[4,4′-(Ethane-1,2-diyldinitrilo)­bis­(pent-2-en-2-olato)]copper(II) 0.25-hydrate

Aslam, M.; Anis, I.; Afza, N.; Hussain, A.; Ahmed, W.; Arshad, M.N.

doi:10.1107/S1600536812017102

metal-organic compounds

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Volume 68| Part 5| May 2012| Page m670

doi:10.1107/S1600536812017102

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[4,4′-(Ethane-1,2-diyldinitrilo)bis(pent-2-en-2-olato)]copper(II) 0.25-hydrate

Muhammad Aslam,^a ^*‡ Itrat Anis,^b Nighat Afza,^a Ajaz Hussain,^c Waseem Ahmed ^d and Muhammad Nadeem Arshad ^e ^*

^aPakistan Council of Scientific and Industrial Research Laboratories Complex, Karachi 75280, Pakistan, ^bDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, ^cDepartment of Chemistry, GC University, Faisalabad, Pakistan, ^dDepartment of Biochemistry, Federal Urdu University of Arts Science and Technology, Gulshan-e-Iqbal Campus, Karachi, Pakistan, and ^eDepartment of Chemistry, University of Gujrat (Hafiz Hayat campus), Gujrat 50781, Pakistan
^*Correspondence e-mail: maslamchemist@hotmail.com, mnachemist@hotmail.com

(Received 12 April 2012; accepted 18 April 2012; online 25 April 2012)

In the title compound, [Cu(C₁₂H₁₈N₂O₂)]·0.25H₂O, the coordination of the O,N,N′,O′-tetradentate ligand results in a cis-CuN₂O₂ square-planar geometry for the metal ion and the presence of two six-membered and one five-membered chelate rings. The complete complex molecule is close to planar (r.m.s. deviation = 0.047 Å). The uncoordinated water molecule (O-atom site symmetry 2) was modelled as half occupied. In the crystal, C—H⋯O_w and O_w—H⋯O (w = water) hydrogen bonds link the components into layers parallel to ab plane.

Related literature

For background to Schiff bases and their complexes, see: Aslam et al. (2012 ).

Experimental

Crystal data

[Cu(C₁₂H₁₈N₂O₂)]·0.25H₂O
M_r = 290.33
Orthorhombic, P b c n
a = 17.0029 (7) Å
b = 8.0198 (3) Å
c = 19.6532 (7) Å
V = 2679.91 (18) Å³
Z = 8
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 296 K
0.24 × 0.21 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.697, T_max = 0.817
22704 measured reflections
3338 independent reflections
1745 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.190
S = 1.07
3338 reflections
166 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O2	1.897 (4)
Cu1—O1	1.901 (4)
Cu1—N2	1.922 (4)
Cu1—N1	1.926 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1Wⁱ	0.96	2.58	3.466 (9)	154
C6—H6B⋯O1Wⁱ	0.97	2.44	3.303 (11)	149
O1W—H1WA⋯O2	0.79 (2)	2.29 (14)	2.862 (8)	130 (13)
Symmetry code: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812017102/hb6739sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017102/hb6739Isup2.hkl

checkCIF report

Comment top

Herein we report the crystal structure of title compound, (I), which is a Cu complex of schiff base in countinuation of our studies on synthesis and metal complexation of schiff bases (Aslam et al., 2012). The copper metal bonded to the ligand 4,4'-(ethane-1,2-diyldinitrilo)bispent-2-en-2-ol through Cu—O covelant & Cu—N coordinate covelant bonds in such a way that it causes to produce two six membered rings (C2/C3/C4/Cu1/N1/O1) "A" & (C7/C8/C9/Cu1/N2/O2) "B" and a five membered ring (C5/C6/N1/Cu1/N2) "C". All these three rings are almost planer with the r. m. s. deviation of 0.0114 Å, 0.0061 Å and 0.0273 Å respectively. The molecule as a whole is slightly twisted as the five membered ring is oriented at dihedral angle of 2.54 (23)° and 3.34 (23)° with respect to six membered rings "A" and "B". Both of six membered rings are twisted at angle of 3.47 (16)° which showes the slight nonplaner behaviour of the molecule.

Moreover, a half water molecule have also been identified during refinement which links the molecules in two dimensional network through O—H···O and C—H···O interactions along a & b axes (Table. 2, Fig. 2).

Related literature top

For background to Schiff bases and their complexes, see: Aslam et al. (2012).

