[4-(2-Amino­ethyl)piperazin-1-ium]trichloridocopper(II) monohydrate

Ikram, B.; Fatma, Z.

doi:10.1107/S1600536809046121

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1539

doi:10.1107/S1600536809046121

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[4-(2-Aminoethyl)piperazin-1-ium]trichloridocopper(II) monohydrate

Baccar Ikram ^a and Zouari Fatma ^a ^*

^aLaboratoire de Sciences de Matériaux et d'Environnement, Faculté des Sciences de SFAX, BP 802, 3018 SFAX, Tunisia
^*Correspondence e-mail: fatmazouari2003@yahoo.fr

(Received 16 October 2009; accepted 2 November 2009; online 7 November 2009)

In the title compound, [CuCl₃(C₆H₁₆N₃)]·H₂O, the copper(II) ion is five-coordinated by two N atoms from the bidentate 4-(2-aminoethyl)piperazin-1-ium cation and three chloride ions in a distorted square-pyramidal environment. Intermolecular N—H⋯Cl and O—H⋯Cl hydrogen bonds build up an intricate three-dimensional network.

Related literature

For background information on polydentate ligands with nitrogen donor atoms, see: Riggio et al. (2001 ); Xiang et al. (2007 ); Gokhale et al. (2001 ). The copper(II) ion, owing to the 'plasticity' of the coordination sphere, forms complexes of coordination number 4–6, with a variety of irregular geometries, see: Fujisawa et al. (2008 ).

Experimental

Crystal data

[CuCl₃(C₆H₁₆N₃)]·H₂O
M_r = 318.13
Monoclinic, P 2₁ /n
a = 9.0540 (6) Å
b = 14.8840 (13) Å
c = 9.1040 (2) Å
β = 94.019 (5)°
V = 1223.84 (14) Å³
Z = 4
Mo Kα radiation
μ = 2.41 mm⁻¹
T = 293 K
0.35 × 0.21 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker et al., 1998 ) T_min = 0.541, T_max = 0.685
21677 measured reflections
4410 independent reflections
3444 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.102
S = 1.19
4410 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯Cl2	0.97	2.21	3.154 (4)	164
O1W—H2⋯Cl1ⁱ	0.97	2.40	3.239 (4)	144
N1—H1A⋯Cl1ⁱⁱ	0.90	2.63	3.395 (2)	143
N1—H1B⋯Cl3ⁱⁱⁱ	0.90	2.43	3.302 (2)	162
N3—H3A⋯Cl2^iv	0.90	2.38	3.204 (2)	152
N3—H3B⋯Cl3^v	0.90	2.24	3.131 (2)	169
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046121/dn2503sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046121/dn2503Isup2.hkl

checkCIF report

Comment top

Polydentate ligands with nitrogen donor atoms are largely employed in mimicking the environnement of the copper in models of biological interest, whose coordination environment is provided by nitrogen atoms of the ligand, plus one or more exogeneous ligands (Riggio et al., 2001; Xiang et al., 2007; Gokhale et al., 2001). It is of current interest to correlate the flexibility of the model ligand and its sterical hindrance with the geometry of the complex. The copper(II) ion, owing to the well known 'plasticity' of the coordination sphere, forms complexes of co-ordination number 4–6, with a variety of irregular geometries (Fujisawa et al., 2008), both the anions and the solvent playing often a vital role on the stoichiometry and stereochemistry of the complexes (Xiang et al., 2007). In this paper, we report on the synthesis and the crystal structure determinationof N2 bidentate copper(II) complex 1-(2-ammoniumethyl) piperazinium trichlorocuprate(II)monohydrate (Scheme).

The structure of the title compound consists of discrete copper(II) neutral complexes with the metal atom five-coordinated to two N atoms from the bidentate 1-(2-aminoethyl) piperazine and three chlorine atoms in a square pyramidal environment (Fig. 1). The square plane is defined by two N atoms from organic cation and the more strongly bonded Cl1 and Cl2 chlorine, the apical position is occupied by the Cl3 chlorine atom. The Cu—Cl3 distance 2.6095 (8)Å is significantly longer than the normal bond length, which reflects the weak axial interactions as expected for Jahn-Teller distorted copper (II) complexes. The value of structural parameter τ is 0.17, showing a distorted square pyramidal structure, where τ is defined as τ = (α-β)/60°, where α and β are the largest angles (α> β) around a five coordinated metal center (τ is equal to 0 for an ideal square pyramidal geometry).

