Crystal structure of bis­(3-bromo­pyridine-κN)bis­(O-ethyl di­thio­carbonato-κ2S,S′)nickel(II)

Kant, R.; Kour, G.; Anthal, S.; Neerupama; Sachar, R.

doi:10.1107/S2056989014027339

metal-organic compounds

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Volume 71| Part 1| January 2015| Pages m12-m13

https://doi.org/10.1107/S2056989014027339

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Crystal structure of bis(3-bromopyridine-κN)bis(O-ethyl dithiocarbonato-κ²S,S′)nickel(II)

Rajni Kant,^a ^* Gurvinder Kour,^a Sumati Anthal,^a Neerupama ^b and Renu Sachar ^b

^aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bPost-Graduate Department of Chemistry, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: rkant.ju@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 3 December 2014; accepted 15 December 2014; online 1 January 2015)

In the title molecular complex, [Ni(C₃H₅OS₂)₂(C₅H₄BrN)₂], the Ni²⁺ cation is located on a centre of inversion and has a distorted octahedral N₂S₄ environment defined by two chelating xanthate ligands and two monodentate pyridine ligands. The C—S bond lengths of the thiocarboxylate group are indicative of a delocalized bond and the O—Csp² bond is considerably shorter than the O—Csp³ bond, consistent with a significant contribution of one resonance form of the xanthate anion that features a formal C=O₊ unit and a negative charge on each of the S atoms. The packing of the molecules is stabilized by C—H⋯S and C—H⋯π interactions. In addition, π–π interactions between the pyridine rings [centroid-to-centroid distance = 3.797 (3) Å] are also present. In the crystal structure, molecules are arranged in rows along [100], forming layers parallel to (010) and (001).

Keywords: Crystal structure; nickel complex; xanthate ligands; π–π interactions; crystal structure.

CCDC reference: 1036070

1. Related literature

Xanthates as ligands have been investigated extensively due to their coordination behaviour (Haiduc et al., 1995 ), thereby showing monodentate and/or bidentate coordination modes (Xiong et al., 1997 ; Trávnícek et al., 1995 ). Xanthates have also found uses as antitumour agents and in the treatment of Alzheimer's disease (Orts et al., 2002 ; Larsson & Öberg, 2011 ). For other analogous Ni–dithiocarboxylate complexes, see: Kapoor et al. (2012 ). For C—S and C—O bond lengths in other xanthates, see: Jiang et al. (2002 ); Alam et al. (2011 ).

2. Experimental

2.1. Crystal data

[Ni(C₃H₅OS₂)₂(C₅H₄BrN)₂]
M_r = 617.09
Triclinic, $[P \overline 1]$
a = 6.8397 (7) Å
b = 9.1952 (8) Å
c = 9.7562 (10) Å
α = 76.121 (8)°
β = 73.935 (9)°
γ = 78.517 (8)°
V = 566.59 (10) Å³
Z = 1
Mo Kα radiation
μ = 4.77 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

2.2. Data collection

Oxford Diffraction Xcalibur CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.489, T_max = 1.000
4016 measured reflections
2230 independent reflections
1510 reflections with I > 2σ(I)
R_int = 0.044

2.3. Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.112
S = 1.03
2230 reflections
126 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.118 (4)
Ni1—S2	2.4314 (12)
Ni1—S1	2.4368 (12)
S2—C6	1.691 (5)
S1—C6	1.679 (5)
C6—O1	1.328 (5)
C7—O1	1.447 (5)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/C2/C3/C4/C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯S2ⁱ	0.93	2.78	3.642 (5)	154
C8—H8A⋯Cg1ⁱⁱ	0.96	3.26	3.712 (6)	111
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

CCDC reference: 1036070

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989014027339/wm5101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014027339/wm5101Isup2.hkl

checkCIF report

Related literature top

Xanthates as ligands have been investigated extensively due to their coordination behaviour (Haiduc et al., 1995), thereby showing monodentate and/or bidentate coordination modes (Xiong et al., 1997; Trávní˘cek et al., 1995). Xanthates have also found uses as antitumour agents and in the treatment of Alzheimer's disease (Orts et al., 2002; Larsson & Oberg, 2011). For other analogous Ni–dithiocarboxylate complexes, see: Kapoor et al. (2012). For C—S and C—O bond lengths in other xanthates, see: Jiang et al. (2002); Alam et al. (2011).

