{4,4′-Dimeth­oxy-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methanylyl­idene)]diphenolato}copper(II) monohydrate

Ganji, F.; Kargar, H.; Kia, R.; Mirkhani, V.; Tahir, M.N.

doi:10.1107/S1600536812038135

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1255

https://doi.org/10.1107/S1600536812038135

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{4,4′-Dimethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]diphenolato}copper(II) monohydrate

Fatemeh Ganji,^a Hadi Kargar,^a Reza Kia,^b ^* Valiollah Mirkhani ^c and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of IRAN, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, ^cDepartment of Chemistry, University of Isfahan, 81746-73441, Isfahan, Iran, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: zsrkk@yahoo.com, dmntahir_uos@yahoo.com

(Received 20 July 2012; accepted 5 September 2012; online 12 September 2012)

The asymmetric unit of the title compound, [Cu(C₂₁H₂₄N₂O₄)]·H₂O, comprises half of a Schiff base complex and a water molecule. The Cu^II atom, water molecule and one C atom of the central propylene segment are located on a twofold rotation axis. The geometry around the Cu^II atom is distorted square-planar, supported by the N₂O₂ donor atoms of the coordinating ligand. The dihedral angle between the symmetry-related benzene rings is 42.56 (19)°. In the crystal, O—H⋯O hydrogen bonds involving the water molecule make an R₂¹(6) ring motif. Complex molecules are linked into a chain along the c axis via C—H⋯O interactions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For applications of Schiff bases in coordination chemistry, see, for example: Granovski et al. (1993 ); Blower et al. (1998 ). For related structures, see, for example: Ghaemi et al. (2011 ); Kargar et al. (2011 , 2012 ).

Experimental

Crystal data

[Cu(C₂₁H₂₄N₂O₄)]·H₂O
M_r = 449.98
Orthorhombic, P b c n
a = 20.567 (2) Å
b = 12.2647 (14) Å
c = 8.4287 (7) Å
V = 2126.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 291 K
0.21 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.256, T_max = 0.535
17546 measured reflections
2620 independent reflections
1113 reflections with I > 2σ(I)
R_int = 0.115

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.140
S = 0.98
2620 reflections
134 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Cu1	1.930 (3)
Cu1—O1	1.899 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1ⁱ	0.89	2.43	3.024 (5)	124
C9—H9A⋯O1ⁱⁱ	0.97	2.59	3.432 (5)	145
Symmetry codes: (i) $[-x+1, y, -z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812038135/kp2436sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038135/kp2436Isup2.hkl

checkCIF report

Comment top

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the ease of preparation and structural variations (Granovski et al., 1993; Blower et al., (1998). In continuation of our work on the crystal structures of Schiff base metal complexes (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011), we determined the X-ray structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) comprises a a half of Schiff base complex. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structure (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011). The geometry around Cu^II is a distorted square-planar which is supported by the N₂O₂ donor atoms of the coordinated Schiff base ligand (Table 1). The dihedral angle between the substituted benzene rings is 42.56 (19)°. Interamolecular O—H···O hydrogen bonds make R¹₂(6) ring motif (Bernstein et al., 1995). The dihedral angle between the symmetry-related benzene rings is 45.54 (19)°. In the crystal structure the molecules are linked together along the c axis, forming a chain through the intermolecular C—H···O interactions (Table 2, Fig. 2).

Related literature top

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For applications of Schiff bases in coordination chemistry, see, for example: Granovski et al. (1993); Blower et al. (1998). For related structures, see, for example: Ghaemi, et al., (2011); Kargar et al. (2011, 2012).

Experimental top

The title compound was synthesized by adding 5-methoxy-salicylaldehyde-2,2-dimethyl-1, 3-propanediamine (2 mmol) to a solution of CuCl₂. 4H₂O (2.1 mmol) in ethanol (30 mL). The mixture was refluxed with stirring for 30 min. The resultant solution was filtered. Dark-green single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Structure description top

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For applications of Schiff bases in coordination chemistry, see, for example: Granovski et al. (1993); Blower et al. (1998). For related structures, see, for example: Ghaemi, et al., (2011); Kargar et al. (2011, 2012).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering.Intermolecular hydrogen bonds between the complex and crystal water molecule are shown (dashed lines).
	Fig. 2. A part of the packing diagram of the title compound showing a chain formed through the intermolecular C—H···O intearctions along the c axis (dashed lines). Only the H atoms involved in the interactions are shown.

