Bis(2-{[2-(isopropyl­aza­nium­yl)eth­yl]imino­meth­yl}-6-meth­oxy­phenolato)copper(II) bis­(thio­cyanate)

Yuan, L.

doi:10.1107/S1600536811001322

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m201

doi:10.1107/S1600536811001322

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Bis(2-{[2-(isopropylazaniumyl)ethyl]iminomethyl}-6-methoxyphenolato)copper(II) bis(thiocyanate)

Lin Yuan ^a ^*

^aCollege of Chemistry and Biology Engineering, Yichun University, Yichun 336000, People's Republic of China
^*Correspondence e-mail: yuanlin_ycu@126.com

(Received 6 January 2011; accepted 10 January 2011; online 15 January 2011)

The asymmetric unit of the title compound, [Cu(C₁₃H₂₀N₂O₂)₂](NCS)₂, contains one half-dication, located on an inversion center, and one thiocyanate anion. Each Cu^II atom is four-coordinated by two phenolate O and two imine N atoms from two symmetry-related Schiff base 2-{[2-(isopropylazaniumyl)ethyl]iminomethyl}-6-methoxyphenolate (L) ligands in a distorted square-planar geometry. The ammonium groups are involved in the formation of N—H⋯O and N—H⋯N hydrogen bonds, which link one dication and two anions into an electroneutral cluster. When very weak Cu—N interactions with a distance of 2.910 (5) Å between the metal and the thiocyanate anions in apical positions are considered, the secondary coordination polyhedron is a very elongated CuN₄O₂ octahedron.

Related literature

For background to copper(II) complexes with Schiff base ligands, see: Fernandez et al. (2010 ); Biswas et al. (2010 ); Chakraborty et al. (2010 ). For related complexes, see: Ji & Lu (2010 ); Cai (2009 ); Xia et al. (2008 ); Suleiman Gwaram et al. (2010 ); Ma (2008 ).

Experimental

Crystal data

[Cu(C₁₃H₂₀N₂O₂)₂](NCS)₂
M_r = 652.32
Orthorhombic, P b c a
a = 13.5307 (12) Å
b = 9.7992 (9) Å
c = 24.114 (2) Å
V = 3197.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.848, T_max = 0.882
13234 measured reflections
2406 independent reflections
1666 reflections with I > 2σ(I)
R_int = 0.063
θ_max = 23.8°

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.143
S = 1.15
2406 reflections
190 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3	0.90	2.13	2.972 (10)	155
N2—H2B⋯O1ⁱ	0.90	1.87	2.665 (6)	147
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001322/cv5037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001322/cv5037Isup2.hkl

checkCIF report

Comment top

Copper(II) complexes with Schiff bases have been extensively studied (Fernandez et al., 2010; Biswas et al., 2010; Chakraborty et al., 2010). In this paper, we present the title compound (I) - a new copper(II) complex with the Schiff base ligand 2-[(2-isopropylaminoethylimino)methyl]-6-methoxyphenol.

In (I) (Fig. 1), the Cu center is four-coordinated by two phenolate O and two imine N atoms from two Schiff base ligands in a distorted square-planar geometry. The coordinate bond lengths and angles are comparable with those observed in similar complexes (Ji & Lu, 2010; Cai, 2009; Xia et al., 2008; Suleiman Gwaram et al., 2010; Ma, 2008). Ammonium groups are involved in formation of N—H···O and N—H···N hydrogen bonds (Table 1), which link one dication and two anions into electroneutral cluster, where thiocyanate anions can also be considered as ligands coordinating Cu center in apical positions [Cu1—N3 2.910 (5) Å].

Related literature top

For background to copper(II) complexes with Schiff base ligands, see: Fernandez et al. (2010); Biswas et al. (2010); Chakraborty et al. (2010). For related complexes, see: Ji & Lu (2010); Cai (2009); Xia et al. (2008); Suleiman Gwaram et al. (2010); Ma (2008).

Experimental top

Equimolar quantities (0.1 mmol each) of 3-methoxysalicylaldehyde, N-isopropylethane-1,2-diamine, ammonium thiocyanate, and Cu(CH₃COO)₂.H₂O were mixed and stirred in methanol for 30 min at reflux. After keeping the filtrate in an air for a few days, blue block crystals were formed.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. Unlabelled atoms are related with labelled ones by symmetry operation (- x, 1 - y, 2 - z).

