Dibromido(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)zinc(II)

Alizadeh, R.; Mohammadi Eshlaghi, P.; Amani, V.

doi:10.1107/S1600536810028692

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m996

https://doi.org/10.1107/S1600536810028692

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Dibromido(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)zinc(II)

Robabeh Alizadeh,^a ^* Parisa Mohammadi Eshlaghi ^a and Vahid Amani ^b

^aSchool of Chemistry, Damghan University, Damghan, Iran, and ^bIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: robabeh_alizadeh@yahoo.com

(Received 17 July 2010; accepted 18 July 2010; online 24 July 2010)

The asymmetric unit of the title compound, [ZnBr₂(C₁₂H₁₂N₂)], contains two half-molecules; both are completed by crystallographic twofold axes running through the Zn^II atoms which are coordinated by an N,N′-bidentate 4,4′-dimethyl-2,2′-bipyridine ligand and two Br⁻ ions, resulting in distorted ZnN₂Br₂ tetrahedral coordination geometries. In the crystal, C—H⋯Br interactions link the molecules.

Related literature

For related structures, see: Ahmadi et al. (2008 ); 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

[ZnBr₂(C₁₂H₁₂N₂)]
M_r = 409.43
Monoclinic, P 2/c
a = 13.801 (3) Å
b = 8.2454 (16) Å
c = 13.716 (3) Å
β = 117.47 (3)°
V = 1384.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 7.52 mm⁻¹
T = 120 K
0.30 × 0.22 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.157, T_max = 0.479
8352 measured reflections
3560 independent reflections
2963 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.099
S = 1.07
3560 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −1.04 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N1	2.053 (3)
Zn2—N2	2.050 (3)
Zn1—Br1	2.3428 (6)
Zn2—Br2	2.3356 (9)

N1—Zn1—N1ⁱ	80.61 (17)
N2—Zn2—N2ⁱⁱ	81.15 (17)
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Br1ⁱⁱⁱ	0.96	2.89	3.772 (5)	152
Symmetry code: (iii) x, y-1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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 datablocks I, global. DOI: https://doi.org/10.1107/S1600536810028692/hb5556sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028692/hb5556Isup2.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), platin (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), iridium (Yoshikawa et al., 2003) and cadmium (Kalateh et al., 2010). Here, we report the synthesis and structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), contains two half-molecule. The Zn^II atom is for-coordinated in distorted tetragonal configurations by two N atoms from one 4,4'-dimethyl-2,2'-bipyridine and two Br atoms. The Zn—Br and Zn—N bond lengths and angles are collected in Table 1.

In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2) may stabilize the structure (Fig. 2).

Related literature top

For related structures, see: Ahmadi et al. (2008); 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

A solution of 4,4'-dimethyl-2,2'-bipyridine (0.20 g, 1.10 mmol) in methanol (10 ml) was added to a solution of ZnBr₂ (0.25 g, 1.10 mmol) in methanol (5 ml) at room temperature. Colourless prisms of (I) were obtained by methanol diffusion to a colorless solution in DMSO. Suitable crystals were isolated after one week (yield; 0.35 g, 77.7%).

Structure description top

In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2) may stabilize the structure (Fig. 2).

For related structures, see: Ahmadi et al. (2008); 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).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (I) with displacement ellipsoids drawn at the 50% probability level. Atoms with suffix a are generated by (1–x, y, 1/2–z); those with suffix b are generated by (–x, y, 1/2–z).
	Fig. 2. Unit-cell packing diagram for (I). Hydrogen bonds are shown as dashed lines.