{4,4'-Dimethoxy-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethanylylidene)]diphenolato}copper(II) monohydrate top

Crystal data top

[Cu(C₂₁H₂₄N₂O₄)]·H₂O	F(000) = 940
M_r = 449.98	D_x = 1.406 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2169 reflections
a = 20.567 (2) Å	θ = 2.5–27.4°
b = 12.2647 (14) Å	µ = 1.06 mm⁻¹
c = 8.4287 (7) Å	T = 291 K
V = 2126.1 (4) Å³	Block, dark-green
Z = 4	0.21 × 0.14 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2620 independent reflections
Radiation source: fine-focus sealed tube	1113 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.115
φ and ω scans	θ_max = 28.3°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→27
T_min = 0.256, T_max = 0.535	k = −16→16
17546 measured reflections	l = −10→8

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0498P)² + 0.1009P] where P = (F_o² + 2F_c²)/3
2620 reflections	(Δ/σ)_max < 0.001
134 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu(C₂₁H₂₄N₂O₄)]·H₂O	V = 2126.1 (4) Å³
M_r = 449.98	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 20.567 (2) Å	µ = 1.06 mm⁻¹
b = 12.2647 (14) Å	T = 291 K
c = 8.4287 (7) Å	0.21 × 0.14 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2620 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1113 reflections with I > 2σ(I)
T_min = 0.256, T_max = 0.535	R_int = 0.115
17546 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.98	Δρ_max = 0.28 e Å⁻³
2620 reflections	Δρ_min = −0.36 e Å⁻³
134 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1W	0.5000	0.1449 (4)	−0.2500	0.136 (2)
H1W	0.5199	0.1907	−0.1831	0.205*
N1	0.44802 (15)	0.5832 (3)	−0.1447 (3)	0.0486 (8)
C1	0.37450 (19)	0.3777 (3)	−0.1853 (4)	0.0476 (10)
C2	0.3307 (2)	0.2908 (3)	−0.2041 (5)	0.0616 (12)
H1	0.3448	0.2271	−0.2531	0.074*
C3	0.2675 (2)	0.2974 (3)	−0.1520 (5)	0.0642 (12)
H3	0.2395	0.2389	−0.1682	0.077*
C4	0.24498 (19)	0.3899 (3)	−0.0757 (5)	0.0547 (11)
C5	0.28556 (19)	0.4760 (3)	−0.0581 (5)	0.0516 (10)
H5	0.2703	0.5388	−0.0087	0.062*
C6	0.35058 (18)	0.4730 (3)	−0.1130 (4)	0.0459 (9)
C7	0.1550 (2)	0.4783 (4)	0.0455 (6)	0.0796 (15)
H7A	0.1793	0.4947	0.1399	0.119*
H7B	0.1104	0.4650	0.0730	0.119*
H7C	0.1575	0.5389	−0.0264	0.119*
C8	0.38928 (18)	0.5688 (3)	−0.0937 (4)	0.0480 (10)
H8	0.3704	0.6265	−0.0390	0.058*
C9	0.4810 (2)	0.6853 (4)	−0.1061 (5)	0.0596 (12)
H9A	0.5197	0.6691	−0.0450	0.072*
H9B	0.4525	0.7290	−0.0400	0.072*
C10	0.5000	0.7548 (5)	−0.2500	0.0626 (16)
C11	0.4427 (3)	0.8223 (5)	−0.3009 (7)	0.139 (3)
H11A	0.4546	0.8661	−0.3906	0.209*
H11B	0.4295	0.8688	−0.2150	0.209*
H11C	0.4073	0.7751	−0.3294	0.209*
Cu1	0.5000	0.47397 (6)	−0.2500	0.0496 (3)
O1	0.43439 (12)	0.3654 (2)	−0.2370 (3)	0.0530 (7)
O3	0.18104 (14)	0.3856 (3)	−0.0270 (4)	0.0734 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.216 (7)	0.081 (4)	0.113 (5)	0.000	−0.022 (4)	0.000
N1	0.045 (2)	0.060 (2)	0.041 (2)	−0.0107 (18)	0.0028 (15)	−0.0045 (16)
C1	0.048 (3)	0.052 (3)	0.043 (2)	−0.001 (2)	0.0030 (19)	0.0007 (19)
C2	0.058 (3)	0.049 (3)	0.078 (3)	−0.002 (2)	0.010 (2)	−0.009 (2)
C3	0.054 (3)	0.054 (3)	0.085 (3)	−0.011 (2)	0.010 (2)	−0.005 (2)
C4	0.040 (2)	0.059 (3)	0.065 (3)	−0.001 (2)	0.003 (2)	0.004 (2)
C5	0.046 (2)	0.054 (3)	0.054 (2)	0.003 (2)	0.005 (2)	−0.003 (2)
C6	0.043 (2)	0.048 (2)	0.046 (2)	0.000 (2)	−0.0001 (18)	0.000 (2)
C7	0.053 (3)	0.091 (4)	0.095 (4)	−0.008 (3)	0.019 (3)	−0.006 (3)
C8	0.048 (2)	0.050 (3)	0.046 (2)	0.002 (2)	0.002 (2)	−0.0086 (19)
C9	0.056 (3)	0.068 (3)	0.054 (3)	−0.015 (2)	0.003 (2)	−0.008 (2)
C10	0.072 (4)	0.054 (4)	0.062 (4)	0.000	0.006 (4)	0.000
C11	0.178 (7)	0.137 (5)	0.102 (4)	0.106 (5)	0.047 (4)	0.041 (4)
Cu1	0.0406 (4)	0.0587 (5)	0.0494 (4)	0.000	0.0029 (3)	0.000
O1	0.0433 (15)	0.0533 (17)	0.0624 (18)	0.0010 (12)	0.0043 (15)	−0.0051 (14)
O3	0.0435 (17)	0.073 (2)	0.104 (3)	−0.0068 (16)	0.0141 (16)	−0.0039 (18)

