cis-Bis(butyl­amine-κN)bis­[sulfa­diazine(1−)-κ2 N,N′]copper(II) penta­hydrate

Hümeyra Paşaoğlu; Gökhan Kaştaş; Zerrin Heren; Orhan Büyükgüngör

doi:10.1107/S1600536808026457

. 2008 Aug 23;64(Pt 9):m1192. doi: 10.1107/S1600536808026457

cis-Bis(butylamine-κN)bis[sulfadiazine(1−)-κ² N,N′]copper(II) pentahydrate

Hümeyra Paşaoğlu ^a, Gökhan Kaştaş ^a,^*, Zerrin Heren ^b, Orhan Büyükgüngör ^a

PMCID: PMC2960652 PMID: 21201631

Abstract

In the title compound {systematic name: cis-bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato-κ² N,N′]bis(butylamine-κN)copper(II) pentahydrate}, [Cu(C₁₀H₉N₄O₂S)₂(C₄H₁₁N)₂]·5H₂O or [Cu(sdz)₂(ba)₂]·5H₂O [ba is butylamine and sdz = sulfadiazine(1−)], the copper(II) cation is six-coordinated by four N atoms of two sulfadiazine ligands and two N atoms of butylamine ligands. The copper(II) ion and one of the water molecules lie on twofold rotation axes. One of the butyl groups is disordered over two sites, with occupancies of 0.395 (8) and 0.605 (8). The geometry around the S atom is distorted tetrahedral. The crystal structure involves intermolecular N—H⋯N and N—H⋯O hydrogen bonds. N—H⋯N hydrogen bonds between sdz ligands lead to a sheet structure parallel to the ab plane.

Related literature

For related structures, see: Heren et al. (2006 ▶); Chung et al. (1975 ▶).

Experimental

Crystal data

[Cu(C₁₀H₉N₄O₂S)₂(C₄H₁₁N)₂]·5H₂O
M _r = 790.04
Orthorhombic,
a = 22.623 (6) Å
b = 10.342 (5) Å
c = 16.250 (6) Å
V = 3802 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 296 K
0.34 × 0.21 × 0.19 mm

Data collection

Stoe IPDS2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.821, T _max = 0.899
57960 measured reflections
4235 independent reflections
2098 reflections with I > 2σ(I)
R _int = 0.085

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.141
S = 0.90
4235 reflections
234 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026457/cf2216sup1.cif

e-64-m1192-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026457/cf2216Isup2.hkl

e-64-m1192-Isup2.hkl^{(179.7KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯N2ⁱ	0.86	2.53	3.359 (5)	162
N4—H4A⋯O5ⁱⁱ	0.90	2.45	3.337 (6)	171
N4—H4B⋯O4ⁱⁱⁱ	0.90	2.25	3.119 (6)	161
N5—H5B⋯O5^iv	0.86	2.26	3.113 (5)	170

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors thank the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

In the title complex (I), the copper(II) ion is six-coordinated by four N atoms of sulfadiazine ligands and two N atoms of butylammonium ligands. The copper(II) ion and one of the water molecules lie on twofold rotation axes. It is found that the Cu–N_sdz and Cu–N_ba bond distances are nearly equal. The bond angles around the S atom correspond to a distorted tetrahedral geometry. The C4–N5 bond distance and the torsion angle C1–S1–N1–C7 are comparable to those observed in related structures (Heren et al., 2006; Chung et al., 1975). One of the butyl groups is disordered over two sites with occupancies of 0.395 (8):0.605 (8) (see Fig. 1).

The packing of (I) is stabilized by intermolecular N—H···N and N—H···O hydrogen bonds (Table 1). The N—H···N hydrogen bond takes place between sdz ligands and it is seen that these hydrogen bonds generate a sheet structure parallel to the ab plane (Fig. 2). The H atoms of water molecules could not be located from a Fourier map. However, it is possible to see that water molecules are involved in hydrogen bonds with sdz and ba ligands on the basis of interatomic distances.

Experimental

A solution of butylamine (2 mmol) in ethanol (20 ml) was added dropwise with stirring to a solution of Cu(II) sulfadiazine (1 mmol) in methanol (40 ml). The solution was heated and stirred for 3 h at 343 K and then the mixture was cooled to room temperature. The blue crystals were filtered off, washed with cold distilled water and acetone, and dried in vacuo. Analysis calculated: C 42.62, H 5.84, N 17.76%; found: C 43.08, H 5.72, N 18.25%.