Bis(2-{[2-(isopropylazaniumyl)ethyl]iminomethyl}-6-methoxyphenolato)copper(II) bis(thiocyanate) top

Crystal data top

[Cu(C₁₃H₂₀N₂O₂)₂](NCS)₂	D_x = 1.355 Mg m⁻³
M_r = 652.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1594 reflections
a = 13.5307 (12) Å	θ = 2.3–24.5°
b = 9.7992 (9) Å	µ = 0.86 mm⁻¹
c = 24.114 (2) Å	T = 298 K
V = 3197.3 (5) Å³	Block, blue
Z = 4	0.20 × 0.18 × 0.15 mm
F(000) = 1372

Data collection top

Bruker SMART CCD area-detector diffractometer	2406 independent reflections
Radiation source: fine-focus sealed tube	1666 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 23.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.848, T_max = 0.882	k = −11→8
13234 measured reflections	l = −27→27

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + 13.3941P] where P = (F_o² + 2F_c²)/3
2406 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.38 e Å⁻³
6 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu(C₁₃H₂₀N₂O₂)₂](NCS)₂	V = 3197.3 (5) Å³
M_r = 652.32	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 13.5307 (12) Å	µ = 0.86 mm⁻¹
b = 9.7992 (9) Å	T = 298 K
c = 24.114 (2) Å	0.20 × 0.18 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2406 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1666 reflections with I > 2σ(I)
T_min = 0.848, T_max = 0.882	R_int = 0.063
13234 measured reflections	θ_max = 23.8°

Refinement top

R[F² > 2σ(F²)] = 0.078	6 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + 13.3941P] where P = (F_o² + 2F_c²)/3
2406 reflections	Δρ_max = 0.38 e Å⁻³
190 parameters	Δρ_min = −0.36 e Å⁻³