The intermolecular hydrogen bonds, N—H···Cl and O—H···Cl, build up an intricated three dimensionnal network (Table 1, Fig. 2).

Related literature top

For background information on polydentate ligands with nitrogen donor atoms, see: Riggio et al. (2001); Xiang et al. (2007); Gokhale et al. (2001). For the copper(II) ion, see: Fujisawa et al. (2008).

Experimental top

To a solution of 1-(2-aminoethyl) piperazine compound (10 mmol) in chlorhydric acid (35 ml) was added a solution of CuCl₂.2H₂O(10 mmol) in acetone (15 ml). After a few days to 3 weeks, the product separates as crystals, which were isolated by filtration and dried in air. The new compound show satisfactory elemental analyses.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probabilit level. H atoms are represented as small spheres of arbitrary radii. H bond is shown as dashed line.
	Fig. 2. Partial packing view showing the intricated N—H···Cl and O—H···Cl network. H atoms not involved in hydrogen bondings have been omitted for clarity. H bonds are shown as dashed lines. [Symmetry code: (i) x - 1, y, z]

[4-(2-Aminoethyl)piperazin-1-ium]trichloridocopper(II) monohydrate top

Crystal data top

[CuCl₃(C₆H₁₆N₃)]·H₂O	F(000) = 652
M_r = 318.13	D_x = 1.727 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 455 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.0540 (6) Å	Cell parameters from 4604 reflections
b = 14.8840 (13) Å	θ = 3.1–33.0°
c = 9.1040 (2) Å	µ = 2.41 mm⁻¹
β = 94.019 (5)°	T = 293 K
V = 1223.84 (14) Å³	Prism, colourless
Z = 4	0.35 × 0.21 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4410 independent reflections
Radiation source: fine-focus sealed tube	3444 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 33.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→13
T_min = 0.541, T_max = 0.685	k = −20→22
21677 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0308P)² + 1.5885P] where P = (F_o² + 2F_c²)/3
4410 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

