Crystal structure of {2-[({2-[(2-amino­eth­yl)amino]­eth­yl}imino)­meth­yl]pheno­lato}aqua­copper(II) bromide

Plyuta, N.I.; Rusanova, J.A.; Petrusenko, S.R.; Omelchenko, I.V.

doi:10.1107/S1600536814017590

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages m330-m331

doi:10.1107/S1600536814017590

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Crystal structure of {2-[({2-[(2-aminoethyl)amino]ethyl}imino)methyl]phenolato}aquacopper(II) bromide

Nataliya I. Plyuta,^a Julia A. Rusanova,^a Svitlana R. Petrusenko ^a ^* and Irina V. Omelchenko ^b

^aTaras Shevchenko National University of Kyiv, Department of Inorganic Chemistry, Volodymyrska str. 64/13, 01601 Kyiv, Ukraine, and ^bInstitute for Scintillation Materials, "Institute for Single Crystals", National Academy of Sciences of Ukraine, Lenina ave. 60, Kharkov 61001, Ukraine
^*Correspondence e-mail: spetrusenko@yahoo.com

Edited by G. M. Rosair, Heriot-Watt University, Scotland (Received 14 May 2014; accepted 31 July 2014; online 16 August 2014)

In the mononuclear copper(II) title complex, [Cu(C₁₁H₁₆N₃O)(H₂O)]Br, the Cu^II atom is coordinated by one O and three N atoms of the Schiff base ligand that forms together with one water molecule a slightly distorted [CuN₃O₂] square-pyramidal polyhedron. The deviation of the Cu^II atom from the mean equatorial plane is 0.182 (2) Å. The equatorial plane is nearly coplanar to the aromatic ring of the ligand [angle between planes = 10.4 (1)°], and the water molecule is situated in the apical site. All coordinating atoms (except the imine nitrogen) and the bromide ion contribute to the formation of the N—H⋯Br, O—H⋯Br and O—H⋯O hydrogen bonds, which link molecules into chains along [01-1].

Keywords: crystal structure; copper(II) complex; Schiff base ligand; bromide; hydrogen bonding.

CCDC reference: 1017209

1. Related literature

For structures isotypic with that of the title compound, see: Zhu et al. (2002 , 2004 ); He (2003 ). For the direct synthesis of copper-containing coordination compounds using the salt route, see: Kovbasyuk et al. (1997 ); Pryma et al. (2003 ); Buvaylo et al. (2005 ); Nikitina et al. (2008 ); Vassilyeva et al. (1997 ); Makhankova et al. (2002 ). For the direct synthesis of polynuclear copper-containing complexes, see: Nesterova (Pryma) et al. (2004 ); Nesterova et al. (2005 ).

2. Experimental

2.1. Crystal data

[Cu(C₁₁H₁₆N₃O)(H₂O)]Br
M_r = 367.73
Monoclinic, P 2₁ /c
a = 9.2226 (11) Å
b = 14.0333 (13) Å
c = 10.9206 (11) Å
β = 102.355 (11)°
V = 1380.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.47 mm⁻¹
T = 293 K
0.40 × 0.40 × 0.40 mm

2.2. Data collection

Agilent Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.268, T_max = 0.268
7804 measured reflections
4004 independent reflections
2334 reflections with I > 2σ(I)
R_int = 0.045

2.3. Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.097
S = 0.95
4004 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2OB⋯Br1	0.82	2.51	3.323 (3)	173
N2—H2N⋯Br1	0.85	2.58	3.429 (3)	177
O2—H2OA⋯O1ⁱ	0.82	1.90	2.712 (4)	171
N3—H3NA⋯Br1ⁱⁱ	0.85	2.68	3.499 (3)	164
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009 ); molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1017209

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814017590/rn2126sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814017590/rn2126Isup2.hkl

checkCIF report

Comment top

It has been shown that the direct synthesis is an efficient method to obtain novel homo and heterometallic mono/polynuclear coordination compounds (Kovbasyuk et al., 1997; Vassilyeva et al., 1997; Makhankova et al., 2002; Pryma et al., 2003; Nesterova (Pryma) et al., 2004; Nesterova et al., 2005; Buvaylo et al., 2005; Nikitina et al., 2008). The title compound, [Cu(C₁₁H₁₈N₃O₂)(H₂O)]Br, was obtained unintentionally as the product of an attempted synthesis of a Cu/ Mn heterometallic complex using zerovalent copper and manganese powders, ammonium bromide, salicylic aldehyde and diethylenetriamine in dimethylformamide on air.

