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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): m481–m482.
Published online 2009 April 2. doi:  10.1107/S160053680901191X
PMCID: PMC2977549

Diaqua­bis(2-bromo­benzoato-κO)bis­(N,N-diethyl­nicotinamide-κN 1)zinc(II)

Abstract

In the centrosymmetric title complex, [Zn(C7H4BrO2)2(C10H14N2O)2(H2O)2], the ZnII atom is located on an inversion center. The asymmetric unit contains one 2-bromo­benzoate (BB), one diethyl­nicotinamide (DENA) ligand and one coordinating water molecule. The four O atoms in the equatorial plane around the Zn atom form a slightly distorted square-planar arrangement, while the slightly distorted octa­hedral coordination is completed by the two N atoms of the DENA ligands in the axial positions. The dihedral angle between the carboxyl group and the adjacent benzene ring is 85.51 (12)°, while the pyridine and benzene rings are oriented at a dihedral angle of 44.07 (6)°. In the crystal structure, O—H(...)O hydrogen bonds link the mol­ecules into infinite chains.

Related literature

For general backgroud, see: Antolini et al. (1982 [triangle]); Bigoli et al. (1972 [triangle]); Nadzhafov et al. (1981 [triangle]); Shnulin et al. (1981 [triangle]). For related structures, see: Hökelek et al. (1995 [triangle], 1997 [triangle], 2007 [triangle] 2008 [triangle]); (Hökelek & Necefoğlu (1996 [triangle], 1997 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m481-scheme1.jpg

Experimental

Crystal data

  • [Zn(C7H4BrO2)2(C10H14N2O)2(H2O)2]
  • M r = 857.91
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m481-efi1.jpg
  • a = 13.0037 (2) Å
  • b = 10.3387 (2) Å
  • c = 14.9365 (3) Å
  • β = 114.180 (1)°
  • V = 1831.90 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.91 mm−1
  • T = 100 K
  • 0.40 × 0.30 × 0.23 mm

Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.368, T max = 0.517
  • 16722 measured reflections
  • 4566 independent reflections
  • 3769 reflections with I > 2σ(I)
  • R int = 0.072

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.073
  • S = 0.98
  • 4566 reflections
  • 232 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.13 e Å−3
  • Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901191X/xu2502sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901191X/xu2502Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer.

supplementary crystallographic information

Comment

Transition metal complexes with biochemically active ligands frequently show interesting physical and/or chemical properties, as a result they may find applications in biological systems (Antolini et al., 1982). The structural functions and coordination relationships of the arylcarboxylate ion in transition metal complexes of benzoic acid derivatives change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the medium of the synthesis (Nadzhafov et al., 1981; Shnulin et al., 1981). The nicotinic acid derivative N,N-diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972).

The structure determination of the title compound, (I), a zinc complex with two 2-bromobenzoate (BB), two diethylnicotinamide (DENA) ligands and two water molecules, was undertaken in order to determine the properties of the ligands and also to compare the results obtained with those reported previously.

Compound (I) is a monomeric complex, with the Zn atom on a centre of symmetry. It contains two BB, two DENA ligands and two water molecules (Fig. 1). All ligands are monodentate. The four O atoms (O1, O4, and the symmetry-related atoms, O1', O4') in the equatorial plane around the Zn atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two N atoms of the DENA ligands (N1, N1') in the axial positions (Table 1 and Fig. 1).

