(5,5′-Dimethyl-2,2′-bipyridine-κ2N,N′)diiodidomercury(II)

Tadayon Pour, N.; Ebadi, A.; Abedi, A.; Amani, V.; Khavasi, H.R.

doi:10.1107/S160053680802953X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1305

doi:10.1107/S160053680802953X

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(5,5′-Dimethyl-2,2′-bipyridine-κ²N,N′)diiodidomercury(II)

Nasim Tadayon Pour,^a Amin Ebadi,^b Anita Abedi,^c Vahid Amani ^a ^* and Hamid Reza Khavasi ^d

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, ^bDepartment of Chemistry, Islamic Azad University, Kazeroon Branch, Kazeroon, Fars, Iran, ^cDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^dDepartment of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran
^*Correspondence e-mail: v_amani2002@yahoo.com

(Received 13 September 2008; accepted 15 September 2008; online 20 September 2008)

In the molecule of the title compound, [HgI₂(C₁₂H₁₂N₂)], the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 5,5′-dimethyl-2,2′-bipyridine and two I atoms. There is a π–π contact between pyridine rings of adjacent molecules [centroid–centroid distance = 3.723 (5) Å].

Related literature

For related literature, see: Ahmadi, Kalateh et al. (2008 ); Ahmadi, Khalighi et al. (2008 ); Chen et al. (2006 ); Freire et al. (1999 ); Htoon & Ladd (1976 ); Khalighi et al. (2008 ); Khavasi et al. (2008 ); Yousefi, Khalighi, et al. (2008 ); Yousefi, Tadayon Pour et al. (2008 ).

Experimental

Crystal data

[HgI₂(C₁₂H₁₂N₂)]
M_r = 638.63
Orthorhombic, P b c a
a = 15.0325 (8) Å
b = 15.0654 (8) Å
c = 14.0579 (10) Å
V = 3183.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 13.53 mm⁻¹
T = 298 (2) K
0.35 × 0.31 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005)] T_min = 0.015, T_max = 0.075
23007 measured reflections
4306 independent reflections
3418 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.124
S = 1.19
4306 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 1.44 e Å⁻³
Δρ_min = −1.51 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Hg1—I1	2.6587 (9)
Hg1—I2	2.6684 (8)
Hg1—N1	2.377 (7)
Hg1—N2	2.389 (6)

I1—Hg1—I2	129.89 (3)
N1—Hg1—I1	113.59 (16)
N1—Hg1—N2	69.7 (2)
N1—Hg1—I2	106.53 (16)
N2—Hg1—I1	107.15 (15)
N2—Hg1—I2	114.22 (15)

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 datablock I. DOI: 10.1107/S160053680802953X/hk2531sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802953X/hk2531Isup2.hkl

checkCIF report

Comment top

Recently, we reported the syntheses and crystal structures of [Zn(5,5'-dmbpy)Cl₂], (II), (Khalighi et al., 2008), [Zn(6-mbpy)Cl₂], (III), (Ahmadi, Kalateh et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)₂]_n, (IV), (Ahmadi, Khalighi et al., 2008), [Cu(5,5'-dcbpy)(en)(H₂O)₂].2.5H₂O, (V), (Yousefi, Khalighi et al., 2008) and {[HgCl(dm4bt)]₂(µ-Cl)₂}, (VI), (Khavasi et al., 2008) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2' -bipyridine, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-dicarboxylate, en is ethylene- diamine and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. There are several Hg^II complexes, with formula, [HgI₂(N—N)], such as [HgI₂(bipy)], (VII), [HgI₂(phen)], (VIII) and [HgI₂(2,9-dmphen)], (IX), (Freire et al., 1999), [HgI₂(bipy)][HgI₂], (X), (Chen et al., 2006), [HgI₂(4,4'-dmbpy)], (XI), (Yousefi, Tadayon Pour et al., 2008) and [HgI₂(TMDA)], (XII), (Htoon & Ladd, 1976) [where bipy is 2,2'-bipyridine, phen is 1,10-phenanthroline, dmphen is 2,9-dimethyl-1,10-phenanthroline, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine and TMDA is tetramethylethylene- diamine] 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 5,5'-dimethyl-2,2'-bi- pyridine and two I atoms. The Hg—I and Hg—N bond lengths and angles (Table 1) are within normal ranges, as in (VII), (VIII) and (XI).

