Dichlorido(di-2-pyridylamine)mercury(II)

Yousefi, M.; Allahgholi Ghasri, M.R.; Heidari, A.; Amani, V.

doi:10.1107/S1600536808040294

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages m9-m10

doi:10.1107/S1600536808040294

Open

access

Dichlorido(di-2-pyridylamine)mercury(II)

Mohammad Yousefi,^a Mohammad Reza Allahgholi Ghasri,^a Amene Heidari ^b and Vahid Amani ^a ^*

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, and ^bDepartment of Chemistry, University of Zabol, Iran
^*Correspondence e-mail: v_amani2002@yahoo.com

(Received 28 November 2008; accepted 30 November 2008; online 6 December 2008)

In the molecule of the title compound, [HgCl₂(C₁₀H₉N₃)], the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from the chelating di-2-pyridylamine ligand and by two Cl atoms. In the crystal structure, intermolecular N—H⋯Cl hydrogen bonds link the molecules into centrosymmetric dimers. There is a π–π contact between the pyridine rings [centroid–centroid distance = 3.896 (5) Å].

Related literature

For related literature, see: Ahmadi et al. (2008 ); Kalateh, Ebadi et al. (2008 ); Kalateh, Norouzi et al. (2008 ); Khavasi et al. (2008 ); Tadayon Pour et al. (2008 ); Yousefi, Rashidi Vahid et al. (2008 ); Yousefi, Tadayon Pour et al. (2008 ). For related structures, see: Chen et al. (2006 ); Liu et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[HgCl₂(C₁₀H₉N₃)]
M_r = 442.69
Triclinic, $[P \overline 1]$
a = 8.0268 (12) Å
b = 8.6127 (11) Å
c = 9.6118 (14) Å
α = 110.606 (11)°
β = 98.958 (12)°
γ = 96.862 (11)°
V = 603.38 (15) Å³
Z = 2
Mo Kα radiation
μ = 13.17 mm⁻¹
T = 298 (2) K
0.24 × 0.21 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi scan (SADABS; Sheldrick, 1998 ) T_min = 0.061, T_max = 0.142
7105 measured reflections
3214 independent reflections
2806 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.126
S = 1.05
3214 reflections
150 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.43 e Å⁻³
Δρ_min = −2.08 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cl1—Hg1	2.3875 (19)
Cl2—Hg1	2.4579 (19)
N1—Hg1	2.369 (6)
N3—Hg1	2.290 (6)

N1—Hg1—Cl1	112.30 (15)
N1—Hg1—Cl2	94.92 (15)
N3—Hg1—Cl1	112.21 (15)
N3—Hg1—Cl2	123.92 (14)
N3—Hg1—N1	82.4 (2)
Cl1—Hg1—Cl2	120.14 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯Cl2ⁱ	0.95 (16)	2.41 (16)	3.345 (6)	169 (13)
Symmetry code: (i) -x, -y+1, -z+1.

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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040294/hk2588sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040294/hk2588Isup2.hkl

checkCIF report

Comment top

Recently, we reported the synthes and crystal structures of [Hg(NH(py)₂)Br₂], (II), (Kalateh, Norouzi et al., 2008), [Hg(4,4'-dmbpy)I₂], (III), (Yousefi, Tadayon Pour et al., 2008), [Hg(5,5'-dmbpy)I₂], (IV), (Tadayon Pour et al., 2008), [Hg(dmphen)I₂], (V), (Yousefi, Rashidi Vahid et al., 2008), {[HgCl(dm4bt)]₂(µ-Cl)₂}, (VI), (Khavasi et al., 2008), [Hg(6-mbpy)Cl₂], (VII), (Ahmadi et al., 2008) and [{HgBr(4,4'-dmbpy)}₂(µ-Br)₂], (VIII), (Kalateh, Ebadi et al., 2008) [where NH(py)₂ is di-2-pyridylamine, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2'-bipyridine, dmphen is 4,7-diphenyl- 1,10-phenanthroline and dm4bt is 2,2'-dimethyl-4,4'-bithiazole].

There are several Hg^II complexes, with formula, [Hg(N—N)Cl₂], such as [Hg(bipy)Cl₂], (IX), and [Hg(bipy)Cl₂][HgCl₂], (X), (Chen et al., 2006) and [Hg(dpdmbip) Cl₂].CH₂Cl₂, (XI), (Liu et al., 2004) [where bipy is 2,2'-bipyridine and dpdmbip is 4,4'-diphenyl-6,6'-dimethyl-2,2'-bipyrimidine] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound, (Fig. 1), the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from di-2-pyridylamine and two Cl atoms. The Hg-Cl and Hg-N bond lengths (Allen et al., 1987) and angles (Table 1) are within normal ranges.