The near equality of the C1—O1 [1.263 (2) Å] and C1—O2 [1.240 (2) Å] bonds in the carboxylate group indicates a delocalized bonding arrangement, rather than localized single and double bonds, and may be compared with the corresponding distances: 1.256 (6) and 1.245 (6) Å in [Mn(DENA)2(C7H4ClO2)2(H2O)2] (Hökelek et al., 2008), 1.265 (6) and 1.275 (6) Å in [Mn(C9H10NO2)2(H2O)4].2(H2O) (Hökelek & Necefoğlu, 2007), 1.260 (4) and 1.252 (4) Å in [Zn(DENA)2(C7H4FO2)2(H2O)2] (Hökelek et al., 2007), 1.259 (9) and 1.273 (9) Å in Cu2(DENA)2(C6H5COO)4 (Hökelek et al., 1995), 1.279 (4) and 1.246 (4) Å in [Zn2(DENA)2(C7H5O3)4].2H2O (Hökelek & Necefoğlu, 1996), 1.251 (6) and 1.254 (7) Å in [Co(DENA)2(C7H5O3)2(H2O)2] (Hökelek & Necefoğlu, 1997) and 1.278 (3) and 1.246 (3) Å in [Cu(DENA)2(C7H4NO4)2(H2O)2] (Hökelek et al., 1997). In (I), the average Zn—O bond length is 2.0935 (12) Å and the Zn atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by 0.332 (1) Å. The dihedral angle between the planar carboxylate group and the benzene ring A (C2—C7) is 85.51 (12)°, while that between rings A and B (N1/C8—C12) is 44.07 (6)°.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 2) link the molecules into infinite chains, in which they may be effective in the stabilization of the structure.

Experimental

The title compound was prepared by the reaction of ZnSO4.H2O (0.89 g, 5 mmol) in H2O (20 ml) and DENA (1.78 g, 10 mmol) in H2O (20 ml) with sodium 2-bromobenzoate (2.23 g, 10 mmol) in H2O (50 ml). The mixture was filtered and set aside to crystallize at ambient temperature for 3 d, giving colorless single crystals.

Refinement

H atoms of water molecule were located in difference Fourier maps and refined isotropically, with restrains of O4—H41 = 0.885 (16) and O4—H42 = 0.869 (15) Å and H41—O4—H42 = 106 (2)°. The remaining H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å, for aromatic, methylene and methyl H atoms and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are generated by the symmetry operator (1 - x, -y, -z).

Crystal data

[Zn(C7H4BrO2)2(C10H14N2O)2(H2O)2]F(000) = 872
Mr = 857.91Dx = 1.555 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8223 reflections
a = 13.0037 (2) Åθ = 2.5–28.3°
b = 10.3387 (2) ŵ = 2.91 mm1
c = 14.9365 (3) ÅT = 100 K
β = 114.180 (1)°Block, colorless
V = 1831.90 (6) Å30.40 × 0.30 × 0.23 mm
Z = 2

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer4566 independent reflections
Radiation source: fine-focus sealed tube3769 reflections with I > 2σ(I)
graphiteRint = 0.072
[var phi] and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −17→17
Tmin = 0.368, Tmax = 0.517k = −13→12
16722 measured reflectionsl = −15→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.0392P)2] where P = (Fo2 + 2Fc2)/3
4566 reflections(Δ/σ)max < 0.001
232 parametersΔρmax = 1.13 e Å3
3 restraintsΔρmin = −0.53 e Å3

Special details

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)

