cis-Dioxido[N′-(2-oxidobenzyl­idene)pyridinium-4-carbohydrazidato-κ3O,N′,O′]vanadium(V)

Shahverdizadeh, G.H.; Ng, S.W.; Tiekink, E.R.T.; Mirtamizdoust, B.

doi:10.1107/S1600536812003637

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m236

doi:10.1107/S1600536812003637

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cis-Dioxido[N′-(2-oxidobenzylidene)pyridinium-4-carbohydrazidato-κ³O,N′,O′]vanadium(V)

Gholam Hossein Shahverdizadeh,^a ‡ Seik Weng Ng,^b,^c Edward R. T. Tiekink ^b ^* and Babak Mirtamizdoust ^d

^aDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, and ^dDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, PO Box 5166616471, Tabriz, Iran
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 26 January 2012; accepted 27 January 2012; online 4 February 2012)

The title Schiff base complex, [V(C₁₃H₁₀N₃O₂)O₂], features a square-pyramidal coordination geometry defined by the O,N′,O′-donors of the tridentate Schiff base ligand and two oxide O atoms; one oxide O atom occupies the apical position. In the crystal, pyridinium–oxide N—H⋯O hydrogen bonds lead to zigzag supramolecular chains with a flattened topology along [101]. The investigated crystal was twinned by nonmerohedry; the minor component refined to 18.5 (5)%.

Related literature

For a related Schiff base vanadyl complex containing a protonated pyridyl residue, see: Yu et al. (2007 ). For the crystallization procedure, see: Harrowfield et al. (1996 ). For a related structure, see: Shahverdizadeh et al. (2012 ). For additional structural analysis, see: Spek (2009 ); Addison et al. (1984 ).

Experimental

Crystal data

[V(C₁₃H₁₀N₃O₂)O₂]
M_r = 323.18
Monoclinic, P 2₁ /n
a = 7.1215 (3) Å
b = 14.5243 (6) Å
c = 11.9233 (5) Å
β = 94.081 (3)°
V = 1230.16 (9) Å³
Z = 4
Cu Kα radiation
μ = 6.96 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.275, T_max = 0.275
2559 measured reflections
2559 independent reflections
2467 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.171
S = 1.26
2559 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
Selected bond lengths (Å)

V—O1	1.904 (3)
V—O2	2.006 (3)
V—O3	1.610 (4)
V—O4	1.654 (3)
V—N1	2.140 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O4ⁱ	0.88	1.75	2.610 (5)	164
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003637/bt5805sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003637/bt5805Isup2.hkl

checkCIF report

Comment top

In continuation of structural studies of vanadyl Schiff base complexes (Shahverdizadeh et al., 2012), the title complex, (I), was characterized.

The V atom in (I) is coordinated by the O,N,O-tridentate Schiff base ligand and two oxido-O atoms. The resulting NO₄ donor set is based on a square pyramid with oxido-O3 atom in the axial position. The coordination geometry is quantified by the calculation of τ = 0.05 which compares with τ = 0.0 for an ideal square pyramidal geometry and τ = 1.0 for an ideal trigonal bipyramid (Addison et al., 1984). The V═O3 bond length is significantly shorter than the V═O4 bond length, Table 1, an observation ascribed to the influence exerted by the trans-N1 atom and the participation of the oxido O4 atom in hydrogen bonding, Table 2. The pyridinium-NH···O(oxido) hydrogen bonding leads to a zigzag chain along [101] with a flattened topology.

The Schiff base ligand in (I) is present as a pyridinium cation. A precedent exists in the literature in a closely related V complex (Yu et al., 2007).

Related literature top

For a related Schiff base vanadyl complex containing a protonated pyridyl residue, see: Yu et al. (2007). For the crystallization procedure, see: Harrowfield et al. (1996). For a related structure, see: Shahverdizadeh et al. (2012). For additional structural analysis, see: Spek (2009); Addison et al. (1984).