As shown in Fig. 1, the Cu^II atom has a slightly distorted square-pyramidal geometry formed by one oxygen and three nitrogen atoms of the Schiff base ligand as well one oxygen atom of the coordinated water molecule. The deviation of the copper atom from the mean equatorial plane is 0.182 (2) Å. The range of Cu–N and Cu–O bond distances in the equatorial plane is 1.918 (3) - 2.018 (3) Å, while the Cu–O axial distance is 2.333 (2) Å. These data are in a good agreement with literature values (Zhu et al.,2002, 2004; He et al., 2003). The equatorial plane is nearly coplanar to the aromatic ring of the ligand [angle between planes is 10.4 (1)°].

In the crystal, OH···O hydrogen bonds form molecular dimers. OH···Br and NH···Br hydrogen bonds link the dimers into chains along the [011] crystallographic direction (See Table containing Hydrogen-bond geometry and Fig.2).

Related literature top

For a monoclinic isomorph of the title compound, see: Zhu et al. (2002, 2004); He (2003). For the direct synthesis of copper-containing coordination compounds using the salt route, see: Kovbasyuk et al. (1997); Pryma et al. (2003); Buvaylo et al. (2005); Nikitina et al. (2008); Vassilyeva et al. (1997); Makhankova et al. (2002). For the direct synthesis of polynuclear copper-containing complexes, see: Nesterova (Pryma) et al. (2004); Nesterova et al. (2005).

Experimental top

The title compound was synthesized by addition of manganese powder 0.055 g (1 mmol), copper powder 0.06 g (1 mmol) and NH₄Br 0.392 g (4 mmol) to the previously prepared Schiff base ligand solution [mixture of salicylic aldehyde 0.21 ml (2 mmol) and diethylenetriamine 0.108 ml (1 mmol) in dimethylformamide (10 ml) which was stirred about 15 min at 323–333 K until the mixture turned yellow]. The total reaction mixture was stirred magnetically for 4 h until the complete dissolution of manganese and copper powders was observed. Dark green crystals that precipitated after 1 day were collected by filtration and dried in air.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Structure of the title compound, with displacement ellipsoids drawn at the 50% probability level for non-H atoms with hydrogen bonds shown as dashed lines.
	Fig. 2. Crystal packing of the title compound with hydrogen bonds shown as dashed lines.

{2-[({2-[(2-Aminoethyl)amino]ethyl}imino)methyl]phenolato}aquacopper(II) bromide top

Crystal data top

[Cu(C₁₁H₁₆N₃O)(H₂O)]Br	F(000) = 740
M_r = 367.73	D_x = 1.769 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1502 reflections
a = 9.2226 (11) Å	θ = 2.9–32.2°
b = 14.0333 (13) Å	µ = 4.47 mm⁻¹
c = 10.9206 (11) Å	T = 293 K
β = 102.355 (11)°	Block, green
V = 1380.7 (3) Å³	0.40 × 0.40 × 0.40 mm
Z = 4

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	4004 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 16.1827 pixels mm^-1	θ_max = 30.0°, θ_min = 2.9°
ω scans	h = −7→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→19
T_min = 0.268, T_max = 0.268	l = −15→12
7804 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0308P)²] where P = (F_o² + 2F_c²)/3
4004 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Cu(C₁₁H₁₆N₃O)(H₂O)]Br	V = 1380.7 (3) Å³
M_r = 367.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2226 (11) Å	µ = 4.47 mm⁻¹
b = 14.0333 (13) Å	T = 293 K
c = 10.9206 (11) Å	0.40 × 0.40 × 0.40 mm
β = 102.355 (11)°

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	4004 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2334 reflections with I > 2σ(I)
T_min = 0.268, T_max = 0.268	R_int = 0.045
7804 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.95	Δρ_max = 0.98 e Å⁻³
4004 reflections	Δρ_min = −0.38 e Å⁻³
163 parameters