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	0.0000	0.5000	1.0000	0.0565 (4)
N1	0.1018 (4)	0.3629 (5)	0.97413 (19)	0.0449 (13)
N2	0.0401 (4)	0.4022 (5)	0.85934 (19)	0.0496 (14)
H2A	0.0758	0.4746	0.8706	0.059*
H2B	−0.0187	0.4064	0.8767	0.059*
N3	0.0998 (7)	0.6598 (8)	0.9151 (4)	0.112 (3)
O1	0.0858 (3)	0.5576 (5)	1.05728 (17)	0.0600 (13)
O2	0.1714 (4)	0.7103 (5)	1.12935 (19)	0.0683 (14)
S1	0.1299 (2)	0.8802 (4)	0.84850 (14)	0.1397 (13)
C1	0.2387 (5)	0.4671 (7)	1.0238 (2)	0.0493 (17)
C2	0.1830 (5)	0.5544 (7)	1.0579 (2)	0.0484 (16)
C3	0.2338 (5)	0.6371 (7)	1.0960 (3)	0.0539 (17)
C4	0.3351 (5)	0.6389 (8)	1.0981 (3)	0.063 (2)
H4	0.3672	0.6978	1.1224	0.075*
C5	0.3903 (5)	0.5527 (8)	1.0640 (3)	0.066 (2)
H5	0.4590	0.5537	1.0657	0.079*
C6	0.3431 (5)	0.4669 (7)	1.0282 (3)	0.0589 (19)
H6	0.3800	0.4075	1.0063	0.071*
C7	0.1925 (5)	0.3692 (7)	0.9874 (2)	0.0525 (17)
H7	0.2338	0.3034	0.9720	0.063*
C8	0.0748 (5)	0.2484 (6)	0.9380 (2)	0.0536 (17)
H8A	0.0056	0.2269	0.9436	0.064*
H8B	0.1131	0.1690	0.9487	0.064*
C9	0.0919 (5)	0.2770 (6)	0.8775 (3)	0.0560 (18)
H9A	0.1622	0.2872	0.8708	0.067*
H9B	0.0687	0.2002	0.8557	0.067*
C10	0.0230 (6)	0.4153 (7)	0.7987 (3)	0.064 (2)
H10	−0.0103	0.3324	0.7857	0.077*
C11	0.1193 (7)	0.4276 (10)	0.7687 (3)	0.114 (4)
H11A	0.1546	0.3429	0.7713	0.172*
H11B	0.1579	0.4991	0.7851	0.172*
H11C	0.1072	0.4487	0.7304	0.172*
C12	−0.0447 (7)	0.5355 (8)	0.7880 (3)	0.098 (3)
H12A	−0.1033	0.5264	0.8101	0.147*
H12B	−0.0624	0.5378	0.7495	0.147*
H12C	−0.0112	0.6186	0.7977	0.147*
C13	0.2134 (6)	0.8058 (8)	1.1669 (3)	0.084 (3)
H13A	0.2598	0.7600	1.1906	0.127*
H13B	0.1621	0.8459	1.1890	0.127*
H13C	0.2468	0.8761	1.1464	0.127*
C14	0.1133 (7)	0.7473 (10)	0.8862 (4)	0.097 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0503 (6)	0.0653 (7)	0.0539 (6)	0.0066 (7)	−0.0009 (6)	−0.0144 (7)
N1	0.047 (3)	0.046 (3)	0.041 (3)	−0.004 (3)	0.005 (3)	0.002 (3)
N2	0.058 (3)	0.050 (3)	0.041 (3)	0.013 (3)	0.009 (3)	−0.001 (3)
N3	0.137 (6)	0.072 (5)	0.127 (6)	0.006 (5)	−0.054 (5)	0.004 (5)
O1	0.049 (3)	0.080 (3)	0.051 (3)	0.004 (2)	0.001 (2)	−0.016 (2)
O2	0.069 (3)	0.072 (3)	0.064 (3)	0.003 (3)	−0.011 (3)	−0.018 (3)
S1	0.120 (2)	0.160 (3)	0.139 (3)	0.040 (2)	0.023 (2)	0.056 (2)
C1	0.050 (4)	0.057 (4)	0.041 (3)	0.008 (3)	0.005 (3)	0.007 (3)
C2	0.050 (4)	0.057 (4)	0.039 (4)	−0.001 (3)	−0.004 (3)	0.008 (3)
C3	0.065 (5)	0.051 (4)	0.047 (4)	0.001 (4)	0.001 (4)	0.006 (3)
C4	0.066 (5)	0.063 (5)	0.060 (5)	−0.017 (4)	−0.014 (4)	0.017 (4)
C5	0.050 (5)	0.077 (5)	0.071 (5)	−0.006 (4)	−0.004 (4)	0.015 (4)
C6	0.054 (4)	0.065 (5)	0.058 (4)	0.003 (4)	0.009 (4)	0.013 (4)
C7	0.066 (5)	0.053 (4)	0.039 (4)	0.007 (4)	0.015 (3)	0.004 (3)
C8	0.066 (5)	0.045 (4)	0.050 (4)	0.007 (4)	0.005 (3)	0.001 (3)
C9	0.073 (5)	0.050 (4)	0.046 (4)	0.014 (4)	−0.006 (4)	−0.005 (3)
C10	0.092 (6)	0.061 (5)	0.040 (4)	0.006 (4)	0.001 (4)	−0.001 (4)
C11	0.152 (9)	0.138 (9)	0.053 (5)	0.033 (7)	0.045 (6)	0.019 (5)
C12	0.152 (9)	0.084 (6)	0.058 (5)	0.033 (6)	−0.032 (5)	0.008 (4)
C13	0.109 (7)	0.072 (5)	0.071 (5)	0.003 (5)	−0.020 (5)	−0.019 (4)
C14	0.102 (7)	0.076 (6)	0.114 (8)	0.008 (6)	−0.041 (7)	−0.021 (6)

Geometric parameters (Å, º) top

Cu1—O1ⁱ	1.891 (4)	C5—C6	1.364 (9)
Cu1—O1	1.891 (4)	C5—H5	0.9300
Cu1—N1ⁱ	2.023 (5)	C6—H6	0.9300
Cu1—N1	2.023 (5)	C7—H7	0.9300
N1—C7	1.271 (8)	C8—C9	1.504 (8)
N1—C8	1.466 (7)	C8—H8A	0.9700
N2—C9	1.480 (7)	C8—H8B	0.9700
N2—C10	1.486 (7)	C9—H9A	0.9700
N2—H2A	0.9001	C9—H9B	0.9700
N2—H2B	0.9000	C10—C11	1.496 (10)
N3—C14	1.120 (11)	C10—C12	1.513 (9)
O1—C2	1.316 (7)	C10—H10	0.9800
O2—C3	1.370 (7)	C11—H11A	0.9600
O2—C13	1.421 (8)	C11—H11B	0.9600
S1—C14	1.603 (11)	C11—H11C	0.9600
C1—C2	1.404 (8)	C12—H12A	0.9600
C1—C6	1.417 (9)	C12—H12B	0.9600
C1—C7	1.443 (9)	C12—H12C	0.9600
C2—C3	1.405 (9)	C13—H13A	0.9600
C3—C4	1.372 (9)	C13—H13B	0.9600
C4—C5	1.396 (10)	C13—H13C	0.9600
C4—H4	0.9300