Experimental top

A solution of salicylaldehyde (10 mmol) in EtOH (25 ml) was added drop-wise to the solution of 4-pyridinecarboxylic acid hydrazide (10 mmol) in EtOH (15 ml). The mixture was refluxed for 8 h. The yellow precipitate was removed by filtration and recrystallized from MeOH solution. The product (0.5 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and vanadium(IV) oxide acetylacetonate (0.5 mmol) in the other. Methanol was then added to fill both arms, the tube sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature. After 8 d, crystals had deposited in the arm held at ambient temperature. These filtered off, washed with acetone and ether, and air-dried. Yield: 72%. M.pt. 566 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	Fig. 2. A view of the zigzag supramolecular chain along [101] in (I). The N—H···O hydrogen bonds are shown as blue dashed lines.

cis-Dioxido[N'-(2-oxidobenzylidene)pyridinium-4-carbohydrazidato- κ³O,N',O']vanadium(V) top

Crystal data top

[V(C₁₃H₁₀N₃O₂)O₂]	F(000) = 656
M_r = 323.18	D_x = 1.745 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 5747 reflections
a = 7.1215 (3) Å	θ = 3.0–76.6°
b = 14.5243 (6) Å	µ = 6.96 mm⁻¹
c = 11.9233 (5) Å	T = 100 K
β = 94.081 (3)°	Polyhedron, brown
V = 1230.16 (9) Å³	0.25 × 0.25 × 0.25 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	2559 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2467 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.000
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.8°, θ_min = 4.8°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −18→18
T_min = 0.275, T_max = 0.275	l = −1→14
2559 measured 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.26	w = 1/[σ²(F_o²) + (0.0278P)² + 7.6276P] where P = (F_o² + 2F_c²)/3
2559 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 1.36 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

[V(C₁₃H₁₀N₃O₂)O₂]	V = 1230.16 (9) Å³
M_r = 323.18	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.1215 (3) Å	µ = 6.96 mm⁻¹
b = 14.5243 (6) Å	T = 100 K
c = 11.9233 (5) Å	0.25 × 0.25 × 0.25 mm
β = 94.081 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	2559 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2467 reflections with I > 2σ(I)
T_min = 0.275, T_max = 0.275	R_int = 0.000
2559 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.26	Δρ_max = 1.36 e Å⁻³
2559 reflections	Δρ_min = −0.84 e Å⁻³
191 parameters

