Crystal structure of {2-[({2-[(2-amino-eth-yl)amino]-eth-yl}imino)-meth-yl]pheno-lato}aqua-copper(II) bromide.

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 mol-ecule 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 nitro-gen) and the bromide ion contribute to the formation of the N-H⋯Br, O-H⋯Br and O-H⋯O hydrogen bonds, which link mol-ecules into chains along [01-1].

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 ▶).

Experimental

Crystal data

[Cu(C11H16N3O)(H2O)]Br

M = 367.73

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.097

S = 0.95

4004 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.38 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814017590/rn2126sup1.cif

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

Click here for additional data file.

. DOI: 10.1107/S1600536814017590/rn2126fig1.tif

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.

Click here for additional data file.

. DOI: 10.1107/S1600536814017590/rn2126fig2.tif

Crystal packing of the title compound with hydrogen bonds shown as dashed lines.

CCDC reference: 1017209

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Cu(C11H16N3O)(H2O)]Br	F(000) = 740
Mr = 367.73	Dx = 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

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

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(Fo2) + (0.0308P)2] where P = (Fo2 + 2Fc2)/3
4004 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.98 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) .