Experimental top

Bis(O-ethyldithiocarbonato)nickel(II) required for preparation of the adduct was obtained by mixing aqueous solutions of the potassium salt of O-ethyldithiocarbonate (3.24 g, 0.02 mol) and NiCl₂·6H₂O (2.37 g, 0.01 mol). The formed bis(O-ethyldithiocarbonato)nickel(II) precipitate was immediately filtered off and dried in a vacuum desiccator. Bis(O-ethyldithiocarbonato)nickel(II) (0.783 g, 0.0026 mol) was then dissolved in acetone (60 ml) and stirred for about 10–20 minutes. To the resulting solution, 3-bromopyridine (0.82 g, 0.0052 mol) was added. The mixture was stirred for additional two to three hours and kept undisturbed for one to two days when dark green coloured crystals of the adduct had formed. The product so obtained was filtered and dried in vacuum desiccator over anhydrous calcium chloride.

Structure description top

Xanthates as ligands have been investigated extensively due to their coordination behaviour (Haiduc et al., 1995), thereby showing monodentate and/or bidentate coordination modes (Xiong et al., 1997; Trávní˘cek et al., 1995). Xanthates have also found uses as antitumour agents and in the treatment of Alzheimer's disease (Orts et al., 2002; Larsson & Oberg, 2011). For other analogous Ni–dithiocarboxylate complexes, see: Kapoor et al. (2012). For C—S and C—O bond lengths in other xanthates, see: Jiang et al. (2002); Alam et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radius. All non-labelled atoms are related by symmetry code (-x+1, -y, -z).
	Fig. 2. The packing arrangement of molecules of the title compound viewed down [100].

Bis(3-bromopyridine-κN)bis(O-ethyl dithiocarbonato-κ²S,S')nickel(II) top

Crystal data top

[Ni(C₃H₅OS₂)₂(C₅H₄BrN)₂]	Z = 1
M_r = 617.09	F(000) = 306
Triclinic, P1	D_x = 1.809 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8397 (7) Å	Cell parameters from 1227 reflections
b = 9.1952 (8) Å	θ = 4.1–27.4°
c = 9.7562 (10) Å	µ = 4.77 mm⁻¹
α = 76.121 (8)°	T = 293 K
β = 73.935 (9)°	Block, dark green
γ = 78.517 (8)°	0.3 × 0.2 × 0.1 mm
V = 566.59 (10) Å³

Data collection top

Oxford Diffraction Xcalibur CCD diffractometer	2230 independent reflections
Radiation source: fine-focus sealed tube	1510 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 26.0°, θ_min = 3.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −6→8
T_min = 0.489, T_max = 1.000	k = −9→11
4016 measured reflections	l = −11→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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0339P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2230 reflections	Δρ_max = 0.67 e Å⁻³
126 parameters	Δρ_min = −0.68 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (18)

Crystal data top

[Ni(C₃H₅OS₂)₂(C₅H₄BrN)₂]	γ = 78.517 (8)°
M_r = 617.09	V = 566.59 (10) Å³
Triclinic, P1	Z = 1
a = 6.8397 (7) Å	Mo Kα radiation
b = 9.1952 (8) Å	µ = 4.77 mm⁻¹
c = 9.7562 (10) Å	T = 293 K
α = 76.121 (8)°	0.3 × 0.2 × 0.1 mm
β = 73.935 (9)°

Data collection top

Oxford Diffraction Xcalibur CCD diffractometer	2230 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	1510 reflections with I > 2σ(I)
T_min = 0.489, T_max = 1.000	R_int = 0.044
4016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.67 e Å⁻³
2230 reflections	Δρ_min = −0.68 e Å⁻³
126 parameters