In the crystal structure, intermolecular N-H···Cl hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers, in which they may be effective in the stabilization of the crystal structure (Fig. 2). The π-π contact between the pyridine rings, Cg2···Cg3ⁱ [symmetry code: (i) -x, 1 - y, 1 - z, where Cg2 and Cg3 are centroids of the rings A (N1/C1-C5) and B (N3/C6-C10), respectively] may further stabilize the structure, with centroid-centroid distance of 3.896 (5)%A.

Related literature top

For related literature, see: Ahmadi et al. (2008); Kalateh, Ebadi et al. (2008); Kalateh, Norouzi et al. (2008); Khavasi et al. (2008); Tadayon Pour et al. (2008); Yousefi, Rashidi Vahid et al. (2008); Yousefi, Tadayon Pour et al. (2008). For related structures, see: Chen et al. (2006); Liu et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, (I), a solution of di-2-pyridylamine (0.25 g, 1.43 mmol) in methanol (20 ml) was added to a solution of HgCl₂ (0.39 g, 1.43 mmol) in acetonitrile (20 ml) and the resulting colorless solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, colorless block crystals of the title compound were isolated (yield; 0.47 g, 74.3%).

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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Dichlorido(di-2-pyridylamine)mercury(II) top

Crystal data top

[HgCl₂(C₁₀H₉N₃)]	Z = 2
M_r = 442.69	F(000) = 408
Triclinic, P1	D_x = 2.437 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0268 (12) Å	Cell parameters from 1652 reflections
b = 8.6127 (11) Å	θ = 2.6–29.2°
c = 9.6118 (14) Å	µ = 13.17 mm⁻¹
α = 110.606 (11)°	T = 298 K
β = 98.958 (12)°	Block, colorless
γ = 96.862 (11)°	0.24 × 0.21 × 0.15 mm
V = 603.38 (15) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3214 independent reflections
Radiation source: fine-focus sealed tube	2806 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ϕ and ω scans	θ_max = 29.2°, θ_min = 2.6°
Absorption correction: multi scan (SADABS; Sheldrick, 1998)	h = −10→10
T_min = 0.061, T_max = 0.142	k = −11→11
7105 measured reflections	l = −13→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.075P)² + 0.8992P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.026
3214 reflections	Δρ_max = 2.43 e Å⁻³
150 parameters	Δρ_min = −2.08 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (3)