Dibromido(4,4'-dimethyl-2,2'-bipyridine-κ²N,N')zinc(II) top

Crystal data top

[ZnBr₂(C₁₂H₁₂N₂)]	F(000) = 792
M_r = 409.43	D_x = 1.964 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 984 reflections
a = 13.801 (3) Å	θ = 2.5–29.2°
b = 8.2454 (16) Å	µ = 7.52 mm⁻¹
c = 13.716 (3) Å	T = 120 K
β = 117.47 (3)°	Prism, colorless
V = 1384.9 (6) Å³	0.30 × 0.22 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3560 independent reflections
Radiation source: fine-focus sealed tube	2963 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
phi and ω scans	θ_max = 29.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→18
T_min = 0.157, T_max = 0.479	k = −11→11
8352 measured reflections	l = −18→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0449P)² + 2.823P] where P = (F_o² + 2F_c²)/3
3560 reflections	(Δ/σ)_max = 0.001
156 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −1.04 e Å⁻³

Crystal data top

[ZnBr₂(C₁₂H₁₂N₂)]	V = 1384.9 (6) Å³
M_r = 409.43	Z = 4
Monoclinic, P2/c	Mo Kα radiation
a = 13.801 (3) Å	µ = 7.52 mm⁻¹
b = 8.2454 (16) Å	T = 120 K
c = 13.716 (3) Å	0.30 × 0.22 × 0.10 mm
β = 117.47 (3)°

Data collection top

Bruker SMART CCD diffractometer	3560 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2963 reflections with I > 2σ(I)
T_min = 0.157, T_max = 0.479	R_int = 0.050
8352 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	Δρ_max = 0.62 e Å⁻³
3560 reflections	Δρ_min = −1.04 e Å⁻³
156 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
C1	0.3828 (3)	0.7308 (4)	0.0326 (3)	0.0225 (7)
H1	0.3650	0.8327	0.0001	0.027*
C2	0.3490 (3)	0.5946 (5)	−0.0343 (3)	0.0251 (8)
H2	0.3082	0.6056	−0.1101	0.030*
C3	0.3767 (3)	0.4417 (4)	0.0131 (3)	0.0234 (7)
C4	0.3428 (4)	0.2903 (5)	−0.0556 (4)	0.0313 (9)
H4A	0.2979	0.2252	−0.0345	0.038*
H4B	0.4065	0.2299	−0.0444	0.038*
H4C	0.3022	0.3191	−0.1318	0.038*
C5	0.4366 (3)	0.4324 (4)	0.1268 (3)	0.0220 (7)
H5	0.4562	0.3319	0.1611	0.026*
C6	0.4671 (3)	0.5733 (4)	0.1892 (3)	0.0185 (7)
C7	0.1273 (3)	0.7510 (4)	0.1512 (3)	0.0231 (7)
H7	0.1512	0.8521	0.1411	0.028*
C8	0.1556 (3)	0.6153 (5)	0.1110 (3)	0.0236 (7)
H8	0.1977	0.6260	0.0746	0.028*
C9	0.1209 (3)	0.4623 (4)	0.1250 (3)	0.0208 (7)
C10	0.1447 (4)	0.3130 (5)	0.0775 (4)	0.0287 (8)
H10C	0.1371	0.3370	0.0058	0.034*
H10B	0.0943	0.2289	0.0718	0.034*
H10A	0.2179	0.2774	0.1244	0.034*
C11	0.0594 (3)	0.4535 (4)	0.1817 (3)	0.0218 (7)
H11	0.0357	0.3534	0.1938	0.026*
C12	0.0334 (3)	0.5942 (4)	0.2202 (3)	0.0181 (7)
N1	0.4399 (3)	0.7211 (3)	0.1415 (3)	0.0186 (6)
N2	0.0668 (3)	0.7419 (3)	0.2042 (3)	0.0186 (6)
Zn1	0.5000	0.91089 (6)	0.2500	0.02024 (14)
Zn2	0.0000	0.93068 (6)	0.2500	0.01997 (14)
Br1	0.37461 (4)	1.05907 (4)	0.28513 (4)	0.02607 (11)
Br2	0.12396 (4)	1.07654 (4)	0.40271 (4)	0.02828 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0274 (19)	0.0185 (15)	0.0221 (19)	0.0011 (14)	0.0119 (16)	0.0019 (13)
C2	0.0263 (19)	0.0284 (18)	0.0186 (18)	−0.0019 (15)	0.0085 (15)	−0.0024 (14)
C3	0.0261 (19)	0.0232 (16)	0.0232 (19)	−0.0021 (14)	0.0134 (16)	−0.0059 (14)
C4	0.035 (2)	0.0265 (18)	0.026 (2)	−0.0044 (17)	0.0089 (18)	−0.0115 (16)
C5	0.0271 (19)	0.0141 (14)	0.0249 (19)	−0.0016 (13)	0.0121 (16)	−0.0035 (12)
C6	0.0262 (18)	0.0125 (13)	0.0187 (18)	−0.0021 (12)	0.0118 (15)	−0.0013 (12)
C7	0.0268 (19)	0.0184 (15)	0.025 (2)	−0.0015 (14)	0.0127 (16)	0.0010 (13)
C8	0.028 (2)	0.0240 (16)	0.025 (2)	0.0003 (15)	0.0171 (17)	0.0010 (14)
C9	0.0227 (18)	0.0196 (15)	0.0191 (18)	0.0039 (13)	0.0087 (15)	−0.0007 (13)
C10	0.033 (2)	0.0238 (17)	0.033 (2)	0.0066 (16)	0.0183 (19)	−0.0023 (15)
C11	0.0289 (19)	0.0138 (14)	0.0249 (19)	0.0006 (13)	0.0142 (16)	−0.0001 (12)
C12	0.0227 (17)	0.0133 (14)	0.0192 (18)	0.0012 (12)	0.0104 (15)	0.0003 (11)
N1	0.0222 (15)	0.0147 (12)	0.0177 (15)	−0.0004 (11)	0.0082 (12)	−0.0013 (10)
N2	0.0253 (16)	0.0129 (12)	0.0175 (15)	−0.0004 (11)	0.0097 (13)	0.0004 (10)
Zn1	0.0277 (3)	0.0107 (2)	0.0231 (3)	0.000	0.0123 (3)	0.000
Zn2	0.0274 (3)	0.0106 (2)	0.0212 (3)	0.000	0.0106 (3)	0.000
Br1	0.0329 (2)	0.01709 (16)	0.0322 (2)	0.00397 (14)	0.01838 (17)	0.00109 (14)
Br2	0.0317 (2)	0.01954 (17)	0.0281 (2)	−0.00180 (14)	0.00900 (17)	−0.00723 (14)