xyzUiso*/Ueq
Zn10.50000.00000.00000.00901 (8)
Br10.179310 (15)0.14083 (2)0.071591 (15)0.02340 (7)
O10.46937 (9)0.05066 (12)0.12022 (9)0.0132 (3)
O20.36846 (12)−0.11814 (12)0.13299 (11)0.0250 (3)
H410.609 (2)0.2335 (18)0.0563 (19)0.054*
H420.621 (2)0.165 (2)−0.0200 (14)0.051 (8)*
O30.93267 (10)−0.11602 (12)0.39616 (9)0.0145 (3)
O40.61756 (10)0.15513 (11)0.03656 (10)0.0124 (3)
N10.64061 (11)−0.12404 (13)0.09229 (11)0.0112 (3)
N20.98312 (12)0.00393 (14)0.29399 (11)0.0144 (3)
C10.40861 (14)−0.00793 (16)0.15495 (13)0.0126 (4)
C20.38508 (14)0.06826 (17)0.23084 (14)0.0136 (4)
C30.46126 (15)0.06990 (19)0.32819 (14)0.0195 (4)
H30.52550.01850.34820.023*
C40.44314 (17)0.14731 (19)0.39657 (16)0.0239 (5)
H40.49460.14680.46190.029*
C50.34836 (17)0.22509 (19)0.36715 (15)0.0239 (4)
H50.33750.27890.41240.029*
C60.26950 (16)0.22321 (19)0.27050 (15)0.0221 (4)
H60.20500.27420.25070.026*
C70.28856 (15)0.14373 (17)0.20386 (15)0.0166 (4)
C80.64246 (14)−0.25181 (17)0.07850 (14)0.0136 (4)
H80.5822−0.28930.02690.016*
C90.73019 (14)−0.33078 (18)0.13771 (14)0.0145 (4)
H90.7280−0.41930.12600.017*
C100.82084 (13)−0.27652 (17)0.21415 (13)0.0129 (4)
H100.8799−0.32760.25590.016*
C110.82133 (14)−0.14260 (16)0.22691 (13)0.0118 (4)
C120.72970 (13)−0.07125 (17)0.16538 (13)0.0120 (3)
H120.72990.01760.17520.014*
C130.91743 (13)−0.08274 (16)0.31181 (13)0.0113 (3)
C141.08066 (14)0.05572 (17)0.37778 (14)0.0157 (4)
H14A1.06300.05980.43480.019*
H14B1.09630.14290.36290.019*
C151.18465 (15)−0.0281 (2)0.40103 (15)0.0227 (4)
H15A1.24660.00730.45640.034*
H15B1.2035−0.03020.34520.034*
H15C1.1694−0.11440.41610.034*
C160.97478 (16)0.0395 (2)0.19646 (15)0.0239 (4)
H16A0.9254−0.02130.14870.029*
H16B1.04880.03270.19560.029*
C170.93007 (18)0.1756 (2)0.16644 (18)0.0343 (6)
H17A0.93270.19670.10480.051*
H17B0.97560.23590.21560.051*
H17C0.85360.18040.15990.051*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.00857 (13)0.01000 (15)0.00909 (15)−0.00008 (10)0.00427 (11)−0.00017 (11)
Br10.02151 (11)0.02979 (13)0.01957 (12)0.00542 (8)0.00908 (9)0.00255 (8)
O10.0148 (6)0.0149 (6)0.0135 (6)−0.0024 (5)0.0094 (5)−0.0013 (5)
O20.0432 (9)0.0140 (7)0.0321 (9)−0.0092 (6)0.0300 (7)−0.0064 (6)
O30.0162 (6)0.0137 (6)0.0112 (7)−0.0013 (5)0.0031 (5)0.0008 (5)
O40.0138 (6)0.0103 (6)0.0138 (7)−0.0008 (5)0.0064 (5)−0.0003 (5)
N10.0114 (7)0.0109 (7)0.0119 (8)0.0006 (5)0.0054 (6)0.0000 (6)
N20.0141 (7)0.0173 (8)0.0114 (8)−0.0032 (6)0.0048 (6)0.0002 (6)
C10.0138 (8)0.0127 (9)0.0131 (9)0.0033 (6)0.0074 (7)0.0011 (7)
C20.0171 (8)0.0109 (9)0.0183 (9)−0.0041 (7)0.0128 (7)−0.0020 (7)
C30.0174 (9)0.0224 (11)0.0205 (10)−0.0018 (7)0.0098 (8)−0.0032 (8)
C40.0260 (10)0.0318 (12)0.0173 (10)−0.0096 (8)0.0123 (9)−0.0067 (9)
C50.0349 (11)0.0232 (11)0.0243 (11)−0.0068 (8)0.0229 (9)−0.0092 (9)
C60.0267 (10)0.0206 (10)0.0276 (11)0.0011 (8)0.0200 (9)−0.0029 (9)
C70.0191 (9)0.0187 (10)0.0149 (9)−0.0017 (7)0.0102 (8)0.0000 (8)
C80.0114 (8)0.0157 (9)0.0135 (9)−0.0022 (6)0.0050 (7)−0.0013 (7)
C90.0171 (8)0.0099 (8)0.0172 (10)0.0005 (7)0.0076 (7)0.0000 (7)
C100.0125 (8)0.0143 (9)0.0123 (9)0.0026 (6)0.0054 (7)0.0023 (7)
C110.0119 (8)0.0138 (9)0.0107 (9)−0.0016 (6)0.0056 (7)−0.0002 (7)
C120.0142 (8)0.0114 (9)0.0114 (9)−0.0001 (6)0.0063 (7)−0.0002 (7)
C130.0097 (8)0.0090 (8)0.0132 (9)0.0033 (6)0.0026 (7)0.0006 (7)
C140.0166 (8)0.0152 (9)0.0135 (9)−0.0051 (7)0.0043 (7)−0.0023 (8)
C150.0175 (9)0.0282 (11)0.0213 (11)−0.0017 (8)0.0069 (8)0.0031 (9)
C160.0200 (9)0.0365 (12)0.0147 (10)−0.0114 (8)0.0066 (8)0.0017 (9)
C170.0270 (11)0.0413 (14)0.0281 (13)−0.0069 (10)0.0046 (10)0.0191 (11)

