ = 4.54 mm⁻¹
b = 15.5424 (11) Å	T = 298 K
c = 14.8976 (10) Å	0.40 × 0.20 × 0.10 mm
β = 102.908 (6)°

Data collection top

Bruker APEX CCD diffractometer	5243 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4246 reflections with I > 2σ(I)
T_min = 0.350, T_max = 0.636	R_int = 0.113
21034 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.202	H-atom parameters constrained
S = 1.20	Δρ_max = 2.11 e Å⁻³
5243 reflections	Δρ_min = −2.87 e Å⁻³
191 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.3959 (9)	0.0849 (4)	0.5994 (5)	0.0499 (15)
H1	0.4491	0.1110	0.6537	0.060*
C2	0.4035 (10)	0.1229 (5)	0.5175 (5)	0.0558 (18)
H2	0.4613	0.1734	0.5171	0.067*
C3	0.3249 (8)	0.0859 (4)	0.4355 (5)	0.0434 (13)
C4	0.3297 (12)	0.1243 (6)	0.3445 (5)	0.060 (2)
H4C	0.2999	0.0816	0.2972	0.072*
H4B	0.4356	0.1442	0.3456	0.072*
H4A	0.2568	0.1718	0.3320	0.072*
C5	0.2391 (8)	0.0114 (4)	0.4415 (4)	0.0404 (12)
H5	0.1819	−0.0146	0.3880	0.049*
C6	0.2382 (7)	−0.0246 (4)	0.5263 (4)	0.0348 (11)
C7	0.1490 (7)	−0.1048 (4)	0.5361 (4)	0.0371 (11)
C8	0.0708 (8)	−0.1531 (5)	0.4614 (4)	0.0444 (13)
H8	0.0759	−0.1363	0.4022	0.053*
C9	−0.0137 (9)	−0.2252 (5)	0.4731 (5)	0.0520 (16)
C10	−0.0965 (13)	−0.2786 (6)	0.3928 (7)	0.072 (2)
H10C	−0.1468	−0.3269	0.4146	0.087*
H10B	−0.0202	−0.2987	0.3595	0.087*
H10A	−0.1755	−0.2443	0.3528	0.087*
C11	−0.0155 (10)	−0.2477 (5)	0.5633 (6)	0.0578 (18)
H11	−0.0723	−0.2957	0.5749	0.069*
C12	0.0667 (11)	−0.1988 (5)	0.6351 (5)	0.0563 (18)
H12	0.0660	−0.2157	0.6949	0.068*
C13	0.573 (3)	0.1599 (8)	0.8800 (9)	0.148 (9)
H13A	0.4826	0.1882	0.8428	0.178*
H13B	0.6632	0.1665	0.8523	0.178*
H13C	0.5975	0.1849	0.9404	0.178*
C14	0.7238 (12)	0.0134 (10)	0.9372 (7)	0.093 (4)
H14A	0.7977	0.0373	0.9044	0.112*
H14B	0.7258	−0.0482	0.9334	0.112*
H14C	0.7531	0.0307	1.0006	0.112*
N1	0.3148 (6)	0.0114 (3)	0.6051 (3)	0.0390 (10)
N2	0.1480 (7)	−0.1279 (4)	0.6227 (3)	0.0408 (11)
O1	0.4955 (6)	0.0209 (4)	0.7891 (3)	0.0512 (11)
Zn1	0.28482 (9)	−0.04667 (5)	0.72994 (5)	0.0401 (2)
I1	0.07682 (6)	0.04536 (4)	0.79226 (3)	0.05824 (19)
I2	0.37974 (8)	−0.18094 (4)	0.84331 (4)	0.0642 (2)
S1	0.5317 (2)	0.05061 (13)	0.88831 (11)	0.0482 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.057 (4)	0.047 (3)	0.043 (3)	−0.012 (3)	0.005 (3)	−0.002 (3)
C2	0.070 (5)	0.052 (4)	0.046 (4)	−0.016 (3)	0.013 (3)	0.003 (3)
C3	0.045 (3)	0.046 (3)	0.039 (3)	−0.005 (3)	0.010 (2)	0.005 (2)
C4	0.079 (5)	0.064 (4)	0.042 (4)	−0.011 (4)	0.021 (4)	0.012 (3)
C5	0.046 (3)	0.049 (3)	0.027 (2)	0.001 (3)	0.009 (2)	0.000 (2)
C6	0.035 (3)	0.040 (3)	0.030 (2)	−0.001 (2)	0.009 (2)	−0.002 (2)
C7	0.038 (3)	0.044 (3)	0.030 (3)	0.001 (2)	0.009 (2)	0.004 (2)
C8	0.046 (3)	0.052 (3)	0.036 (3)	−0.009 (3)	0.012 (2)	−0.001 (3)
C9	0.050 (4)	0.057 (4)	0.049 (4)	−0.012 (3)	0.009 (3)	0.001 (3)
C10	0.075 (6)	0.073 (5)	0.068 (5)	−0.025 (5)	0.014 (4)	−0.009 (4)
C11	0.058 (4)	0.052 (4)	0.064 (5)	−0.010 (3)	0.016 (3)	0.012 (3)
C12	0.065 (5)	0.057 (4)	0.048 (4)	−0.007 (3)	0.014 (3)	0.018 (3)
C13	0.29 (3)	0.070 (7)	0.058 (6)	−0.031 (11)	−0.023 (10)	−0.004 (5)
C14	0.048 (4)	0.171 (12)	0.055 (5)	0.020 (6)	0.000 (4)	−0.011 (7)
N1	0.038 (2)	0.046 (3)	0.032 (2)	−0.004 (2)	0.0059 (19)	0.000 (2)
N2	0.041 (3)	0.051 (3)	0.031 (2)	−0.002 (2)	0.0088 (19)	0.006 (2)
O1	0.045 (2)	0.078 (3)	0.030 (2)	−0.008 (2)	0.0059 (18)	−0.003 (2)
Zn1	0.0420 (4)	0.0511 (4)	0.0273 (3)	0.0043 (3)	0.0079 (3)	0.0021 (3)
I1	0.0498 (3)	0.0841 (4)	0.0397 (3)	0.0204 (2)	0.00761 (19)	−0.0118 (2)
I2	0.0731 (4)	0.0624 (3)	0.0512 (3)	0.0118 (2)	0.0009 (2)	0.0195 (2)
S1	0.0445 (8)	0.0693 (11)	0.0297 (7)	0.0026 (7)	0.0062 (6)	0.0014 (6)