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
V	0.65274 (12)	0.54174 (6)	0.30415 (6)	0.0148 (2)
O1	0.5622 (5)	0.6639 (2)	0.3213 (3)	0.0182 (7)
O2	0.6790 (5)	0.4125 (2)	0.3624 (3)	0.0153 (7)
O3	0.8525 (5)	0.5579 (3)	0.2519 (3)	0.0236 (8)
O4	0.4995 (5)	0.5080 (2)	0.2016 (3)	0.0203 (8)
N2	0.7647 (6)	0.4717 (3)	0.5387 (3)	0.0153 (8)
N1	0.7142 (6)	0.5531 (3)	0.4819 (3)	0.0131 (8)
N3	0.9037 (6)	0.1409 (3)	0.5891 (3)	0.0160 (8)
H1	0.9366	0.0860	0.6149	0.019*
C1	0.6069 (7)	0.7323 (3)	0.3920 (4)	0.0135 (9)
C2	0.5699 (7)	0.8232 (3)	0.3575 (4)	0.0162 (9)
H2	0.5206	0.8347	0.2827	0.019*
C3	0.6035 (7)	0.8964 (3)	0.4303 (4)	0.0186 (10)
H3	0.5744	0.9573	0.4055	0.022*
C4	0.6804 (7)	0.8817 (3)	0.5407 (4)	0.0180 (10)
H4	0.7032	0.9319	0.5907	0.022*
C5	0.7221 (7)	0.7929 (3)	0.5749 (4)	0.0146 (9)
H5	0.7756	0.7825	0.6491	0.018*
C6	0.6874 (6)	0.7174 (3)	0.5027 (4)	0.0135 (9)
C7	0.7303 (7)	0.6258 (3)	0.5432 (4)	0.0146 (9)
H7	0.7731	0.6187	0.6201	0.018*
C8	0.7437 (7)	0.4041 (3)	0.4673 (4)	0.0140 (9)
C9	0.7986 (6)	0.3110 (3)	0.5094 (4)	0.0135 (9)
C10	0.8734 (6)	0.2998 (3)	0.6209 (4)	0.0144 (9)
H10	0.8878	0.3512	0.6700	0.017*
C11	0.9251 (7)	0.2134 (3)	0.6575 (4)	0.0158 (9)
H11	0.9768	0.2051	0.7325	0.019*
C12	0.8337 (7)	0.1491 (3)	0.4826 (4)	0.0165 (10)
H12	0.8204	0.0959	0.4363	0.020*
C13	0.7805 (7)	0.2341 (3)	0.4394 (4)	0.0147 (9)
H13	0.7326	0.2402	0.3633	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V	0.0189 (4)	0.0164 (4)	0.0089 (4)	−0.0021 (3)	0.0006 (3)	−0.0011 (3)
O1	0.0264 (19)	0.0157 (16)	0.0122 (16)	0.0027 (14)	−0.0009 (14)	−0.0033 (13)
O2	0.0190 (17)	0.0179 (16)	0.0084 (14)	0.0027 (14)	−0.0028 (12)	0.0011 (12)
O3	0.028 (2)	0.0260 (19)	0.0183 (17)	−0.0065 (16)	0.0091 (15)	−0.0051 (14)
O4	0.028 (2)	0.0172 (16)	0.0151 (17)	−0.0034 (15)	−0.0057 (14)	0.0013 (13)
N2	0.018 (2)	0.0150 (19)	0.0125 (18)	−0.0010 (16)	−0.0001 (15)	0.0001 (15)
N1	0.0134 (19)	0.0172 (19)	0.0090 (17)	−0.0012 (15)	0.0024 (14)	0.0010 (14)
N3	0.016 (2)	0.0169 (19)	0.0153 (19)	0.0043 (16)	0.0030 (15)	0.0024 (15)
C1	0.011 (2)	0.018 (2)	0.012 (2)	0.0004 (17)	0.0019 (17)	−0.0018 (17)
C2	0.015 (2)	0.022 (2)	0.012 (2)	0.0002 (19)	0.0031 (17)	0.0031 (18)
C3	0.018 (2)	0.014 (2)	0.025 (3)	0.0009 (19)	0.007 (2)	0.0022 (19)
C4	0.014 (2)	0.018 (2)	0.022 (2)	−0.0007 (19)	0.0019 (19)	−0.0026 (19)
C5	0.015 (2)	0.018 (2)	0.011 (2)	0.0007 (18)	0.0040 (17)	−0.0035 (17)
C6	0.009 (2)	0.019 (2)	0.013 (2)	−0.0009 (17)	0.0049 (17)	−0.0017 (17)
C7	0.015 (2)	0.021 (2)	0.008 (2)	−0.0014 (19)	0.0021 (17)	−0.0007 (17)
C8	0.013 (2)	0.018 (2)	0.012 (2)	−0.0003 (18)	0.0014 (17)	0.0021 (17)
C9	0.007 (2)	0.019 (2)	0.015 (2)	0.0000 (17)	0.0023 (16)	0.0018 (18)
C10	0.012 (2)	0.018 (2)	0.012 (2)	−0.0026 (18)	−0.0020 (17)	0.0000 (17)
C11	0.013 (2)	0.021 (2)	0.013 (2)	0.0009 (18)	0.0011 (17)	0.0012 (18)
C12	0.019 (2)	0.020 (2)	0.011 (2)	0.0035 (19)	0.0031 (18)	−0.0005 (18)
C13	0.016 (2)	0.019 (2)	0.009 (2)	−0.0001 (18)	0.0025 (17)	0.0017 (17)