Experimental top

A methanolic solution of copper (II) chloride dihydrated (1 mol) (5 ml) was slowly added to a methanolic solution of 4-{[2-((1-methyl-3-oxobutylidene)amino)ethyl]imino}-2-pentanone (1 mol) (100 ml) and refluxed with stirring for 45 min. The pH was gradually raised to achieve the suitable pH for the formulation of the complex by the drop wise addition of 1 M NaOH solution. Now the reaction mixture was refluxed with stirring for 90 min. After cooling, the mixture was concentrated to one third under reduced pressure. The concentrated reaction mixture was kept at room temperature and black crystals were obtained after six days. The crystalline product was collected, washed with cooled methanol, recrystallized from ethylacetate and methanol (1:1) mixture and dried to afford the title compound in 73.1% yield. Slow evaporation of a methanol solution afforded dark brown blocks of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with 50% displacement ellipsoids.
	Fig. 2. A view of the unit cell packing showing two dimensional hydrogen bonding network through dashed lines.

[4,4'-(Ethane-1,2-diyldinitrilo)bis(pent-2-en-2-olato)]copper(II) 0.25-hydrate top

Crystal data top

[Cu(C₁₂H₁₈N₂O₂)]·0.25H₂O	F(000) = 1212
M_r = 290.33	D_x = 1.439 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5532 reflections
a = 17.0029 (7) Å	θ = 2.4–25.9°
b = 8.0198 (3) Å	µ = 1.62 mm⁻¹
c = 19.6532 (7) Å	T = 296 K
V = 2679.91 (18) Å³	Block, dark brown
Z = 8	0.24 × 0.21 × 0.13 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3338 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −22→22
T_min = 0.697, T_max = 0.817	k = −8→10
22704 measured reflections	l = −22→26