Geometric parameters (Å, º) top

C1—N1	1.352 (9)	C10—H10B	0.9600
C1—C2	1.370 (10)	C10—H10A	0.9600
C1—H1	0.9300	C11—C12	1.372 (12)
C2—C3	1.383 (10)	C11—H11	0.9300
C2—H2	0.9300	C12—N2	1.341 (9)
C3—C5	1.388 (9)	C12—H12	0.9300
C3—C4	1.490 (9)	C13—S1	1.746 (12)
C4—H4C	0.9600	C13—H13A	0.9600
C4—H4B	0.9600	C13—H13B	0.9600
C4—H4A	0.9600	C13—H13C	0.9600
C5—C6	1.384 (8)	C14—S1	1.751 (10)
C5—H5	0.9300	C14—H14A	0.9600
C6—N1	1.334 (7)	C14—H14B	0.9600
C6—C7	1.488 (8)	C14—H14C	0.9600
C7—N2	1.341 (7)	Zn1—N1	2.135 (5)
C7—C8	1.387 (9)	Zn1—N2	2.167 (6)
C8—C9	1.368 (10)	O1—S1	1.513 (5)
C8—H8	0.9300	Zn1—O1	2.112 (5)
C9—C11	1.392 (11)	Zn1—I1	2.6199 (9)
C9—C10	1.498 (12)	Zn1—I2	2.6944 (9)
C10—H10C	0.9600

N1—C1—C2	123.3 (7)	C12—C11—H11	120.0
N1—C1—H1	118.3	C9—C11—H11	120.0
C2—C1—H1	118.3	N2—C12—C11	122.8 (7)
C1—C2—C3	119.7 (7)	N2—C12—H12	118.6
C1—C2—H2	120.2	C11—C12—H12	118.6
C3—C2—H2	120.2	S1—C13—H13A	109.5
C2—C3—C5	117.0 (6)	S1—C13—H13B	109.5
C2—C3—C4	122.0 (6)	H13A—C13—H13B	109.5
C5—C3—C4	121.1 (6)	S1—C13—H13C	109.5
C3—C4—H4C	109.5	H13A—C13—H13C	109.5
C3—C4—H4B	109.5	H13B—C13—H13C	109.5
H4C—C4—H4B	109.5	S1—C14—H14A	109.5
C3—C4—H4A	109.5	S1—C14—H14B	109.5
H4C—C4—H4A	109.5	H14A—C14—H14B	109.5
H4B—C4—H4A	109.5	S1—C14—H14C	109.5
C6—C5—C3	120.5 (6)	H14A—C14—H14C	109.5
C6—C5—H5	119.7	H14B—C14—H14C	109.5
C3—C5—H5	119.7	C6—N1—C1	117.4 (5)
N1—C6—C5	122.1 (6)	C6—N1—Zn1	117.2 (4)
N1—C6—C7	115.5 (5)	C1—N1—Zn1	125.2 (4)
C5—C6—C7	122.4 (5)	C12—N2—C7	117.9 (6)
N2—C7—C8	121.4 (6)	C12—N2—Zn1	126.3 (5)
N2—C7—C6	115.7 (5)	C7—N2—Zn1	115.7 (4)
C8—C7—C6	123.0 (5)	S1—O1—Zn1	122.0 (3)
C9—C8—C7	121.3 (6)	O1—Zn1—N1	83.89 (19)
C9—C8—H8	119.4	O1—Zn1—N2	150.80 (19)
C7—C8—H8	119.4	N1—Zn1—N2	75.84 (19)
C8—C9—C11	116.7 (7)	O1—Zn1—I1	99.96 (15)
C8—C9—C10	121.6 (7)	N1—Zn1—I1	107.68 (15)
C11—C9—C10	121.8 (7)	N2—Zn1—I1	106.06 (15)
C9—C10—H10C	109.5	O1—Zn1—I2	90.64 (15)
C9—C10—H10B	109.5	N1—Zn1—I2	142.63 (15)
H10C—C10—H10B	109.5	N2—Zn1—I2	92.86 (14)
C9—C10—H10A	109.5	I1—Zn1—I2	109.67 (3)
H10C—C10—H10A	109.5	O1—S1—C13	103.2 (5)
H10B—C10—H10A	109.5	O1—S1—C14	106.0 (4)
C12—C11—C9	119.9 (7)	C13—S1—C14	99.2 (9)