Geometric parameters (Å, º) top

C1—N1	1.332 (5)	C8—H8	0.9300
C1—C2	1.388 (5)	C9—C11	1.394 (5)
C1—H1	0.9300	C9—C10	1.498 (5)
C2—C3	1.388 (5)	C10—H10C	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C5	1.390 (6)	C10—H10A	0.9600
C3—C4	1.503 (5)	C11—C12	1.389 (5)
C4—H4A	0.9600	C11—H11	0.9300
C4—H4B	0.9600	C12—N2	1.355 (4)
C4—H4C	0.9600	C12—C12ⁱⁱ	1.488 (7)
C5—C6	1.387 (5)	Zn1—N1	2.053 (3)
C5—H5	0.9300	Zn2—N2	2.050 (3)
C6—N1	1.351 (4)	Zn1—N1ⁱ	2.053 (3)
C6—C6ⁱ	1.487 (8)	Zn1—Br1ⁱ	2.3428 (6)
C7—N2	1.339 (5)	Zn1—Br1	2.3428 (6)
C7—C8	1.380 (5)	Zn2—N2ⁱⁱ	2.050 (3)
C7—H7	0.9300	Zn2—Br2	2.3356 (9)
C8—C9	1.393 (5)	Zn2—Br2ⁱⁱ	2.3356 (9)