Geometric parameters (Å, º) top

O1W—H1W	0.8940	C7—H7A	0.9600
N1—C8	1.295 (4)	C7—H7B	0.9600
N1—C9	1.460 (5)	C7—H7C	0.9600
N1—Cu1	1.930 (3)	C8—H8	0.9300
C1—O1	1.315 (4)	C9—C10	1.533 (5)
C1—C2	1.405 (5)	C9—H9A	0.9691
C1—C6	1.407 (5)	C9—H9B	0.9699
C2—C3	1.374 (5)	C10—C11ⁱ	1.503 (6)
C2—H1	0.9300	C10—C11	1.503 (6)
C3—C4	1.384 (5)	C10—C9ⁱ	1.533 (5)
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.354 (5)	C11—H11B	0.9600
C4—O3	1.379 (4)	C11—H11C	0.9600
C5—C6	1.415 (5)	Cu1—O1	1.899 (3)
C5—H5	0.9300	Cu1—O1ⁱ	1.899 (3)
C6—C8	1.429 (5)	Cu1—N1ⁱ	1.930 (3)
C7—O3	1.398 (5)

C8—N1—C9	118.5 (3)	N1—C8—H8	116.8
C8—N1—Cu1	125.1 (3)	C6—C8—H8	116.8
C9—N1—Cu1	116.1 (3)	N1—C9—C10	114.7 (3)
O1—C1—C2	118.5 (4)	N1—C9—H9A	108.9
O1—C1—C6	124.5 (4)	C10—C9—H9A	108.9
C2—C1—C6	117.0 (4)	N1—C9—H9B	108.8
C3—C2—C1	121.8 (4)	C10—C9—H9B	107.6
C3—C2—H1	119.1	H9A—C9—H9B	107.7
C1—C2—H1	119.1	C11ⁱ—C10—C11	113.1 (7)
C2—C3—C4	120.8 (4)	C11ⁱ—C10—C9ⁱ	109.4 (3)
C2—C3—H3	119.6	C11—C10—C9ⁱ	106.3 (3)
C4—C3—H3	119.6	C11ⁱ—C10—C9	106.3 (3)
C5—C4—O3	125.9 (4)	C11—C10—C9	109.4 (3)
C5—C4—C3	119.0 (4)	C9ⁱ—C10—C9	112.5 (5)
O3—C4—C3	115.2 (4)	C10—C11—H11A	109.5
C4—C5—C6	121.7 (4)	C10—C11—H11B	109.5
C4—C5—H5	119.1	H11A—C11—H11B	109.5
C6—C5—H5	119.1	C10—C11—H11C	109.5
C1—C6—C5	119.6 (4)	H11A—C11—H11C	109.5
C1—C6—C8	122.5 (4)	H11B—C11—H11C	109.5
C5—C6—C8	117.9 (4)	O1—Cu1—O1ⁱ	90.97 (15)
O3—C7—H7A	109.5	O1—Cu1—N1ⁱ	155.08 (11)
O3—C7—H7B	109.5	O1ⁱ—Cu1—N1ⁱ	93.83 (12)
H7A—C7—H7B	109.5	O1—Cu1—N1	93.83 (12)
O3—C7—H7C	109.5	O1ⁱ—Cu1—N1	155.08 (11)
H7A—C7—H7C	109.5	N1ⁱ—Cu1—N1	92.05 (18)
H7B—C7—H7C	109.5	C1—O1—Cu1	127.2 (2)
N1—C8—C6	126.5 (4)	C4—O3—C7	117.6 (3)