In the crystal structure, the π-π contact (Fig. 2) between the pyridine rings, Cg2···Cg3ⁱ [symmetry code: (i) x, 1 - y, 1 - z, where Cg2 and Cg3 are centroids of the rings (N1/C1/C2/C4-C6) and (N2/C7-C10/C12), respectively] may stabilize the structure, with centroid-centroid distance of 3.723 (5) Å.

Related literature top

For related literature, see: Ahmadi, Kalateh et al. (2008); Ahmadi, Khalighi et al. (2008); Chen et al. (2006); Freire et al. (1999); Htoon & Ladd (1976); Khalighi et al. (2008); Khavasi et al. (2008); Yousefi, Khalighi, et al. (2008); Yousefi, Tadayon Pour et al. (2008).

Experimental top

For the preparation of the title compound, (I), a solution of 5,5'-dimethyl -2,2'-bipyridine (0.25 g, 1.33 mmol) in methanol (10 ml) was added to a solution of HgI₂ (0.61 g, 1.33 mmol) in methanol (5 ml) at room temperature. The suitable crystals for X-ray analysis were isolated after one week by methanol diffusion to a colorless solution in DMSO (yield; 0.62 g, 72.9%).

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.

(5,5'-Dimethyl-2,2'-bipyridine-κ²N,N')diiodidomercury(II) top

Crystal data top

[HgI₂(C₁₂H₁₂N₂)]	F(000) = 2272
M_r = 638.63	D_x = 2.665 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1768 reflections
a = 15.0325 (8) Å	θ = 2.4–29.3°
b = 15.0654 (8) Å	µ = 13.53 mm⁻¹
c = 14.0579 (10) Å	T = 298 K
V = 3183.7 (3) Å³	Prism, colorless
Z = 8	0.35 × 0.31 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4306 independent reflections
Radiation source: fine-focus sealed tube	3418 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
ϕ and ω scans	θ_max = 29.3°, θ_min = 2.4°
Absorption correction: numerical shape of crystal determined optically (X-SHAPE and X-RED32; Stoe& Cie, 2005)	h = −20→19
T_min = 0.015, T_max = 0.075	k = −20→17
23007 measured reflections	l = −19→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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0347P)² + 17.4498P] where P = (F_o² + 2F_c²)/3
4306 reflections	(Δ/σ)_max = 0.010
154 parameters	Δρ_max = 1.44 e Å⁻³
0 restraints	Δρ_min = −1.51 e Å⁻³

Crystal data top

[HgI₂(C₁₂H₁₂N₂)]	V = 3183.7 (3) Å³
M_r = 638.63	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.0325 (8) Å	µ = 13.53 mm⁻¹
b = 15.0654 (8) Å	T = 298 K
c = 14.0579 (10) Å	0.35 × 0.31 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4306 independent reflections
Absorption correction: numerical shape of crystal determined optically (X-SHAPE and X-RED32; Stoe& Cie, 2005)	3418 reflections with I > 2σ(I)
T_min = 0.015, T_max = 0.075	R_int = 0.083
23007 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0347P)² + 17.4498P] where P = (F_o² + 2F_c²)/3
4306 reflections	Δρ_max = 1.44 e Å⁻³
154 parameters	Δρ_min = −1.51 e Å⁻³