Geometric parameters (Å, º) top

V—O1	1.904 (3)	C3—C4	1.405 (7)
V—O2	2.006 (3)	C3—H3	0.9500
V—O3	1.610 (4)	C4—C5	1.379 (7)
V—O4	1.654 (3)	C4—H4	0.9500
V—N1	2.140 (4)	C5—C6	1.405 (6)
O1—C1	1.327 (6)	C5—H5	0.9500
O2—C8	1.307 (5)	C6—C7	1.441 (7)
N2—C8	1.301 (6)	C7—H7	0.9500
N2—N1	1.396 (5)	C8—C9	1.485 (6)
N1—C7	1.285 (6)	C9—C13	1.394 (7)
N3—C11	1.335 (6)	C9—C10	1.406 (6)
N3—C12	1.336 (6)	C10—C11	1.370 (7)
N3—H1	0.8800	C10—H10	0.9500
C1—C2	1.402 (7)	C11—H11	0.9500
C1—C6	1.418 (6)	C12—C13	1.382 (7)
C2—C3	1.383 (7)	C12—H12	0.9500
C2—H2	0.9500	C13—H13	0.9500

O3—V—O4	108.16 (19)	C5—C4—H4	120.6
O3—V—O1	102.77 (18)	C3—C4—H4	120.6
O4—V—O1	98.34 (16)	C4—C5—C6	121.5 (4)
O3—V—O2	101.95 (17)	C4—C5—H5	119.2
O4—V—O2	91.08 (15)	C6—C5—H5	119.2
O1—V—O2	149.21 (14)	C5—C6—C1	119.6 (4)
O3—V—N1	104.35 (17)	C5—C6—C7	119.4 (4)
O4—V—N1	146.37 (17)	C1—C6—C7	121.0 (4)
O1—V—N1	82.48 (15)	N1—C7—C6	124.0 (4)
O2—V—N1	73.82 (14)	N1—C7—H7	118.0
C1—O1—V	134.3 (3)	C6—C7—H7	118.0
C8—O2—V	115.9 (3)	N2—C8—O2	124.9 (4)
C8—N2—N1	108.0 (4)	N2—C8—C9	116.8 (4)
C7—N1—N2	114.2 (4)	O2—C8—C9	118.3 (4)
C7—N1—V	129.1 (3)	C13—C9—C10	119.1 (4)
N2—N1—V	116.3 (3)	C13—C9—C8	121.0 (4)
C11—N3—C12	122.0 (4)	C10—C9—C8	119.9 (4)
C11—N3—H1	119.0	C11—C10—C9	118.8 (4)
C12—N3—H1	119.0	C11—C10—H10	120.6
O1—C1—C2	119.1 (4)	C9—C10—H10	120.6
O1—C1—C6	122.7 (4)	N3—C11—C10	120.8 (4)
C2—C1—C6	118.2 (4)	N3—C11—H11	119.6
C3—C2—C1	121.3 (4)	C10—C11—H11	119.6
C3—C2—H2	119.3	N3—C12—C13	120.5 (4)
C1—C2—H2	119.3	N3—C12—H12	119.7
C2—C3—C4	120.6 (5)	C13—C12—H12	119.7
C2—C3—H3	119.7	C12—C13—C9	118.8 (4)
C4—C3—H3	119.7	C12—C13—H13	120.6
C5—C4—C3	118.8 (4)	C9—C13—H13	120.6