O1ⁱ—Cu1—O1	180	N1—C8—C9	113.3 (5)
O1ⁱ—Cu1—N1ⁱ	90.3 (2)	N1—C8—H8A	108.9
O1—Cu1—N1ⁱ	89.7 (2)	C9—C8—H8A	108.9
O1ⁱ—Cu1—N1	89.7 (2)	N1—C8—H8B	108.9
O1—Cu1—N1	90.3 (2)	C9—C8—H8B	108.9
N1ⁱ—Cu1—N1	180.0 (3)	H8A—C8—H8B	107.7
C7—N1—C8	115.3 (6)	N2—C9—C8	111.6 (5)
C7—N1—Cu1	123.2 (5)	N2—C9—H9A	109.3
C8—N1—Cu1	121.4 (4)	C8—C9—H9A	109.3
C9—N2—C10	115.9 (5)	N2—C9—H9B	109.3
C9—N2—H2A	108.1	C8—C9—H9B	109.3
C10—N2—H2A	108.2	H9A—C9—H9B	108.0
C9—N2—H2B	108.6	N2—C10—C11	110.3 (6)
C10—N2—H2B	108.5	N2—C10—C12	109.2 (6)
H2A—N2—H2B	107.4	C11—C10—C12	112.5 (7)
C2—O1—Cu1	127.9 (4)	N2—C10—H10	108.3
C3—O2—C13	118.2 (6)	C11—C10—H10	108.3
C2—C1—C6	119.6 (6)	C12—C10—H10	108.3
C2—C1—C7	121.9 (6)	C10—C11—H11A	109.5
C6—C1—C7	118.4 (6)	C10—C11—H11B	109.5
O1—C2—C1	123.0 (6)	H11A—C11—H11B	109.5
O1—C2—C3	118.8 (6)	C10—C11—H11C	109.5
C1—C2—C3	118.1 (6)	H11A—C11—H11C	109.5
O2—C3—C4	126.0 (7)	H11B—C11—H11C	109.5
O2—C3—C2	112.7 (6)	C10—C12—H12A	109.5
C4—C3—C2	121.3 (7)	C10—C12—H12B	109.5
C3—C4—C5	120.3 (7)	H12A—C12—H12B	109.5
C3—C4—H4	119.8	C10—C12—H12C	109.5
C5—C4—H4	119.8	H12A—C12—H12C	109.5
C6—C5—C4	119.8 (7)	H12B—C12—H12C	109.5
C6—C5—H5	120.1	O2—C13—H13A	109.5
C4—C5—H5	120.1	O2—C13—H13B	109.5
C5—C6—C1	120.8 (7)	H13A—C13—H13B	109.5
C5—C6—H6	119.6	O2—C13—H13C	109.5
C1—C6—H6	119.6	H13A—C13—H13C	109.5
N1—C7—C1	127.2 (6)	H13B—C13—H13C	109.5
N1—C7—H7	116.4	N3—C14—S1	175.6 (11)
C1—C7—H7	116.4

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.90	2.13	2.972 (10)	155
N2—H2B···O1ⁱ	0.90	1.87	2.665 (6)	147

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₂₀N₂O₂)₂](NCS)₂
M_r	652.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.5307 (12), 9.7992 (9), 24.114 (2)
V (Å³)	3197.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.848, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	13234, 2406, 1666
R_int	0.063
θ_max (°)	23.8
(sin θ/λ)_max (Å⁻¹)	0.568

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.143, 1.15
No. of reflections	2406
No. of parameters	190
No. of restraints	6
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + 13.3941P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.36

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.90	2.13	2.972 (10)	155
N2—H2B···O1ⁱ	0.90	1.87	2.665 (6)	147

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

This work was supported by Yichun University.

References

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m201

doi:10.1107/S1600536811001322

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

Bis(2-{[2-(iso­propyl­aza­nium­yl)eth­yl]imino­meth­yl}-6-meth­­oxy­phenolato)copper(II) bis­­(thio­cyanate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(2-{[2-(isopropylazaniumyl)ethyl]iminomethyl}-6-methoxyphenolato)copper(II) bis(thiocyanate)