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	0.11964 (2)	0.71065 (2)	0.60202 (3)	0.05197 (12)
I1	0.00810 (7)	0.80915 (5)	0.50004 (7)	0.0859 (3)
I2	0.25140 (5)	0.76000 (5)	0.71769 (6)	0.0687 (2)
N1	0.1696 (4)	0.5812 (5)	0.5214 (5)	0.0403 (14)
N2	0.0387 (4)	0.5836 (4)	0.6554 (5)	0.0381 (13)
C1	0.2371 (5)	0.5833 (6)	0.4598 (6)	0.0463 (18)
H1	0.2633	0.6377	0.4460	0.056*
C2	0.2697 (6)	0.5082 (7)	0.4155 (6)	0.049 (2)
C3	0.3485 (8)	0.5156 (9)	0.3481 (9)	0.077 (3)
H3A	0.3986	0.5399	0.3816	0.093*
H3B	0.3333	0.5538	0.2959	0.093*
H3C	0.3635	0.4578	0.3243	0.093*
C4	0.2299 (7)	0.4279 (7)	0.4391 (8)	0.063 (3)
H4	0.2506	0.3755	0.4121	0.076*
C5	0.1604 (7)	0.4257 (6)	0.5019 (7)	0.053 (2)
H5	0.1324	0.3723	0.5162	0.063*
C6	0.1322 (5)	0.5044 (5)	0.5440 (5)	0.0387 (16)
C7	0.0586 (5)	0.5057 (5)	0.6156 (5)	0.0378 (15)
C8	0.0140 (6)	0.4291 (6)	0.6412 (7)	0.054 (2)
H8	0.0270	0.3754	0.6118	0.065*
C9	−0.0503 (6)	0.4341 (6)	0.7113 (7)	0.054 (2)
H9	−0.0805	0.3829	0.7297	0.065*
C10	−0.0703 (6)	0.5135 (6)	0.7542 (6)	0.0477 (19)
C11	−0.1370 (7)	0.5206 (8)	0.8337 (8)	0.069 (3)
H11A	−0.1831	0.5615	0.8159	0.083*
H11B	−0.1078	0.5417	0.8901	0.083*
H11C	−0.1625	0.4633	0.8458	0.083*
C12	−0.0244 (5)	0.5873 (6)	0.7226 (6)	0.0465 (18)
H12	−0.0379	0.6422	0.7492	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0544 (2)	0.04113 (17)	0.0603 (2)	0.00092 (15)	0.00422 (17)	−0.00082 (14)
I1	0.0978 (6)	0.0521 (4)	0.1078 (7)	0.0131 (4)	−0.0354 (5)	0.0050 (4)
I2	0.0660 (4)	0.0555 (4)	0.0845 (5)	0.0031 (3)	−0.0154 (4)	−0.0110 (3)
N1	0.039 (3)	0.044 (3)	0.037 (3)	0.001 (3)	0.003 (3)	−0.002 (3)
N2	0.035 (3)	0.039 (3)	0.041 (3)	0.002 (3)	0.000 (3)	0.001 (3)
C1	0.040 (4)	0.053 (5)	0.046 (4)	−0.002 (4)	0.009 (3)	−0.006 (4)
C2	0.041 (4)	0.072 (6)	0.035 (4)	0.012 (4)	0.000 (3)	−0.002 (4)
C3	0.061 (6)	0.098 (9)	0.073 (7)	0.016 (6)	0.029 (6)	−0.004 (6)
C4	0.070 (7)	0.058 (6)	0.062 (6)	0.019 (5)	0.001 (5)	−0.020 (5)
C5	0.058 (5)	0.045 (4)	0.056 (5)	0.003 (4)	0.004 (4)	−0.002 (4)
C6	0.038 (4)	0.038 (4)	0.040 (4)	0.001 (3)	−0.004 (3)	−0.002 (3)
C7	0.039 (4)	0.040 (4)	0.035 (4)	0.003 (3)	−0.009 (3)	−0.001 (3)
C8	0.057 (5)	0.047 (5)	0.058 (5)	−0.009 (4)	−0.004 (4)	−0.002 (4)
C9	0.051 (5)	0.051 (5)	0.062 (6)	−0.016 (4)	0.003 (4)	0.007 (4)
C10	0.038 (4)	0.057 (5)	0.048 (5)	−0.001 (4)	−0.005 (3)	0.010 (4)
C11	0.059 (6)	0.080 (7)	0.067 (6)	−0.001 (5)	0.031 (5)	0.000 (5)
C12	0.042 (4)	0.048 (4)	0.050 (5)	0.003 (4)	0.009 (4)	−0.003 (4)