Geometric parameters (Å, °)

Zn1—O1i2.0600 (12)C6—H60.9300
Zn1—O12.0600 (12)C7—C21.390 (2)
Zn1—O42.1269 (12)C7—C61.389 (3)
Zn1—N12.1962 (14)C8—C91.387 (2)
Zn1—O4i2.1269 (12)C8—H80.9300
Zn1—N1i2.1962 (14)C9—H90.9300
Br1—C71.903 (2)C10—C91.380 (2)
O1—C11.263 (2)C10—H100.9300
O2—C11.240 (2)C11—C101.397 (2)
O3—C131.241 (2)C11—C121.383 (2)
O4—Zn12.1269 (12)C11—C131.502 (2)
O4—H410.885 (16)C12—H120.9300
O4—H420.869 (15)C13—N21.338 (2)
N1—Zn12.1962 (14)C14—C151.522 (2)
N1—C81.339 (2)C14—H14A0.9700
N1—C121.340 (2)C14—H14B0.9700
N2—C141.470 (2)C15—H15A0.9600
N2—C161.463 (2)C15—H15B0.9600
C2—C11.511 (2)C15—H15C0.9600
C2—C31.384 (3)C16—C171.518 (3)
C3—H30.9300C16—H16A0.9700
C4—C31.391 (3)C16—H16B0.9700
C4—C51.384 (3)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C5—H50.9300C17—H17C0.9600
C6—C51.387 (3)
O1i—Zn1—O1180.00 (5)C6—C7—Br1118.47 (14)
O1i—Zn1—O4i87.69 (5)C6—C7—C2121.96 (19)
O1—Zn1—O4i92.31 (5)N1—C8—C9123.00 (16)
O1i—Zn1—O492.31 (5)N1—C8—H8118.5
O1—Zn1—O487.69 (5)C9—C8—H8118.5
O4i—Zn1—O4180.00 (7)C8—C9—H9120.4
O1i—Zn1—N1i90.56 (5)C10—C9—C8119.27 (17)
O1—Zn1—N1i89.44 (5)C10—C9—H9120.4
O1i—Zn1—N189.44 (5)C9—C10—C11118.05 (16)
O1—Zn1—N190.56 (5)C9—C10—H10121.0
O4i—Zn1—N1i87.31 (5)C11—C10—H10121.0
O4—Zn1—N1i92.69 (5)C10—C11—C13118.64 (15)
O4i—Zn1—N192.69 (5)C12—C11—C10118.91 (16)
O4—Zn1—N187.31 (5)C12—C11—C13122.28 (15)
N1i—Zn1—N1180.00 (14)N1—C12—C11123.12 (16)
C1—O1—Zn1127.79 (11)N1—C12—H12118.4
Zn1—O4—H41126.9 (17)C11—C12—H12118.4
Zn1—O4—H4298.8 (17)O3—C13—N2122.56 (16)
H42—O4—H41106 (2)O3—C13—C11118.34 (15)
C8—N1—Zn1122.85 (11)N2—C13—C11119.10 (16)
C8—N1—C12117.59 (15)N2—C14—C15111.29 (15)
C12—N1—Zn1119.56 (11)N2—C14—H14A109.4
C13—N2—C14118.24 (15)N2—C14—H14B109.4
C13—N2—C16125.02 (15)C15—C14—H14A109.4
C16—N2—C14116.24 (14)C15—C14—H14B109.4
O1—C1—C2114.26 (15)H14A—C14—H14B108.0
O2—C1—O1126.75 (16)C14—C15—H15A109.5
O2—C1—C2118.99 (15)C14—C15—H15B109.5
C3—C2—C1121.12 (16)C14—C15—H15C109.5
C3—C2—C7118.06 (17)H15A—C15—H15B109.5