N1—C1—C2	122.5 (3)	C9—C10—H10C	109.5
N1—C1—H1	118.7	C9—C10—H10B	109.5
C2—C1—H1	118.7	H10C—C10—H10B	109.5
C1—C2—C3	119.3 (4)	C9—C10—H10A	109.5
C1—C2—H2	120.4	H10C—C10—H10A	109.5
C3—C2—H2	120.4	H10B—C10—H10A	109.5
C2—C3—C5	117.9 (3)	C12—C11—C9	120.0 (3)
C2—C3—C4	121.4 (4)	C12—C11—H11	120.0
C5—C3—C4	120.6 (4)	C9—C11—H11	120.0
C3—C4—H4A	109.5	N2—C12—C11	121.5 (3)
C3—C4—H4B	109.5	N2—C12—C12ⁱⁱ	115.6 (2)
H4A—C4—H4B	109.5	C11—C12—C12ⁱⁱ	122.9 (2)
C3—C4—H4C	109.5	C1—N1—C6	119.0 (3)
H4A—C4—H4C	109.5	C1—N1—Zn1	126.8 (2)
H4B—C4—H4C	109.5	C6—N1—Zn1	114.1 (2)
C6—C5—C3	120.0 (3)	C7—N2—C12	118.8 (3)
C6—C5—H5	120.0	C7—N2—Zn2	127.2 (2)
C3—C5—H5	120.0	C12—N2—Zn2	113.5 (2)
N1—C6—C5	121.3 (4)	N1—Zn1—N1ⁱ	80.61 (17)
N1—C6—C6ⁱ	115.6 (2)	N1—Zn1—Br1ⁱ	109.77 (9)
C5—C6—C6ⁱ	123.1 (2)	N1ⁱ—Zn1—Br1ⁱ	117.20 (9)
N2—C7—C8	122.2 (3)	N1—Zn1—Br1	117.20 (9)
N2—C7—H7	118.9	N1ⁱ—Zn1—Br1	109.77 (9)
C8—C7—H7	118.9	Br1ⁱ—Zn1—Br1	117.13 (3)
C7—C8—C9	120.1 (3)	N2—Zn2—N2ⁱⁱ	81.15 (17)
C7—C8—H8	119.9	N2—Zn2—Br2	114.76 (9)
C9—C8—H8	119.9	N2ⁱⁱ—Zn2—Br2	111.31 (9)
C8—C9—C11	117.4 (3)	N2—Zn2—Br2ⁱⁱ	111.31 (9)
C8—C9—C10	121.8 (3)	N2ⁱⁱ—Zn2—Br2ⁱⁱ	114.76 (9)
C11—C9—C10	120.8 (3)	Br2—Zn2—Br2ⁱⁱ	118.01 (4)