Special details top

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.67287 (6)	0.58118 (3)	0.65849 (4)	0.03317 (14)
Br1	0.70894 (6)	0.32849 (3)	0.91251 (4)	0.04828 (15)
O1	0.6489 (3)	0.61004 (19)	0.4836 (2)	0.0412 (7)
O2	0.6414 (3)	0.41770 (17)	0.6240 (2)	0.0401 (7)
H2OA	0.5548	0.4032	0.5949	0.060*
H2OB	0.6614	0.3912	0.6920	0.060*
N1	0.8883 (4)	0.5872 (2)	0.6891 (3)	0.0346 (8)
N2	0.7031 (4)	0.5675 (2)	0.8462 (3)	0.0387 (8)
H2N	0.7059	0.5079	0.8604	0.046*
N3	0.4595 (4)	0.6068 (2)	0.6646 (3)	0.0399 (8)
H3NA	0.4358	0.6632	0.6411	0.048*
H3NB	0.4087	0.5679	0.6132	0.048*
C1	0.9071 (4)	0.6273 (2)	0.4771 (3)	0.0302 (8)
C2	0.7532 (5)	0.6287 (2)	0.4219 (3)	0.0313 (9)
C3	0.7118 (5)	0.6529 (2)	0.2942 (3)	0.0349 (9)
H3	0.6117	0.6542	0.2556	0.042*
C4	0.8153 (5)	0.6747 (3)	0.2252 (4)	0.0424 (11)
H4	0.7837	0.6912	0.1412	0.051*
C5	0.9668 (5)	0.6727 (3)	0.2784 (4)	0.0463 (11)
H5	1.0368	0.6864	0.2309	0.056*
C6	1.0092 (5)	0.6498 (3)	0.4026 (4)	0.0419 (10)
H6	1.1100	0.6491	0.4394	0.050*
C7	0.9648 (5)	0.6070 (2)	0.6085 (4)	0.0366 (9)
H7	1.0673	0.6085	0.6364	0.044*
C8	0.9587 (5)	0.5675 (3)	0.8202 (4)	0.0467 (11)
H8A	1.0528	0.6007	0.8429	0.056*
H8B	0.9771	0.4997	0.8320	0.056*
C9	0.8548 (5)	0.6011 (3)	0.9012 (4)	0.0411 (10)
H9A	0.8868	0.5762	0.9855	0.049*
H9B	0.8561	0.6702	0.9058	0.049*
C10	0.5790 (5)	0.6137 (3)	0.8863 (4)	0.0440 (11)
H10A	0.5935	0.6822	0.8899	0.053*
H10B	0.5728	0.5915	0.9691	0.053*
C11	0.4385 (5)	0.5896 (3)	0.7935 (4)	0.0492 (11)
H11A	0.4132	0.5233	0.8027	0.059*
H11B	0.3576	0.6287	0.8092	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0316 (3)	0.0396 (3)	0.0258 (2)	0.0004 (2)	0.00050 (19)	0.0017 (2)
Br1	0.0532 (3)	0.0425 (2)	0.0456 (3)	−0.0024 (2)	0.0028 (2)	0.0084 (2)
O1	0.0259 (16)	0.0651 (18)	0.0285 (14)	−0.0052 (14)	−0.0029 (12)	0.0099 (13)
O2	0.0341 (17)	0.0430 (15)	0.0378 (15)	−0.0046 (13)	−0.0039 (12)	−0.0007 (13)
N1	0.032 (2)	0.0361 (17)	0.0306 (17)	0.0052 (15)	−0.0046 (14)	−0.0041 (15)
N2	0.053 (2)	0.0278 (16)	0.0327 (18)	−0.0054 (16)	0.0025 (16)	0.0013 (14)
N3	0.037 (2)	0.0425 (18)	0.0396 (19)	−0.0004 (16)	0.0076 (16)	−0.0011 (15)
C1	0.027 (2)	0.0261 (17)	0.036 (2)	0.0005 (17)	0.0039 (17)	−0.0055 (16)
C2	0.033 (2)	0.0300 (19)	0.031 (2)	−0.0043 (18)	0.0052 (17)	−0.0009 (16)
C3	0.035 (2)	0.037 (2)	0.029 (2)	−0.0076 (18)	0.0001 (17)	−0.0034 (16)
C4	0.058 (3)	0.036 (2)	0.035 (2)	−0.004 (2)	0.014 (2)	−0.0020 (18)
C5	0.047 (3)	0.047 (2)	0.052 (3)	0.002 (2)	0.026 (2)	−0.012 (2)
C6	0.032 (3)	0.040 (2)	0.055 (3)	−0.0030 (19)	0.012 (2)	−0.010 (2)
C7	0.024 (2)	0.036 (2)	0.046 (2)	0.0033 (17)	−0.0014 (19)	−0.0055 (18)
C8	0.047 (3)	0.052 (3)	0.032 (2)	0.014 (2)	−0.0111 (19)	0.0004 (19)
C9	0.047 (3)	0.043 (2)	0.028 (2)	0.003 (2)	−0.0043 (19)	0.0004 (18)
C10	0.054 (3)	0.045 (2)	0.036 (2)	−0.002 (2)	0.015 (2)	−0.0047 (18)
C11	0.048 (3)	0.059 (3)	0.043 (3)	−0.008 (2)	0.016 (2)	−0.005 (2)

Geometric parameters (Å, º) top

Cu1—O1	1.919 (3)	C2—C3	1.407 (5)
Cu1—N1	1.945 (3)	C3—C4	1.371 (5)
Cu1—N3	2.016 (3)	C3—H3	0.9300
Cu1—N2	2.018 (3)	C4—C5	1.395 (6)
Cu1—O2	2.333 (2)	C4—H4	0.9300
O1—C2	1.313 (4)	C5—C6	1.367 (6)
O2—H2OA	0.8197	C5—H5	0.9300
O2—H2OB	0.8159	C6—H6	0.9300
N1—C7	1.271 (5)	C7—H7	0.9300
N1—C8	1.466 (5)	C8—C9	1.512 (6)
N2—C10	1.461 (5)	C8—H8A	0.9700
N2—C9	1.477 (5)	C8—H8B	0.9700
N2—H2N	0.8495	C9—H9A	0.9700
N3—C11	1.481 (5)	C9—H9B	0.9700
N3—H3NA	0.8455	C10—C11	1.503 (6)
N3—H3NB	0.8494	C10—H10A	0.9700
C1—C6	1.407 (5)	C10—H10B	0.9700
C1—C2	1.418 (5)	C11—H11A	0.9700
C1—C7	1.447 (5)	C11—H11B	0.9700