Crystal data top

[HgCl₂(C₁₀H₉N₃)]	γ = 96.862 (11)°
M_r = 442.69	V = 603.38 (15) Å³
Triclinic, P1	Z = 2
a = 8.0268 (12) Å	Mo Kα radiation
b = 8.6127 (11) Å	µ = 13.17 mm⁻¹
c = 9.6118 (14) Å	T = 298 K
α = 110.606 (11)°	0.24 × 0.21 × 0.15 mm
β = 98.958 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3214 independent reflections
Absorption correction: multi scan (SADABS; Sheldrick, 1998)	2806 reflections with I > 2σ(I)
T_min = 0.061, T_max = 0.142	R_int = 0.069
7105 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 2.43 e Å⁻³
3214 reflections	Δρ_min = −2.08 e Å⁻³
150 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
Hg1	0.21151 (4)	0.24646 (4)	0.63832 (4)	0.06055 (18)
Cl1	0.4456 (3)	0.1830 (3)	0.7818 (3)	0.0683 (5)
Cl2	−0.0856 (2)	0.1450 (2)	0.6448 (2)	0.0553 (4)
N1	0.1944 (8)	0.5364 (8)	0.7382 (7)	0.0497 (12)
N2	0.2047 (8)	0.5833 (7)	0.5110 (6)	0.0459 (11)
N3	0.2876 (7)	0.3143 (7)	0.4439 (7)	0.0447 (11)
C1	0.1758 (12)	0.5982 (12)	0.8836 (9)	0.0636 (19)
H1	0.1862	0.5294	0.9393	0.076*
C2	0.1428 (12)	0.7553 (13)	0.9537 (9)	0.069 (2)
H2	0.1285	0.7920	1.0537	0.083*
H2B	0.186 (18)	0.662 (18)	0.464 (16)	0.10 (4)*
C3	0.1312 (11)	0.8591 (11)	0.8713 (9)	0.0624 (18)
H3	0.1115	0.9683	0.9157	0.075*
C4	0.1493 (9)	0.7975 (9)	0.7231 (8)	0.0514 (14)
H4	0.1379	0.8635	0.6649	0.062*
C5	0.1848 (7)	0.6352 (7)	0.6597 (7)	0.0398 (11)
C6	0.2674 (7)	0.4531 (7)	0.4151 (7)	0.0395 (10)
C7	0.3045 (9)	0.4711 (10)	0.2836 (7)	0.0499 (13)
H7	0.2849	0.5656	0.2627	0.060*
C8	0.3715 (12)	0.3449 (13)	0.1842 (10)	0.067 (2)
H8	0.4006	0.3559	0.0977	0.080*
C9	0.3935 (9)	0.2066 (10)	0.2156 (9)	0.0587 (18)
H9	0.4365	0.1208	0.1498	0.070*
C10	0.3524 (9)	0.1931 (9)	0.3444 (10)	0.0556 (16)
H10	0.3694	0.0976	0.3648	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0618 (2)	0.0660 (2)	0.0781 (3)	0.02555 (14)	0.02487 (14)	0.04774 (18)
Cl1	0.0653 (11)	0.0710 (11)	0.0816 (13)	0.0210 (9)	0.0091 (9)	0.0445 (10)
Cl2	0.0623 (9)	0.0551 (8)	0.0628 (9)	0.0170 (7)	0.0277 (7)	0.0314 (7)
N1	0.051 (3)	0.058 (3)	0.050 (3)	0.019 (2)	0.014 (2)	0.027 (2)
N2	0.059 (3)	0.043 (2)	0.045 (3)	0.016 (2)	0.015 (2)	0.024 (2)
N3	0.043 (2)	0.041 (2)	0.056 (3)	0.006 (2)	0.013 (2)	0.023 (2)
C1	0.072 (5)	0.078 (5)	0.051 (4)	0.020 (4)	0.017 (3)	0.033 (4)
C2	0.071 (5)	0.084 (6)	0.047 (4)	0.019 (4)	0.012 (3)	0.017 (4)
C3	0.066 (4)	0.061 (4)	0.052 (4)	0.013 (4)	0.015 (3)	0.009 (3)
C4	0.053 (3)	0.045 (3)	0.052 (3)	0.007 (3)	0.008 (3)	0.014 (3)
C5	0.035 (2)	0.043 (3)	0.043 (3)	0.006 (2)	0.007 (2)	0.019 (2)
C6	0.037 (2)	0.040 (3)	0.042 (3)	0.005 (2)	0.008 (2)	0.017 (2)
C7	0.052 (3)	0.060 (4)	0.046 (3)	0.017 (3)	0.015 (2)	0.026 (3)
C8	0.064 (4)	0.088 (6)	0.057 (4)	0.013 (4)	0.025 (3)	0.032 (4)
C9	0.045 (3)	0.054 (4)	0.063 (4)	0.008 (3)	0.018 (3)	0.003 (3)
C10	0.049 (3)	0.047 (3)	0.072 (4)	0.011 (3)	0.020 (3)	0.021 (3)

Geometric parameters (Å, º) top

Cl1—Hg1	2.3875 (19)	C5—N1	1.323 (8)
Cl2—Hg1	2.4579 (19)	C5—N2	1.381 (8)
N1—Hg1	2.369 (6)	C6—N3	1.341 (8)
N2—H2B	0.95 (14)	C6—N2	1.383 (8)
N3—Hg1	2.290 (6)	C6—C7	1.398 (9)
C1—N1	1.349 (10)	C7—C8	1.397 (11)
C1—C2	1.363 (13)	C7—H7	0.9300
C1—H1	0.9300	C8—C9	1.352 (14)
C2—C3	1.390 (14)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.369 (12)
C3—C4	1.372 (11)	C9—H9	0.9300
C3—H3	0.9300	C10—N3	1.362 (9)
C4—C5	1.399 (9)	C10—H10	0.9300
C4—H4	0.9300

N1—Hg1—Cl1	112.30 (15)	N2—C6—C7	116.6 (5)
N1—Hg1—Cl2	94.92 (15)	C8—C7—C6	119.0 (7)
N3—Hg1—Cl1	112.21 (15)	C8—C7—H7	120.5
N3—Hg1—Cl2	123.92 (14)	C6—C7—H7	120.5
N3—Hg1—N1	82.4 (2)	C9—C8—C7	119.0 (7)
Cl1—Hg1—Cl2	120.14 (7)	C9—C8—H8	120.6
N1—C1—C2	123.8 (8)	C7—C8—H8	120.4
N1—C1—H1	118.1	C8—C9—C10	119.9 (7)
C2—C1—H1	118.1	C8—C9—H9	120.0
C1—C2—C3	117.9 (8)	C10—C9—H9	120.1
C1—C2—H2	121.0	N3—C10—C9	122.5 (7)
C3—C2—H2	121.0	N3—C10—H10	118.7
C4—C3—C2	118.7 (8)	C9—C10—H10	118.8
C4—C3—H3	120.6	C5—N1—C1	118.4 (7)
C2—C3—H3	120.7	C5—N1—Hg1	125.5 (4)
C3—C4—C5	119.9 (7)	C1—N1—Hg1	115.7 (5)
C3—C4—H4	120.1	C6—N2—C5	136.0 (5)
C5—C4—H4	120.0	C6—N2—H2B	109 (8)
N1—C5—N2	122.3 (6)	C5—N2—H2B	115 (8)
N1—C5—C4	121.1 (6)	C6—N3—C10	118.2 (6)
N2—C5—C4	116.6 (6)	C6—N3—Hg1	127.3 (4)
N3—C6—N2	122.1 (6)	C10—N3—Hg1	114.4 (5)
N3—C6—C7	121.3 (6)