Special details top

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Ni1	0.5000	0.0000	0.0000	0.0371 (3)
Br1	0.31297 (11)	0.60432 (7)	−0.32487 (8)	0.0877 (3)
S2	0.85033 (18)	−0.09955 (15)	−0.11048 (14)	0.0456 (4)
S1	0.49994 (18)	−0.02146 (15)	−0.24413 (14)	0.0451 (4)
C4	0.7696 (8)	0.4151 (6)	−0.1093 (6)	0.0552 (15)
H4	0.8821	0.4427	−0.0908	0.066*
C6	0.7488 (7)	−0.0893 (5)	−0.2527 (5)	0.0418 (12)
C7	0.8014 (8)	−0.1290 (6)	−0.4944 (5)	0.0540 (15)
H7A	0.7966	−0.0258	−0.5491	0.065*
H7B	0.6644	−0.1570	−0.4674	0.065*
O1	0.8752 (5)	−0.1419 (4)	−0.3659 (3)	0.0484 (9)
C8	0.9484 (8)	−0.2339 (7)	−0.5834 (6)	0.0742 (19)
H8A	1.0845	−0.2083	−0.6050	0.111*
H8B	0.9089	−0.2248	−0.6724	0.111*
H8C	0.9463	−0.3361	−0.5299	0.111*
C1	0.4523 (7)	0.3245 (5)	−0.1639 (5)	0.0450 (13)
H1	0.3439	0.2931	−0.1841	0.054*
C5	0.7205 (7)	0.2725 (6)	−0.0545 (6)	0.0474 (13)
H5	0.7986	0.2055	0.0044	0.057*
C2	0.4894 (8)	0.4701 (6)	−0.2192 (5)	0.0479 (13)
C3	0.6516 (8)	0.5174 (6)	−0.1919 (6)	0.0565 (15)
H3	0.6801	0.6161	−0.2285	0.068*
N1	0.5662 (5)	0.2245 (4)	−0.0814 (4)	0.0392 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0384 (5)	0.0377 (5)	0.0395 (6)	0.0025 (4)	−0.0206 (4)	−0.0089 (4)
Br1	0.1128 (6)	0.0498 (4)	0.1009 (6)	−0.0010 (4)	−0.0560 (5)	0.0109 (4)
S2	0.0407 (7)	0.0547 (9)	0.0446 (8)	0.0053 (6)	−0.0205 (6)	−0.0137 (6)
S1	0.0465 (7)	0.0503 (8)	0.0439 (8)	0.0035 (7)	−0.0243 (6)	−0.0124 (6)
C4	0.048 (3)	0.057 (4)	0.065 (4)	−0.015 (3)	−0.002 (3)	−0.028 (3)
C6	0.046 (3)	0.042 (3)	0.034 (3)	−0.002 (2)	−0.008 (2)	−0.006 (2)
C7	0.061 (3)	0.064 (4)	0.037 (3)	−0.009 (3)	−0.008 (3)	−0.016 (3)
O1	0.0487 (19)	0.065 (2)	0.033 (2)	−0.0033 (18)	−0.0124 (16)	−0.0125 (18)
C8	0.097 (5)	0.077 (5)	0.049 (4)	−0.008 (4)	−0.010 (3)	−0.026 (3)
C1	0.053 (3)	0.043 (3)	0.044 (3)	−0.002 (3)	−0.019 (2)	−0.011 (3)
C5	0.041 (3)	0.051 (3)	0.054 (3)	−0.004 (3)	−0.015 (2)	−0.015 (3)
C2	0.059 (3)	0.040 (3)	0.041 (3)	−0.006 (3)	−0.009 (2)	−0.006 (2)
C3	0.068 (4)	0.040 (3)	0.061 (4)	−0.014 (3)	−0.009 (3)	−0.010 (3)
N1	0.040 (2)	0.039 (2)	0.043 (3)	−0.0020 (19)	−0.0167 (19)	−0.0109 (19)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	2.118 (4)	C7—C8	1.492 (6)
Ni1—N1	2.118 (4)	C7—H7A	0.9700
Ni1—S2ⁱ	2.4314 (12)	C7—H7B	0.9700
Ni1—S2	2.4314 (12)	C8—H8A	0.9600
Ni1—S1	2.4368 (12)	C8—H8B	0.9600
Ni1—S1ⁱ	2.4368 (12)	C8—H8C	0.9600
Br1—C2	1.878 (5)	C1—N1	1.344 (5)
S2—C6	1.691 (5)	C1—C2	1.364 (7)
S1—C6	1.679 (5)	C1—H1	0.9300
C4—C5	1.363 (7)	C5—N1	1.331 (6)
C4—C3	1.372 (8)	C5—H5	0.9300
C4—H4	0.9300	C2—C3	1.379 (7)
C6—O1	1.328 (5)	C3—H3	0.9300
C7—O1	1.447 (5)