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0608P)² + 6.2772P] where P = (F_o² + 2F_c²)/3
3338 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.56 e Å⁻³
1 restraint	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Cu(C₁₂H₁₈N₂O₂)]·0.25H₂O	V = 2679.91 (18) Å³
M_r = 290.33	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 17.0029 (7) Å	µ = 1.62 mm⁻¹
b = 8.0198 (3) Å	T = 296 K
c = 19.6532 (7) Å	0.24 × 0.21 × 0.13 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3338 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1745 reflections with I > 2σ(I)
T_min = 0.697, T_max = 0.817	R_int = 0.042
22704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	1 restraint
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.56 e Å⁻³
3338 reflections	Δρ_min = −0.39 e Å⁻³
166 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Cu1	0.28720 (4)	0.12613 (9)	0.19272 (3)	0.0578 (3)
O1	0.3694 (2)	0.1823 (5)	0.13133 (18)	0.0729 (11)
O2	0.3675 (2)	0.0653 (6)	0.25492 (19)	0.0791 (12)
N1	0.2057 (2)	0.2001 (5)	0.1317 (2)	0.0557 (10)
N2	0.2037 (3)	0.0604 (5)	0.2529 (2)	0.0609 (11)
C1	0.4377 (4)	0.2870 (10)	0.0361 (3)	0.096 (2)
H1A	0.4698	0.1885	0.0365	0.144*
H1B	0.4650	0.3758	0.0589	0.144*
H1C	0.4272	0.3189	−0.0101	0.144*
C2	0.3606 (4)	0.2520 (7)	0.0726 (3)	0.0662 (15)
C3	0.2912 (4)	0.2910 (7)	0.0431 (3)	0.0670 (15)
H3	0.2932	0.3401	0.0002	0.080*
C4	0.2160 (3)	0.2638 (6)	0.0715 (3)	0.0596 (13)
C5	0.1275 (4)	0.1746 (10)	0.1597 (4)	0.094 (2)
H5A	0.1025	0.2822	0.1659	0.113*
H5B	0.0963	0.1117	0.1273	0.113*
C6	0.1280 (4)	0.0880 (11)	0.2234 (4)	0.109 (3)
H6A	0.0964	0.1507	0.2555	0.131*
H6B	0.1027	−0.0193	0.2169	0.131*
C7	0.2129 (4)	−0.0013 (8)	0.3139 (3)	0.0741 (17)
C8	0.2866 (5)	−0.0314 (8)	0.3429 (3)	0.084 (2)
H8	0.2871	−0.0793	0.3859	0.100*
C9	0.3573 (5)	0.0023 (9)	0.3145 (3)	0.0825 (18)
C10	0.4323 (5)	−0.0375 (12)	0.3520 (4)	0.126 (3)
H10A	0.4631	0.0622	0.3569	0.189*
H10B	0.4617	−0.1189	0.3269	0.189*
H10C	0.4199	−0.0811	0.3962	0.189*
C11	0.1458 (4)	0.3136 (9)	0.0287 (3)	0.094 (2)
H11A	0.1143	0.3925	0.0534	0.141*
H11B	0.1149	0.2166	0.0186	0.141*
H11C	0.1637	0.3633	−0.0129	0.141*
C12	0.1418 (5)	−0.0453 (10)	0.3561 (4)	0.116 (3)
H12A	0.1105	−0.1259	0.3323	0.174*
H12B	0.1111	0.0533	0.3642	0.174*
H12C	0.1585	−0.0912	0.3988	0.174*
O1W	0.5000	0.2851 (13)	0.2500	0.070 (3)	0.50
H1WA	0.484 (9)	0.205 (9)	0.269 (6)	0.105*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0602 (4)	0.0703 (5)	0.0430 (4)	0.0012 (4)	−0.0011 (3)	−0.0032 (3)
O1	0.054 (2)	0.116 (3)	0.049 (2)	−0.002 (2)	−0.0047 (17)	0.005 (2)
O2	0.071 (2)	0.117 (3)	0.049 (2)	0.011 (2)	−0.0059 (19)	0.006 (2)
N1	0.053 (2)	0.059 (2)	0.056 (2)	0.002 (2)	0.003 (2)	−0.010 (2)
N2	0.068 (3)	0.060 (3)	0.055 (3)	−0.006 (2)	0.004 (2)	−0.008 (2)
C1	0.088 (5)	0.124 (6)	0.075 (4)	−0.022 (5)	0.017 (4)	0.006 (4)
C2	0.069 (4)	0.079 (4)	0.051 (3)	−0.011 (3)	0.007 (3)	−0.006 (3)
C3	0.081 (4)	0.074 (4)	0.047 (3)	−0.002 (3)	−0.004 (3)	0.006 (3)
C4	0.072 (3)	0.052 (3)	0.055 (3)	0.005 (3)	−0.010 (3)	−0.010 (2)
C5	0.064 (4)	0.131 (6)	0.088 (5)	0.002 (4)	0.009 (4)	−0.012 (4)
C6	0.074 (5)	0.156 (8)	0.097 (5)	−0.013 (5)	0.007 (4)	0.009 (5)
C7	0.111 (5)	0.057 (3)	0.055 (3)	−0.013 (4)	0.016 (4)	−0.009 (3)
C8	0.131 (6)	0.075 (4)	0.045 (3)	0.003 (4)	−0.001 (4)	0.004 (3)
C9	0.105 (5)	0.087 (4)	0.055 (4)	0.014 (4)	−0.017 (4)	−0.001 (3)
C10	0.133 (7)	0.167 (8)	0.076 (5)	0.032 (6)	−0.043 (5)	0.014 (5)
C11	0.097 (5)	0.103 (5)	0.082 (4)	0.014 (4)	−0.029 (4)	0.009 (4)
C12	0.156 (7)	0.120 (6)	0.073 (4)	−0.041 (6)	0.037 (5)	−0.003 (4)
O1W	0.033 (5)	0.055 (6)	0.122 (10)	0.000	−0.007 (6)	0.000

Geometric parameters (Å, º) top

Cu1—O2	1.897 (4)	C5—H5A	0.9700
Cu1—O1	1.901 (4)	C5—H5B	0.9700
Cu1—N2	1.922 (4)	C6—H6A	0.9700
Cu1—N1	1.926 (4)	C6—H6B	0.9700
O1—C2	1.291 (6)	C7—C8	1.398 (8)
O2—C9	1.287 (7)	C7—C12	1.509 (9)
N1—C4	1.301 (7)	C8—C9	1.352 (9)
N1—C5	1.454 (7)	C8—H8	0.9300
N2—C7	1.307 (7)	C9—C10	1.506 (9)
N2—C6	1.429 (8)	C10—H10A	0.9600
C1—C2	1.521 (8)	C10—H10B	0.9600
C1—H1A	0.9600	C10—H10C	0.9600
C1—H1B	0.9600	C11—H11A	0.9600
C1—H1C	0.9600	C11—H11B	0.9600
C2—C3	1.351 (7)	C11—H11C	0.9600
C3—C4	1.412 (7)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C11	1.514 (7)	C12—H12C	0.9600
C5—C6	1.431 (10)	O1W—H1WA	0.79 (2)