C1—N1—Hg1—N3	−169.7 (6)	C6—C7—C8—C9	2.0 (12)
C5—N1—Hg1—N3	17.3 (5)	C7—C8—C9—C10	−0.9 (13)
C1—N1—Hg1—Cl1	−58.7 (6)	C8—C9—C10—N3	0.6 (12)
C1—N1—Hg1—Cl2	66.7 (6)	N2—C5—N1—C1	179.1 (7)
C5—N1—Hg1—Cl1	128.2 (5)	C4—C5—N1—C1	−2.6 (10)
C5—N1—Hg1—Cl2	−106.3 (5)	N2—C5—N1—Hg1	−8.1 (9)
C6—N3—Hg1—N1	−15.5 (5)	C4—C5—N1—Hg1	170.3 (5)
C10—N3—Hg1—N1	168.0 (5)	C2—C1—N1—C5	1.9 (13)
C6—N3—Hg1—Cl1	−126.5 (5)	C2—C1—N1—Hg1	−171.6 (7)
C10—N3—Hg1—Cl1	57.0 (5)	N3—C6—N2—C5	17.7 (11)
C6—N3—Hg1—Cl2	75.3 (5)	C7—C6—N2—C5	−164.1 (7)
C10—N3—Hg1—Cl2	−101.2 (5)	N1—C5—N2—C6	−15.3 (11)
N1—C1—C2—C3	−1.4 (15)	C4—C5—N2—C6	166.3 (7)
C1—C2—C3—C4	1.5 (14)	N2—C6—N3—C10	−179.2 (6)
C2—C3—C4—C5	−2.3 (12)	C7—C6—N3—C10	2.7 (9)
C3—C4—C5—N1	2.8 (10)	N2—C6—N3—Hg1	4.5 (8)
C3—C4—C5—N2	−178.7 (7)	C7—C6—N3—Hg1	−173.7 (5)
N3—C6—C7—C8	−3.0 (10)	C9—C10—N3—C6	−1.5 (10)
N2—C6—C7—C8	178.7 (7)	C9—C10—N3—Hg1	175.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl2ⁱ	0.95 (16)	2.41 (16)	3.345 (6)	169 (13)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[HgCl₂(C₁₀H₉N₃)]
M_r	442.69
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.0268 (12), 8.6127 (11), 9.6118 (14)
α, β, γ (°)	110.606 (11), 98.958 (12), 96.862 (11)
V (Å³)	603.38 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	13.17
Crystal size (mm)	0.24 × 0.21 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.061, 0.142
No. of measured, independent and observed [I > 2σ(I)] reflections	7105, 3214, 2806
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.126, 1.05
No. of reflections	3214
No. of parameters	150
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.43, −2.08

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

Selected geometric parameters (Å, º) top

Cl1—Hg1	2.3875 (19)	N1—Hg1	2.369 (6)
Cl2—Hg1	2.4579 (19)	N3—Hg1	2.290 (6)

N1—Hg1—Cl1	112.30 (15)	N3—Hg1—Cl2	123.92 (14)
N1—Hg1—Cl2	94.92 (15)	N3—Hg1—N1	82.4 (2)
N3—Hg1—Cl1	112.21 (15)	Cl1—Hg1—Cl2	120.14 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···Cl2ⁱ	0.95 (16)	2.41 (16)	3.345 (6)	169 (13)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

Ahmadi, R., Ebadi, A., Kalateh, K., Norouzi, A. & Amani, V. (2008). Acta Cryst. E64, m1407. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, W. T., Wang, M. S., Liu, X., Guo, G. C. & Huang, J. S. (2006). Cryst. Growth Des. 6, 2289–2300. Web of Science CSD CrossRef CAS 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
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
Kalateh, K., Norouzi, A., Ebadi, A., Ahmadi, R. & Amani, V. (2008). Acta Cryst. E64, m1583–m1584. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Khavasi, H. R., Abedi, A., Amani, V., Notash, B. & Safari, N. (2008). Polyhedron, 27, 1848–1854. Web of Science CSD CrossRef CAS Google Scholar
Liu, Q. D., Wang, R. & Wang, S. (2004). Dalton Trans. pp. 2073–2079. Web of Science CSD CrossRef PubMed Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yousefi, M., Rashidi Vahid, R., Amani, V., Arab Chamjangali, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m1339–m1340. 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