N1ⁱ—Ni1—N1	180.0 (3)	O1—C7—H7B	110.4
N1ⁱ—Ni1—S2ⁱ	90.75 (10)	C8—C7—H7B	110.4
N1—Ni1—S2ⁱ	89.25 (10)	H7A—C7—H7B	108.6
N1ⁱ—Ni1—S2	89.25 (10)	C6—O1—C7	118.9 (3)
N1—Ni1—S2	90.75 (10)	C7—C8—H8A	109.5
S2ⁱ—Ni1—S2	180.00 (8)	C7—C8—H8B	109.5
N1ⁱ—Ni1—S1	90.29 (11)	H8A—C8—H8B	109.5
N1—Ni1—S1	89.71 (11)	C7—C8—H8C	109.5
S2ⁱ—Ni1—S1	106.15 (4)	H8A—C8—H8C	109.5
S2—Ni1—S1	73.85 (4)	H8B—C8—H8C	109.5
N1ⁱ—Ni1—S1ⁱ	89.71 (11)	N1—C1—C2	122.6 (5)
N1—Ni1—S1ⁱ	90.29 (11)	N1—C1—H1	118.7
S2ⁱ—Ni1—S1ⁱ	73.85 (4)	C2—C1—H1	118.7
S2—Ni1—S1ⁱ	106.15 (4)	N1—C5—C4	123.2 (5)
S1—Ni1—S1ⁱ	180.000 (5)	N1—C5—H5	118.4
C6—S2—Ni1	82.79 (15)	C4—C5—H5	118.4
C6—S1—Ni1	82.87 (17)	C1—C2—C3	119.3 (5)
C5—C4—C3	119.3 (5)	C1—C2—Br1	119.4 (4)
C5—C4—H4	120.3	C3—C2—Br1	121.2 (4)
C3—C4—H4	120.3	C4—C3—C2	118.2 (5)
O1—C6—S1	123.4 (3)	C4—C3—H3	120.9
O1—C6—S2	116.1 (3)	C2—C3—H3	120.9
S1—C6—S2	120.5 (3)	C5—N1—C1	117.4 (5)
O1—C7—C8	106.8 (4)	C5—N1—Ni1	122.2 (3)
O1—C7—H7A	110.4	C1—N1—Ni1	120.5 (3)
C8—C7—H7A	110.4

N1ⁱ—Ni1—S2—C6	89.6 (2)	N1—C1—C2—Br1	−176.7 (3)
N1—Ni1—S2—C6	−90.4 (2)	C5—C4—C3—C2	−1.5 (8)
S1—Ni1—S2—C6	−0.95 (18)	C1—C2—C3—C4	−0.1 (7)
S1ⁱ—Ni1—S2—C6	179.05 (18)	Br1—C2—C3—C4	177.5 (4)
N1ⁱ—Ni1—S1—C6	−88.2 (2)	C4—C5—N1—C1	−1.6 (7)
N1—Ni1—S1—C6	91.8 (2)	C4—C5—N1—Ni1	178.0 (4)
S2ⁱ—Ni1—S1—C6	−179.04 (18)	C2—C1—N1—C5	−0.1 (7)
S2—Ni1—S1—C6	0.96 (18)	C2—C1—N1—Ni1	−179.8 (3)
Ni1—S1—C6—O1	176.2 (4)	S2ⁱ—Ni1—N1—C5	125.0 (3)
Ni1—S1—C6—S2	−1.5 (3)	S2—Ni1—N1—C5	−55.0 (3)
Ni1—S2—C6—O1	−176.4 (4)	S1—Ni1—N1—C5	−128.9 (3)
Ni1—S2—C6—S1	1.5 (3)	S1ⁱ—Ni1—N1—C5	51.1 (3)
S1—C6—O1—C7	5.5 (6)	S2ⁱ—Ni1—N1—C1	−55.4 (3)
S2—C6—O1—C7	−176.7 (4)	S2—Ni1—N1—C1	124.6 (3)
C8—C7—O1—C6	−164.0 (5)	S1—Ni1—N1—C1	50.8 (3)
C3—C4—C5—N1	2.5 (8)	S1ⁱ—Ni1—N1—C1	−129.2 (3)
N1—C1—C2—C3	1.0 (7)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1/C2/C3/C4/C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···S2ⁱⁱ	0.93	2.78	3.642 (5)	154
C8—H8A···Cg1ⁱⁱⁱ	0.96	3.26	3.712 (6)	111

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

Selected bond lengths (Å) top

Ni1—N1	2.118 (4)	S1—C6	1.679 (5)
Ni1—S2	2.4314 (12)	C6—O1	1.328 (5)
Ni1—S1	2.4368 (12)	C7—O1	1.447 (5)
S2—C6	1.691 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1/C2/C3/C4/C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···S2ⁱ	0.93	2.78	3.642 (5)	154
C8—H8A···Cg1ⁱⁱ	0.96	3.26	3.712 (6)	111

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

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

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ISSN: 2056-9890

Volume 71| Part 1| January 2015| Pages m12-m13

https://doi.org/10.1107/S2056989014027339

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