[CuCl₃(C₆H₁₆N₃)]·H₂O	V = 1223.84 (14) Å³
M_r = 318.13	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0540 (6) Å	µ = 2.41 mm⁻¹
b = 14.8840 (13) Å	T = 293 K
c = 9.1040 (2) Å	0.35 × 0.21 × 0.15 mm
β = 94.019 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4410 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3444 reflections with I > 2σ(I)
T_min = 0.541, T_max = 0.685	R_int = 0.032
21677 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.19	Δρ_max = 0.75 e Å⁻³
4410 reflections	Δρ_min = −0.73 e Å⁻³
127 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
Cu1	0.52502 (3)	0.275723 (19)	0.26008 (3)	0.02535 (8)
Cl1	0.69453 (8)	0.34628 (4)	0.12625 (7)	0.03484 (14)
Cl2	0.35774 (8)	0.39523 (4)	0.23087 (8)	0.03722 (15)
Cl3	0.60236 (8)	0.32232 (5)	0.53095 (8)	0.04205 (17)
N1	0.3558 (2)	0.19697 (14)	0.3082 (2)	0.0301 (4)
H1A	0.3237	0.2139	0.3954	0.036*
H1B	0.2807	0.2044	0.2391	0.036*
N2	0.6475 (2)	0.15459 (12)	0.2700 (2)	0.0238 (4)
N3	0.8947 (3)	0.04353 (15)	0.1831 (3)	0.0373 (5)
H3A	0.9412	−0.0099	0.1866	0.045*
H3B	0.9465	0.0810	0.1285	0.045*
C1	0.3973 (3)	0.10108 (17)	0.3155 (3)	0.0339 (5)
H11	0.3787	0.0734	0.2196	0.041*
H12	0.3389	0.0699	0.3850	0.041*
C2	0.5603 (3)	0.09485 (16)	0.3645 (3)	0.0305 (5)
H21	0.5758	0.1131	0.4667	0.037*
H22	0.5936	0.0332	0.3565	0.037*
C3	0.8026 (3)	0.16627 (16)	0.3349 (3)	0.0308 (5)
H31	0.7998	0.1878	0.4352	0.037*
H32	0.8515	0.2117	0.2792	0.037*
C4	0.8927 (3)	0.08025 (18)	0.3355 (3)	0.0353 (6)
H41	0.9932	0.0923	0.3744	0.042*
H42	0.8500	0.0362	0.3987	0.042*
C5	0.7427 (3)	0.03183 (17)	0.1101 (3)	0.0344 (6)
H51	0.6915	−0.0157	0.1589	0.041*
H52	0.7497	0.0147	0.0081	0.041*
C6	0.6557 (3)	0.11889 (17)	0.1175 (3)	0.0297 (5)
H61	0.7012	0.1639	0.0583	0.036*
H62	0.5559	0.1089	0.0748	0.036*
O1W	0.0185 (4)	0.3850 (3)	0.2878 (5)	0.0994 (12)
H1	0.1193	0.3767	0.2606	0.149*
H2	−0.0540	0.3497	0.2295	0.149*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02915 (15)	0.02000 (13)	0.02711 (15)	0.00087 (10)	0.00348 (10)	0.00021 (10)
Cl1	0.0433 (4)	0.0240 (3)	0.0390 (3)	0.0025 (2)	0.0153 (3)	0.0055 (2)
Cl2	0.0342 (3)	0.0270 (3)	0.0499 (4)	0.0043 (2)	−0.0007 (3)	−0.0008 (3)
Cl3	0.0426 (4)	0.0499 (4)	0.0325 (3)	0.0124 (3)	−0.0058 (3)	−0.0154 (3)
N1	0.0291 (10)	0.0298 (10)	0.0315 (10)	−0.0012 (8)	0.0021 (8)	0.0019 (8)
N2	0.0308 (10)	0.0188 (8)	0.0220 (8)	0.0011 (7)	0.0029 (7)	0.0017 (6)
N3	0.0422 (13)	0.0230 (9)	0.0489 (14)	0.0071 (9)	0.0190 (11)	0.0034 (9)
C1	0.0362 (13)	0.0263 (11)	0.0402 (14)	−0.0064 (10)	0.0097 (11)	0.0001 (10)
C2	0.0397 (14)	0.0253 (10)	0.0271 (11)	0.0018 (9)	0.0071 (10)	0.0056 (9)
C3	0.0340 (13)	0.0228 (10)	0.0352 (13)	0.0000 (9)	−0.0007 (10)	−0.0031 (9)
C4	0.0335 (13)	0.0278 (11)	0.0440 (15)	0.0056 (10)	−0.0023 (11)	0.0010 (10)
C5	0.0496 (16)	0.0239 (11)	0.0311 (12)	−0.0004 (10)	0.0128 (11)	−0.0036 (9)
C6	0.0418 (14)	0.0271 (11)	0.0204 (10)	0.0006 (10)	0.0035 (9)	−0.0004 (8)
O1W	0.072 (2)	0.120 (3)	0.105 (3)	−0.002 (2)	0.002 (2)	−0.018 (2)

Geometric parameters (Å, º) top

Cu1—N1	2.002 (2)	C1—H11	0.9700
Cu1—N2	2.1153 (19)	C1—H12	0.9700
Cu1—Cl1	2.2814 (7)	C2—H21	0.9700
Cu1—Cl2	2.3392 (7)	C2—H22	0.9700
Cu1—Cl3	2.6097 (7)	C3—C4	1.518 (4)
N1—C1	1.476 (3)	C3—H31	0.9700
N1—H1A	0.9000	C3—H32	0.9700
N1—H1B	0.9000	C4—H41	0.9700
N2—C6	1.493 (3)	C4—H42	0.9700
N2—C3	1.495 (3)	C5—C6	1.520 (4)
N2—C2	1.500 (3)	C5—H51	0.9700
N3—C4	1.493 (4)	C5—H52	0.9700
N3—C5	1.496 (4)	C6—H61	0.9700
N3—H3A	0.9000	C6—H62	0.9700
N3—H3B	0.9000	O1W—H1	0.9701
C1—C2	1.514 (4)	O1W—H2	0.9694