Geometric parameters (Å, º) top

Hg1—I1	2.6587 (9)	C6—N1	1.325 (10)
Hg1—I2	2.6684 (8)	C6—C7	1.496 (11)
Hg1—N1	2.377 (7)	C7—N2	1.335 (10)
Hg1—N2	2.389 (6)	C7—C8	1.382 (12)
C1—N1	1.335 (10)	C8—C9	1.384 (14)
C1—C2	1.380 (13)	C8—H8	0.9300
C1—H1	0.9300	C9—C10	1.373 (13)
C2—C4	1.390 (15)	C9—H9	0.9300
C2—C3	1.521 (13)	C10—C12	1.382 (12)
C3—H3A	0.9600	C10—C11	1.505 (13)
C3—H3B	0.9600	C11—H11A	0.9600
C3—H3C	0.9600	C11—H11B	0.9600
C4—C5	1.368 (14)	C11—H11C	0.9600
C4—H4	0.9300	C12—N2	1.339 (10)
C5—C6	1.392 (11)	C12—H12	0.9300
C5—H5	0.9300

I1—Hg1—I2	129.89 (3)	C4—C5—C6	119.1 (9)
N1—Hg1—I1	113.59 (16)	C4—C5—H5	120.5
N1—Hg1—N2	69.7 (2)	C6—C5—H5	120.5
N1—Hg1—I2	106.53 (16)	N1—C6—C5	120.9 (8)
N2—Hg1—I1	107.15 (15)	N1—C6—C7	117.6 (7)
N2—Hg1—I2	114.22 (15)	C5—C6—C7	121.5 (7)
C1—N1—Hg1	122.0 (6)	N2—C7—C8	121.1 (8)
C6—N1—Hg1	117.9 (5)	N2—C7—C6	117.4 (7)
C6—N1—C1	119.9 (7)	C8—C7—C6	121.5 (7)
C7—N2—Hg1	117.3 (5)	C7—C8—C9	118.7 (9)
C7—N2—C12	119.4 (7)	C7—C8—H8	120.7
C12—N2—Hg1	123.3 (5)	C9—C8—H8	120.7
N1—C1—C2	122.9 (9)	C10—C9—C8	120.8 (8)
N1—C1—H1	118.5	C10—C9—H9	119.6
C2—C1—H1	118.5	C8—C9—H9	119.6
C1—C2—C4	116.9 (8)	C9—C10—C12	116.8 (8)
C1—C2—C3	119.9 (10)	C9—C10—C11	122.3 (9)
C4—C2—C3	123.2 (9)	C12—C10—C11	120.9 (9)
C2—C3—H3A	109.5	C10—C11—H11A	109.5
C2—C3—H3B	109.5	C10—C11—H11B	109.5
H3A—C3—H3B	109.5	H11A—C11—H11B	109.5
C2—C3—H3C	109.5	C10—C11—H11C	109.5
H3A—C3—H3C	109.5	H11A—C11—H11C	109.5
H3B—C3—H3C	109.5	H11B—C11—H11C	109.5
C5—C4—C2	120.3 (9)	N2—C12—C10	123.2 (8)
C5—C4—H4	119.8	N2—C12—H12	118.4
C2—C4—H4	119.8	C10—C12—H12	118.4