O3—V—O1—C1	−73.7 (4)	C4—C5—C6—C7	−178.8 (5)
O4—V—O1—C1	175.5 (4)	O1—C1—C6—C5	−176.7 (4)
O2—V—O1—C1	69.0 (6)	C2—C1—C6—C5	1.9 (7)
N1—V—O1—C1	29.4 (4)	O1—C1—C6—C7	1.9 (7)
O3—V—O2—C8	92.1 (3)	C2—C1—C6—C7	−179.6 (4)
O4—V—O2—C8	−159.1 (3)	N2—N1—C7—C6	179.6 (4)
O1—V—O2—C8	−50.7 (5)	V—N1—C7—C6	7.4 (7)
N1—V—O2—C8	−9.6 (3)	C5—C6—C7—N1	−175.7 (5)
C8—N2—N1—C7	−179.4 (4)	C1—C6—C7—N1	5.7 (7)
C8—N2—N1—V	−6.2 (5)	N1—N2—C8—O2	−2.6 (6)
O3—V—N1—C7	82.3 (4)	N1—N2—C8—C9	177.3 (4)
O4—V—N1—C7	−112.8 (5)	V—O2—C8—N2	10.6 (6)
O1—V—N1—C7	−19.1 (4)	V—O2—C8—C9	−169.3 (3)
O2—V—N1—C7	−179.2 (4)	N2—C8—C9—C13	179.7 (4)
O3—V—N1—N2	−89.8 (3)	O2—C8—C9—C13	−0.4 (7)
O4—V—N1—N2	75.1 (4)	N2—C8—C9—C10	−1.5 (7)
O1—V—N1—N2	168.9 (3)	O2—C8—C9—C10	178.3 (4)
O2—V—N1—N2	8.7 (3)	C13—C9—C10—C11	−0.5 (7)
V—O1—C1—C2	154.5 (4)	C8—C9—C10—C11	−179.2 (4)
V—O1—C1—C6	−27.0 (7)	C12—N3—C11—C10	0.8 (7)
O1—C1—C2—C3	176.1 (4)	C9—C10—C11—N3	−0.5 (7)
C6—C1—C2—C3	−2.5 (7)	C11—N3—C12—C13	0.0 (7)
C1—C2—C3—C4	1.5 (7)	N3—C12—C13—C9	−1.0 (7)
C2—C3—C4—C5	0.2 (7)	C10—C9—C13—C12	1.2 (7)
C3—C4—C5—C6	−0.8 (7)	C8—C9—C13—C12	179.9 (4)
C4—C5—C6—C1	−0.3 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O4ⁱ	0.88	1.75	2.610 (5)	164

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[V(C₁₃H₁₀N₃O₂)O₂]
M_r	323.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.1215 (3), 14.5243 (6), 11.9233 (5)
β (°)	94.081 (3)
V (Å³)	1230.16 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	6.96
Crystal size (mm)	0.25 × 0.25 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.275, 0.275
No. of measured, independent and observed [I > 2σ(I)] reflections	2559, 2559, 2467
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.171, 1.26
No. of reflections	2559
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.36, −0.84

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

V—O1	1.904 (3)	V—O4	1.654 (3)
V—O2	2.006 (3)	V—N1	2.140 (4)
V—O3	1.610 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O4ⁱ	0.88	1.75	2.610 (5)	164

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Footnotes

‡Additional correspondence author, e-mail: shahverdizadeh@iaut.ac.ir.

Acknowledgements

The authors gratefully acknowledge support of this study by Tabriz Azad University, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harrowfield, J. M., Miyamae, H., Skelton, B. W., Soudi, A. A. & White, A. H. (1996). Aust. J. Chem. 49, 1165–1169. CSD CrossRef Web of Science Google Scholar
Shahverdizadeh, G. H., Ng, S. W., Tiekink, E. R. T. & Mirtamizdoust, B. (2012). Acta Cryst. E68, m221-m222. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, Q., Li, C.-Y., Bian, H.-D., Liang, H., Song, H.-S. & Wang, H.-G. (2007). Chin. J. Struct. Chem. 26, 37–40. CAS Google Scholar

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