O1—C1—C2—C3	179.5 (4)	Cu1—N1—C9—C10	68.1 (4)
C6—C1—C2—C3	−1.1 (6)	N1—C9—C10—C11ⁱ	−153.9 (4)
C1—C2—C3—C4	−1.3 (7)	N1—C9—C10—C11	83.7 (5)
C2—C3—C4—C5	2.4 (7)	N1—C9—C10—C9ⁱ	−34.2 (2)
C2—C3—C4—O3	−179.0 (4)	C8—N1—Cu1—O1	−0.3 (3)
O3—C4—C5—C6	−179.6 (4)	C9—N1—Cu1—O1	172.8 (3)
C3—C4—C5—C6	−1.2 (6)	C8—N1—Cu1—O1ⁱ	−100.9 (4)
O1—C1—C6—C5	−178.4 (3)	C9—N1—Cu1—O1ⁱ	72.2 (4)
C2—C1—C6—C5	2.2 (6)	C8—N1—Cu1—N1ⁱ	155.4 (4)
O1—C1—C6—C8	2.4 (6)	C9—N1—Cu1—N1ⁱ	−31.4 (2)
C2—C1—C6—C8	−177.0 (3)	C2—C1—O1—Cu1	171.9 (3)
C4—C5—C6—C1	−1.1 (6)	C6—C1—O1—Cu1	−7.5 (5)
C4—C5—C6—C8	178.1 (3)	O1ⁱ—Cu1—O1—C1	161.4 (3)
C9—N1—C8—C6	−176.9 (3)	N1ⁱ—Cu1—O1—C1	−97.4 (4)
Cu1—N1—C8—C6	−3.9 (5)	N1—Cu1—O1—C1	5.9 (3)
C1—C6—C8—N1	3.7 (6)	C5—C4—O3—C7	0.8 (6)
C5—C6—C8—N1	−175.6 (4)	C3—C4—O3—C7	−177.7 (4)
C8—N1—C9—C10	−118.3 (4)

Symmetry code: (i) −x+1, y, −z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1ⁱ	0.89	2.43	3.024 (5)	124
C9—H9A···O1ⁱⁱ	0.97	2.59	3.432 (5)	145

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

Experimental details

Crystal data
Chemical formula	[Cu(C₂₁H₂₄N₂O₄)]·H₂O
M_r	449.98
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	291
a, b, c (Å)	20.567 (2), 12.2647 (14), 8.4287 (7)
V (Å³)	2126.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.06
Crystal size (mm)	0.21 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.256, 0.535
No. of measured, independent and observed [I > 2σ(I)] reflections	17546, 2620, 1113
R_int	0.115
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.140, 0.98
No. of reflections	2620
No. of parameters	134
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

N1—Cu1

1.930 (3)

Cu1—O1

1.899 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1ⁱ	0.89	2.43	3.024 (5)	124
C9—H9A···O1ⁱⁱ	0.97	2.59	3.432 (5)	145

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

Acknowledgements

HK and FG thank PNU for the financial support. MNT thanks the University of Sargodha for the research facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
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Volume 68| Part 10| October 2012| Page m1255

https://doi.org/10.1107/S1600536812038135

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

{4,4′-Dimeth­­oxy-2,2′-[2,2-di­methyl­propane-1,3-diylbis(nitrilo­methanylyl­­idene)]diphenolato}copper(II) monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{4,4′-Dimethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]diphenolato}copper(II) monohydrate