I1—Hg1—N1—C1	82.9 (6)	C5—C6—N1—C1	−2.1 (12)
I1—Hg1—N1—C6	−101.5 (5)	C7—C6—N1—C1	178.3 (7)
I2—Hg1—N1—C1	−66.4 (6)	C5—C6—N1—Hg1	−177.8 (6)
I2—Hg1—N1—C6	109.2 (5)	C7—C6—N1—Hg1	2.6 (9)
N2—Hg1—N1—C1	−176.7 (7)	N1—C6—C7—N2	−3.3 (11)
N2—Hg1—N1—C6	−1.1 (5)	C5—C6—C7—N2	177.1 (8)
I1—Hg1—N2—C7	108.7 (5)	N1—C6—C7—C8	178.0 (8)
I1—Hg1—N2—C12	−71.7 (6)	C5—C6—C7—C8	−1.6 (12)
I2—Hg1—N2—C7	−100.3 (5)	C8—C7—N2—C12	1.4 (12)
I2—Hg1—N2—C12	79.3 (6)	C6—C7—N2—C12	−177.3 (7)
N1—Hg1—N2—C7	−0.8 (5)	C8—C7—N2—Hg1	−179.0 (6)
N1—Hg1—N2—C12	178.9 (7)	C6—C7—N2—Hg1	2.3 (9)
C2—C1—N1—C6	1.5 (13)	N2—C7—C8—C9	−1.9 (13)
C2—C1—N1—Hg1	177.0 (6)	C6—C7—C8—C9	176.7 (8)
N1—C1—C2—C4	−1.1 (13)	C7—C8—C9—C10	0.6 (15)
N1—C1—C2—C3	−178.3 (9)	C8—C9—C10—C12	1.2 (14)
C1—C2—C4—C5	1.4 (14)	C8—C9—C10—C11	−177.2 (9)
C3—C2—C4—C5	178.5 (10)	C9—C10—C12—N2	−1.8 (13)
C2—C4—C5—C6	−2.1 (15)	C11—C10—C12—N2	176.6 (9)
C4—C5—C6—N1	2.5 (14)	C10—C12—N2—C7	0.6 (13)
C4—C5—C6—C7	−178.0 (8)	C10—C12—N2—Hg1	−179.1 (6)

Experimental details

Crystal data
Chemical formula	[HgI₂(C₁₂H₁₂N₂)]
M_r	638.63
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	15.0325 (8), 15.0654 (8), 14.0579 (10)
V (Å³)	3183.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	13.53
Crystal size (mm)	0.35 × 0.31 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Numerical shape of crystal determined optically (X-SHAPE and X-RED32; Stoe& Cie, 2005)
T_min, T_max	0.015, 0.075
No. of measured, independent and observed [I > 2σ(I)] reflections	23007, 4306, 3418
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.124, 1.19
No. of reflections	4306
No. of parameters	154
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0347P)² + 17.4498P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.44, −1.51

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

Hg1—I1	2.6587 (9)	Hg1—N1	2.377 (7)
Hg1—I2	2.6684 (8)	Hg1—N2	2.389 (6)

I1—Hg1—I2	129.89 (3)	N1—Hg1—I2	106.53 (16)
N1—Hg1—I1	113.59 (16)	N2—Hg1—I1	107.15 (15)
N1—Hg1—N2	69.7 (2)	N2—Hg1—I2	114.22 (15)

Acknowledgements

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

References

Ahmadi, R., Kalateh, K., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1266. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233. Web of Science CSD CrossRef IUCr Journals 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
Freire, E., Baggio, S., Baggio, R. & Suescun, L. (1999). J. Chem. Crystallogr. 29, 825–830. Web of Science CSD CrossRef CAS Google Scholar
Htoon, S. & Ladd, M. F. C. (1976). J. Cryst. Mol. Struct. 6, 55-58. CSD CrossRef CAS Web of Science Google Scholar
Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211–m1212. 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar
Yousefi, M., Khalighi, A., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1284–m1285. 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