N1—C1—C2—C3	0.3 (13)	C8—C7—N2—C12	−1.0 (10)
C1—C2—C3—C5	0.9 (12)	C6—C7—N2—C12	178.8 (6)
C1—C2—C3—C4	−179.7 (8)	C8—C7—N2—Zn1	177.7 (5)
C2—C3—C5—C6	−1.9 (10)	C6—C7—N2—Zn1	−2.6 (7)
C4—C3—C5—C6	178.7 (7)	S1—O1—Zn1—N1	151.4 (4)
C3—C5—C6—N1	1.8 (10)	S1—O1—Zn1—N2	−162.7 (3)
C3—C5—C6—C7	−179.5 (6)	S1—O1—Zn1—I1	44.4 (4)
N1—C6—C7—N2	4.2 (8)	S1—O1—Zn1—I2	−65.7 (4)
C5—C6—C7—N2	−174.5 (6)	C6—N1—Zn1—O1	160.7 (5)
N1—C6—C7—C8	−176.1 (6)	C1—N1—Zn1—O1	−24.2 (6)
C5—C6—C7—C8	5.2 (10)	C6—N1—Zn1—N2	1.9 (4)
N2—C7—C8—C9	1.6 (11)	C1—N1—Zn1—N2	177.0 (6)
C6—C7—C8—C9	−178.1 (7)	C6—N1—Zn1—I1	−100.8 (4)
C7—C8—C9—C11	−0.6 (12)	C1—N1—Zn1—I1	74.3 (6)
C7—C8—C9—C10	−179.1 (8)	C6—N1—Zn1—I2	77.7 (5)
C8—C9—C11—C12	−0.8 (13)	C1—N1—Zn1—I2	−107.2 (6)
C10—C9—C11—C12	177.6 (9)	C12—N2—Zn1—O1	131.6 (6)
C9—C11—C12—N2	1.5 (14)	C7—N2—Zn1—O1	−46.9 (7)
C5—C6—N1—C1	−0.5 (9)	C12—N2—Zn1—N1	179.0 (7)
C7—C6—N1—C1	−179.3 (6)	C7—N2—Zn1—N1	0.5 (4)
C5—C6—N1—Zn1	174.9 (5)	C12—N2—Zn1—I1	−76.3 (6)
C7—C6—N1—Zn1	−3.8 (7)	C7—N2—Zn1—I1	105.2 (4)
C2—C1—N1—C6	−0.5 (11)	C12—N2—Zn1—I2	35.1 (6)
C2—C1—N1—Zn1	−175.6 (6)	C7—N2—Zn1—I2	−143.4 (4)
C11—C12—N2—C7	−0.5 (12)	Zn1—O1—S1—C13	−127.7 (9)
C11—C12—N2—Zn1	−179.0 (6)	Zn1—O1—S1—C14	128.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.93	2.41	2.938 (9)	116

Experimental details

Crystal data
Chemical formula	[ZnI₂(C₁₂H₁₂N₂)(C₂H₆OS)]
M_r	581.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.6173 (7), 15.5424 (11), 14.8976 (10)
β (°)	102.908 (6)
V (Å³)	1944.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.54
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.350, 0.636
No. of measured, independent and observed [I > 2σ(I)] reflections	21034, 5243, 4246
R_int	0.113
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.202, 1.20
No. of reflections	5243
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.11, −2.87

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Zn1—N1	2.135 (5)	Zn1—I1	2.6199 (9)
Zn1—N2	2.167 (6)	Zn1—I2	2.6944 (9)
Zn1—O1	2.112 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.93	2.41	2.938 (9)	116

Acknowledgements

The author is grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

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