C7—C2—C1120.76 (17)H15A—C15—H15C109.5
C2—C3—C4120.98 (18)H15B—C15—H15C109.5
C2—C3—H3119.5N2—C16—C17112.98 (18)
C4—C3—H3119.5N2—C16—H16A109.0
C3—C4—H4120.1N2—C16—H16B109.0
C5—C4—C3119.8 (2)C17—C16—H16A109.0
C5—C4—H4120.1C17—C16—H16B109.0
C4—C5—C6120.33 (18)H16A—C16—H16B107.8
C4—C5—H5119.8C16—C17—H17A109.5
C6—C5—H5119.8C16—C17—H17B109.5
C5—C6—C7118.77 (18)C16—C17—H17C109.5
C5—C6—H6120.6H17A—C17—H17B109.5
C7—C6—H6120.6H17A—C17—H17C109.5
C2—C7—Br1119.57 (14)H17B—C17—H17C109.5
O4i—Zn1—O1—C15.89 (14)C1—C2—C3—C4175.41 (16)
O4—Zn1—O1—C1−174.11 (14)C7—C2—C3—C4−1.6 (3)
N1i—Zn1—O1—C193.18 (14)C5—C4—C3—C2−0.7 (3)
N1—Zn1—O1—C1−86.82 (14)C3—C4—C5—C62.1 (3)
Zn1—O1—C1—O211.8 (3)C7—C6—C5—C4−1.1 (3)
Zn1—O1—C1—C2−168.33 (11)Br1—C7—C2—C14.8 (2)
C8—N1—Zn1—O1i−61.43 (14)Br1—C7—C2—C3−178.23 (13)
C8—N1—Zn1—O1118.57 (14)C6—C7—C2—C1−174.44 (16)
C8—N1—Zn1—O4i26.23 (14)C6—C7—C2—C32.6 (3)
C8—N1—Zn1—O4−153.77 (14)Br1—C7—C6—C5179.54 (14)
C12—N1—Zn1—O1i117.92 (13)C2—C7—C6—C5−1.2 (3)
C12—N1—Zn1—O1−62.08 (13)N1—C8—C9—C10−0.6 (3)
C12—N1—Zn1—O4i−154.42 (13)C11—C10—C9—C8−1.6 (3)
C12—N1—Zn1—O425.58 (13)C12—C11—C10—C92.5 (3)
Zn1—N1—C8—C9−178.82 (13)C13—C11—C10—C9177.93 (16)
C12—N1—C8—C91.8 (3)C10—C11—C12—N1−1.3 (3)
Zn1—N1—C12—C11179.78 (13)C13—C11—C12—N1−176.57 (16)
C8—N1—C12—C11−0.8 (2)C10—C11—C13—O3−61.1 (2)
C13—N2—C14—C1588.7 (2)C10—C11—C13—N2118.94 (18)
C16—N2—C14—C15−83.6 (2)C12—C11—C13—O3114.20 (19)
C13—N2—C16—C17109.9 (2)C12—C11—C13—N2−65.8 (2)
C14—N2—C16—C17−78.4 (2)O3—C13—N2—C143.5 (2)
C3—C2—C1—O1−83.7 (2)O3—C13—N2—C16175.04 (17)
C3—C2—C1—O296.2 (2)C11—C13—N2—C14−176.49 (14)
C7—C2—C1—O193.2 (2)C11—C13—N2—C16−4.9 (3)
C7—C2—C1—O2−86.9 (2)

Symmetry codes: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H41···O3ii0.88 (2)1.88 (2)2.7518 (18)168 (3)
O4—H42···O2i0.87 (2)1.81 (2)2.640 (2)158 (2)

Symmetry codes: (ii) −x+3/2, y+1/2, −z+1/2; (i) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2502).

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