N1—Cu1—N2	84.19 (8)	H11—C1—H12	108.4
N1—Cu1—Cl1	160.09 (7)	N2—C2—C1	109.6 (2)
N2—Cu1—Cl1	92.56 (6)	N2—C2—H21	109.7
N1—Cu1—Cl2	88.32 (7)	C1—C2—H21	109.7
N2—Cu1—Cl2	170.50 (6)	N2—C2—H22	109.7
Cl1—Cu1—Cl2	92.50 (3)	C1—C2—H22	109.7
N1—Cu1—Cl3	96.18 (7)	H21—C2—H22	108.2
N2—Cu1—Cl3	94.65 (6)	N2—C3—C4	113.1 (2)
Cl1—Cu1—Cl3	103.67 (3)	N2—C3—H31	109.0
Cl2—Cu1—Cl3	91.95 (3)	C4—C3—H31	109.0
C1—N1—Cu1	112.31 (16)	N2—C3—H32	109.0
C1—N1—H1A	109.1	C4—C3—H32	109.0
Cu1—N1—H1A	109.1	H31—C3—H32	107.8
C1—N1—H1B	109.1	N3—C4—C3	110.3 (2)
Cu1—N1—H1B	109.1	N3—C4—H41	109.6
H1A—N1—H1B	107.9	C3—C4—H41	109.6
C6—N2—C3	107.62 (19)	N3—C4—H42	109.6
C6—N2—C2	112.64 (19)	C3—C4—H42	109.6
C3—N2—C2	111.08 (19)	H41—C4—H42	108.1
C6—N2—Cu1	108.90 (14)	N3—C5—C6	110.1 (2)
C3—N2—Cu1	113.13 (14)	N3—C5—H51	109.6
C2—N2—Cu1	103.53 (14)	C6—C5—H51	109.6
C4—N3—C5	112.6 (2)	N3—C5—H52	109.6
C4—N3—H3A	109.1	C6—C5—H52	109.6
C5—N3—H3A	109.1	H51—C5—H52	108.1
C4—N3—H3B	109.1	N2—C6—C5	113.8 (2)
C5—N3—H3B	109.1	N2—C6—H61	108.8
H3A—N3—H3B	107.8	C5—C6—H61	108.8
N1—C1—C2	108.2 (2)	N2—C6—H62	108.8
N1—C1—H11	110.1	C5—C6—H62	108.8
C2—C1—H11	110.1	H61—C6—H62	107.7
N1—C1—H12	110.1	H1—O1W—H2	113.8
C2—C1—H12	110.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···Cl2	0.97	2.21	3.154 (4)	164
O1W—H2···Cl1ⁱ	0.97	2.40	3.239 (4)	144
N1—H1A···Cl1ⁱⁱ	0.90	2.63	3.395 (2)	143
N1—H1B···Cl3ⁱⁱⁱ	0.90	2.43	3.302 (2)	162
N3—H3A···Cl2^iv	0.90	2.38	3.204 (2)	152
N3—H3B···Cl3^v	0.90	2.24	3.131 (2)	169

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

Experimental details

Crystal data
Chemical formula	[CuCl₃(C₆H₁₆N₃)]·H₂O
M_r	318.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.0540 (6), 14.8840 (13), 9.1040 (2)
β (°)	94.019 (5)
V (Å³)	1223.84 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.41
Crystal size (mm)	0.35 × 0.21 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.541, 0.685
No. of measured, independent and observed [I > 2σ(I)] reflections	21677, 4410, 3444
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.766

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.19
No. of reflections	4410
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.73

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···Cl2	0.97	2.21	3.154 (4)	163.6
O1W—H2···Cl1ⁱ	0.97	2.40	3.239 (4)	144.4
N1—H1A···Cl1ⁱⁱ	0.90	2.63	3.395 (2)	142.9
N1—H1B···Cl3ⁱⁱⁱ	0.90	2.43	3.302 (2)	162.0
N3—H3A···Cl2^iv	0.90	2.38	3.204 (2)	151.7
N3—H3B···Cl3^v	0.90	2.24	3.131 (2)	169.4

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

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1539

doi:10.1107/S1600536809046121

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