O1—Cu1—N1	93.31 (12)	C2—C3—H3	119.1
O1—Cu1—N3	95.17 (12)	C3—C4—C5	121.3 (4)
N1—Cu1—N3	162.80 (13)	C3—C4—H4	119.3
O1—Cu1—N2	173.18 (12)	C5—C4—H4	119.3
N1—Cu1—N2	85.17 (14)	C6—C5—C4	117.8 (4)
N3—Cu1—N2	84.65 (14)	C6—C5—H5	121.1
O1—Cu1—O2	93.61 (10)	C4—C5—H5	121.1
N1—Cu1—O2	99.09 (11)	C5—C6—C1	122.8 (4)
N3—Cu1—O2	95.29 (11)	C5—C6—H6	118.6
N2—Cu1—O2	93.20 (10)	C1—C6—H6	118.6
C2—O1—Cu1	127.7 (2)	N1—C7—C1	126.1 (4)
Cu1—O2—H2OA	112.6	N1—C7—H7	117.0
Cu1—O2—H2OB	107.8	C1—C7—H7	117.0
H2OA—O2—H2OB	104.6	N1—C8—C9	108.0 (3)
C7—N1—C8	121.5 (4)	N1—C8—H8A	110.1
C7—N1—Cu1	126.0 (3)	C9—C8—H8A	110.1
C8—N1—Cu1	112.5 (3)	N1—C8—H8B	110.1
C10—N2—C9	118.1 (3)	C9—C8—H8B	110.1
C10—N2—Cu1	108.4 (2)	H8A—C8—H8B	108.4
C9—N2—Cu1	107.2 (2)	N2—C9—C8	109.0 (3)
C10—N2—H2N	112.2	N2—C9—H9A	109.9
C9—N2—H2N	104.5	C8—C9—H9A	109.9
Cu1—N2—H2N	105.7	N2—C9—H9B	109.9
C11—N3—Cu1	109.3 (3)	C8—C9—H9B	109.9
C11—N3—H3NA	111.3	H9A—C9—H9B	108.3
Cu1—N3—H3NA	110.3	N2—C10—C11	108.4 (3)
C11—N3—H3NB	111.0	N2—C10—H10A	110.0
Cu1—N3—H3NB	105.5	C11—C10—H10A	110.0
H3NA—N3—H3NB	109.3	N2—C10—H10B	110.0
C6—C1—C2	119.0 (4)	C11—C10—H10B	110.0
C6—C1—C7	117.9 (4)	H10A—C10—H10B	108.4
C2—C1—C7	123.1 (4)	N3—C11—C10	109.5 (4)
O1—C2—C3	118.9 (4)	N3—C11—H11A	109.8
O1—C2—C1	123.7 (3)	C10—C11—H11A	109.8
C3—C2—C1	117.3 (4)	N3—C11—H11B	109.8
C4—C3—C2	121.7 (4)	C10—C11—H11B	109.8
C4—C3—H3	119.1	H11A—C11—H11B	108.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2OB···Br1	0.82	2.51	3.323 (3)	173
N2—H2N···Br1	0.85	2.58	3.429 (3)	177
O2—H2OA···O1ⁱ	0.82	1.90	2.712 (4)	171
N3—H3NA···Br1ⁱⁱ	0.85	2.68	3.499 (3)	164

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2OB···Br1	0.82	2.51	3.323 (3)	172.5
N2—H2N···Br1	0.85	2.58	3.429 (3)	177.3
O2—H2OA···O1ⁱ	0.82	1.90	2.712 (4)	170.7
N3—H3NA···Br1ⁱⁱ	0.85	2.68	3.499 (3)	163.9

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

Acknowledgements

This work was partly supported by the State Fund for Fundamental Researches of Ukraine (project 54.3/005).

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Volume 70| Part 9| September 2014| Pages m330-m331

doi:10.1107/S1600536814017590

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

Crystal structure of {2-[({2-[(2-amino­eth­yl)amino]­eth­yl}imino)­meth­yl]pheno­lato}aqua­copper(II) bromide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Crystal structure of {2-[({2-[(2-aminoethyl)amino]ethyl}imino)methyl]phenolato}aquacopper(II) bromide