N1—C1—C2—C3	−1.1 (6)	C6ⁱ—C6—N1—Zn1	1.4 (5)
C1—C2—C3—C5	0.8 (6)	C8—C7—N2—C12	0.9 (6)
C1—C2—C3—C4	−179.6 (4)	C8—C7—N2—Zn2	−170.8 (3)
C2—C3—C5—C6	−0.2 (6)	C11—C12—N2—C7	−0.8 (6)
C4—C3—C5—C6	−179.9 (4)	C12ⁱⁱ—C12—N2—C7	179.9 (4)
C3—C5—C6—N1	−0.2 (6)	C11—C12—N2—Zn2	172.0 (3)
C3—C5—C6—C6ⁱ	−178.8 (4)	C12ⁱⁱ—C12—N2—Zn2	−7.3 (5)
N2—C7—C8—C9	0.0 (6)	C1—N1—Zn1—N1ⁱ	−177.6 (4)
C7—C8—C9—C11	−1.0 (6)	C6—N1—Zn1—N1ⁱ	−0.5 (2)
C7—C8—C9—C10	176.7 (4)	C1—N1—Zn1—Br1ⁱ	−62.0 (3)
C8—C9—C11—C12	1.0 (6)	C6—N1—Zn1—Br1ⁱ	115.1 (3)
C10—C9—C11—C12	−176.7 (4)	C1—N1—Zn1—Br1	74.9 (3)
C9—C11—C12—N2	−0.2 (6)	C6—N1—Zn1—Br1	−108.0 (3)
C9—C11—C12—C12ⁱⁱ	179.1 (4)	C7—N2—Zn2—N2ⁱⁱ	174.8 (4)
C2—C1—N1—C6	0.7 (6)	C12—N2—Zn2—N2ⁱⁱ	2.71 (19)
C2—C1—N1—Zn1	177.7 (3)	C7—N2—Zn2—Br2	−75.8 (3)
C5—C6—N1—C1	−0.1 (6)	C12—N2—Zn2—Br2	112.2 (3)
C6ⁱ—C6—N1—C1	178.7 (4)	C7—N2—Zn2—Br2ⁱⁱ	61.5 (3)
C5—C6—N1—Zn1	−177.4 (3)	C12—N2—Zn2—Br2ⁱⁱ	−110.5 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Br1ⁱⁱⁱ	0.96	2.89	3.772 (5)	152

Symmetry code: (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[ZnBr₂(C₁₂H₁₂N₂)]
M_r	409.43
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	120
a, b, c (Å)	13.801 (3), 8.2454 (16), 13.716 (3)
β (°)	117.47 (3)
V (Å³)	1384.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.52
Crystal size (mm)	0.30 × 0.22 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.157, 0.479
No. of measured, independent and observed [I > 2σ(I)] reflections	8352, 3560, 2963
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.099, 1.07
No. of reflections	3560
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −1.04

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Zn1—N1	2.053 (3)	Zn1—Br1	2.3428 (6)
Zn2—N2	2.050 (3)	Zn2—Br2	2.3356 (9)

N1—Zn1—N1ⁱ	80.61 (17)	N2—Zn2—N2ⁱⁱ	81.15 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Br1ⁱⁱⁱ	0.96	2.89	3.772 (5)	152

Symmetry code: (iii) x, y−1, z.

Acknowledgements

We are grateful to Damghan University for financial support.

References

Ahmadi, R., Kalateh, K., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1306–m1307. Web of Science CSD CrossRef IUCr Journals Google Scholar
Amani, V., Safari, N., Notash, B. & Khavasi, H. R. (2009). J. Coord. Chem. 62, 1939–1950. Web of Science CSD CrossRef CAS Google Scholar
Bellusci, A., Crispini, A., Pucci, D., Szerb, E. I. & Ghedini, M. (2008). Cryst. Growth Des. 8, 3114–3122. Web of Science CSD CrossRef CAS Google Scholar
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hojjat Kashani, L., Amani, V., Yousefi, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m905–m906. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kalateh, K., Ahmadi, R. & Amani, V. (2010). Acta Cryst. E66, m512. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kalateh, K., Ebadi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1397–m1398. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sakamoto, J., Yoshikawa, N., Takashima, H., Tsukahara, K., Kanehisa, N., Kai, Y. & Matsumura, K. (2004). Acta Cryst. E60, m352–m353. 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
Sofetis, A., Raptopoulou, C. P., Terzis, A. & Zafiropoulos, T. F. (2006). Inorg. Chim. Acta, 359, 3389–3395. Web of Science CSD CrossRef CAS Google Scholar
Willett, R. D., Pon, G. & Nagy, C. (2001). Inorg. Chem. 40, 4342–4352. Web of Science CSD CrossRef PubMed CAS Google Scholar
Yoshikawa, N., Sakamoto, J., Kanehisa, N., Kai, Y. & Matsumura-Inoue, T. (2003). Acta Cryst. E59, m155–m156. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yousefi, M., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1259. Web of Science CSD CrossRef IUCr Journals Google Scholar