O2—Cu1—O1	86.59 (16)	H5A—C5—H5B	107.7
O2—Cu1—N2	93.75 (19)	N2—C6—C5	115.8 (6)
O1—Cu1—N2	177.56 (18)	N2—C6—H6A	108.3
O2—Cu1—N1	176.84 (19)	C5—C6—H6A	108.3
O1—Cu1—N1	93.48 (17)	N2—C6—H6B	108.3
N2—Cu1—N1	86.31 (19)	C5—C6—H6B	108.3
C2—O1—Cu1	125.8 (4)	H6A—C6—H6B	107.4
C9—O2—Cu1	126.2 (5)	N2—C7—C8	123.2 (6)
C4—N1—C5	121.5 (5)	N2—C7—C12	119.8 (7)
C4—N1—Cu1	126.2 (4)	C8—C7—C12	117.0 (6)
C5—N1—Cu1	112.3 (4)	C9—C8—C7	126.5 (6)
C7—N2—C6	122.7 (6)	C9—C8—H8	116.8
C7—N2—Cu1	125.4 (4)	C7—C8—H8	116.8
C6—N2—Cu1	112.0 (4)	O2—C9—C8	124.9 (6)
C2—C1—H1A	109.5	O2—C9—C10	114.5 (7)
C2—C1—H1B	109.5	C8—C9—C10	120.6 (6)
H1A—C1—H1B	109.5	C9—C10—H10A	109.5
C2—C1—H1C	109.5	C9—C10—H10B	109.5
H1A—C1—H1C	109.5	H10A—C10—H10B	109.5
H1B—C1—H1C	109.5	C9—C10—H10C	109.5
O1—C2—C3	125.9 (5)	H10A—C10—H10C	109.5
O1—C2—C1	113.6 (5)	H10B—C10—H10C	109.5
C3—C2—C1	120.5 (5)	C4—C11—H11A	109.5
C2—C3—C4	125.8 (5)	C4—C11—H11B	109.5
C2—C3—H3	117.1	H11A—C11—H11B	109.5
C4—C3—H3	117.1	C4—C11—H11C	109.5
N1—C4—C3	122.8 (5)	H11A—C11—H11C	109.5
N1—C4—C11	120.2 (5)	H11B—C11—H11C	109.5
C3—C4—C11	117.0 (5)	C7—C12—H12A	109.5
C6—C5—N1	113.2 (6)	C7—C12—H12B	109.5
C6—C5—H5A	108.9	H12A—C12—H12B	109.5
N1—C5—H5A	108.9	C7—C12—H12C	109.5
C6—C5—H5B	108.9	H12A—C12—H12C	109.5
N1—C5—H5B	108.9	H12B—C12—H12C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1Wⁱ	0.96	2.58	3.466 (9)	154
C6—H6B···O1Wⁱ	0.97	2.44	3.303 (11)	149
O1W—H1WA···O2	0.79 (2)	2.29 (14)	2.862 (8)	130 (13)

Symmetry code: (i) x−1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₂H₁₈N₂O₂)]·0.25H₂O
M_r	290.33
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	17.0029 (7), 8.0198 (3), 19.6532 (7)
V (Å³)	2679.91 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.24 × 0.21 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.697, 0.817
No. of measured, independent and observed [I > 2σ(I)] reflections	22704, 3338, 1745
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.190, 1.07
No. of reflections	3338
No. of parameters	166
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Cu1—O2	1.897 (4)	Cu1—N2	1.922 (4)
Cu1—O1	1.901 (4)	Cu1—N1	1.926 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1Wⁱ	0.96	2.58	3.466 (9)	154
C6—H6B···O1Wⁱ	0.97	2.44	3.303 (11)	149
O1W—H1WA···O2	0.79 (2)	2.29 (14)	2.862 (8)	130 (13)

Symmetry code: (i) x−1/2, y−1/2, −z+1/2.

Footnotes

‡Department of Chemistry, University of Karachi, Karachi 75270, Pakistan.

Acknowledgements

MA expresses his gratitude to the PCSIR Laboratories Complex, Karachi, the Department of Chemistry, University of Karachi, and the Department of Chemistry, GC University, Lahore, for providing financial support, research facilities and X-ray diffraction facilities, respectively. MNA also acknowledges Professor Helen Stoeckli-Evans, Switzerland, for guidance about the final refinement.

References

Aslam, M., Anis, I., Afza, N., Ali, B. & Shah, M. R. (2012). J. Chem. Soc. Pak. 34, 391–395. CAS Google Scholar
Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page m670

doi:10.1107/S1600536812017102

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[4,4′-(Ethane-1,2-diyldi­nitrilo)­bis­­(pent-2-en-2-olato)]copper(II) 0.25-hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

metal-organic compounds

[4,4′-(Ethane-1,2-diyldinitrilo)bis(pent-2-en-2-olato)]copper(II) 0.25-hydrate