Bis(μ-2-{1-[2-(dimethyl­amino)­ethyl­imino]­eth­yl}phenolato)bis­[bromido­copper(II)] monohydrate

Suleiman Gwaram, N.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536811022045

metal-organic compounds

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Volume 67| Part 7| July 2011| Page m931

doi:10.1107/S1600536811022045

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Bis(μ-2-{1-[2-(dimethylamino)ethylimino]ethyl}phenolato)bis[bromidocopper(II)] monohydrate

Nura Suleiman Gwaram,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 14 April 2011; accepted 7 June 2011; online 18 June 2011)

In the centrosymmetric dinuclear copper(II) title complex, [Cu₂Br₂(C₁₂H₁₇N₂O)₂]·H₂O, each Cu^II ion is five coordinated in a square-pyramidal geometry by the N,N′,O-tridentate Schiff base, one Br atom and the bridging O atom of the centrosymmetrically related Schiff base. In the crystal, the water molecules link the complex molecules into infinite chains along the b axis via O—H⋯Br and C—H⋯O hydrogen bonds.

Related literature

For the structures of some similar doubly bridged copper(II) complexes, see: Li et al. (2000 ); Rigamonti et al. (2008 ); Suo (2008 ). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984 ).

Experimental

Crystal data

[Cu₂Br₂(C₁₂H₁₇N₂O)₂]·H₂O
M_r = 715.47
Monoclinic, C 2/c
a = 20.754 (4) Å
b = 8.2492 (16) Å
c = 18.521 (4) Å
β = 119.528 (2)°
V = 2759.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 4.47 mm⁻¹
T = 100 K
0.19 × 0.14 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.484, T_max = 0.689
10414 measured reflections
3007 independent reflections
2623 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.060
S = 1.05
3007 reflections
165 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2ⁱ	0.98	2.40	3.299 (3)	152
O2—H2O⋯Br1	0.83 (2)	2.62 (2)	3.4269 (14)	167 (3)
Symmetry code: (i) x, y-1, z.

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: X-SEED (Barbour, 2001 ; Atwood & Barbour, 2003 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811022045/ez2243sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022045/ez2243Isup2.hkl

checkCIF report

Comment top

The title dimeric copper(II) complex was synthesized through the reaction of the in situ prepared Schiff base, N,N-dimethyl-N'-[methyl(2-phenolyl)methylene]ethane-1,2-diamine, with copper(I) bromide. Under the reaction conditions, the Cu^I ion was oxidized to Cu^II and chelated by the deprotonated N,N',O-tridentate Schiff base. Pairs of metal centers are doubly bridged via the phenoxide O atoms around centers of inversion. Within the formed dimer, the Cu···.Cu distance [2.9935 (8) Å] is comparable to those reported for similar structures (Li et al., 2000; Rigamonti et al., 2008; Suo, 2008). The square-pyramidal geometry (τ = 0.11, Addison et al., 1984) around each Cu^II ion is completed by one apically positioned Br atom. The dimeric complex is cocrystallized with one molecule of water whose oxygen atom is situated on a 2-fold rotational axis. In the crystal, the water molecules link the dimers into infinite chains along the b axis via O—H···Br and C—H···O interactions.

Related literature top

For the structures of some similar doubly bridged copper(II) complexes, see: Li et al. (2000); Rigamonti et al. (2008); Suo (2008). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984).

Experimental top

A solution of 2-acetylpyridine (0.20 g, 1.65 mmol) and N,N-dimethylethyldiamine (0.14 g, 1.65 mmol) in ethanol (20 ml) was stirred at reflux for 2 hr. Then, a solution of copper (I) bromide (0.21 g, 1.65 mmol) in a minimum amount of ethanol was added. The resulting mixture was refluxed for 30 min, and then left at room temperature. The crystals of the title complex were obtained in a few days.

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: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: ' = -x, y, -z + 1/2.

Bis(µ-2-{1-[2-(dimethylamino)ethylimino]ethyl}phenolato)bis[bromidocopper(II)] monohydrate top

Crystal data top

[Cu₂Br₂(C₁₂H₁₇N2O)₂]·H₂O	F(000) = 1440
M_r = 715.47	D_x = 1.722 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3159 reflections
a = 20.754 (4) Å	θ = 2.4–30.5°
b = 8.2492 (16) Å	µ = 4.47 mm⁻¹
c = 18.521 (4) Å	T = 100 K
β = 119.528 (2)°	Block, green
V = 2759.1 (9) Å³	0.19 × 0.14 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3007 independent reflections
Radiation source: fine-focus sealed tube	2623 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
T_min = 0.484, T_max = 0.689	k = −10→10
10414 measured reflections	l = −21→23

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0216P)² + 1.9328P] where P = (F_o² + 2F_c²)/3
3007 reflections	(Δ/σ)_max = 0.001
165 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Cu₂Br₂(C₁₂H₁₇N2O)₂]·H₂O	V = 2759.1 (9) Å³
M_r = 715.47	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 20.754 (4) Å	µ = 4.47 mm⁻¹
b = 8.2492 (16) Å	T = 100 K
c = 18.521 (4) Å	0.19 × 0.14 × 0.09 mm
β = 119.528 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3007 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2623 reflections with I > 2σ(I)
T_min = 0.484, T_max = 0.689	R_int = 0.042
10414 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	1 restraint
wR(F²) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.36 e Å⁻³
3007 reflections	Δρ_min = −0.51 e Å⁻³
165 parameters

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	0.073508 (14)	0.69663 (3)	0.253261 (16)	0.01063 (8)
Br1	0.150450 (12)	0.94932 (3)	0.260812 (15)	0.01679 (8)
O1	0.03282 (8)	0.75649 (19)	0.32448 (10)	0.0119 (3)
N1	0.14514 (10)	0.5556 (2)	0.34424 (12)	0.0137 (4)
N2	0.08944 (10)	0.5480 (2)	0.17527 (12)	0.0152 (4)
C1	0.07547 (12)	0.7880 (3)	0.40514 (14)	0.0117 (4)
C2	0.05469 (13)	0.9126 (3)	0.44099 (15)	0.0168 (5)
H2	0.0119	0.9756	0.4073	0.020*
C3	0.09599 (13)	0.9446 (3)	0.52491 (16)	0.0196 (5)
H3	0.0810	1.0287	0.5484	0.024*
C4	0.15940 (13)	0.8552 (3)	0.57543 (15)	0.0190 (5)
H4	0.1875	0.8778	0.6331	0.023*
C5	0.18105 (12)	0.7334 (3)	0.54092 (15)	0.0167 (5)
H5	0.2246	0.6732	0.5755	0.020*
C6	0.14031 (12)	0.6961 (3)	0.45577 (14)	0.0124 (5)
C7	0.16441 (12)	0.5626 (3)	0.42169 (15)	0.0145 (5)
C8	0.21248 (14)	0.4320 (3)	0.48106 (17)	0.0226 (6)
H8A	0.1951	0.3254	0.4554	0.034*
H8B	0.2096	0.4381	0.5322	0.034*
H8C	0.2639	0.4476	0.4941	0.034*
C9	0.17044 (13)	0.4215 (3)	0.31143 (16)	0.0188 (5)
H9A	0.1396	0.3240	0.3026	0.023*
H9B	0.2225	0.3938	0.3514	0.023*
C10	0.16385 (13)	0.4758 (3)	0.23030 (16)	0.0185 (5)
H10A	0.2027	0.5571	0.2412	0.022*
H10B	0.1716	0.3820	0.2021	0.022*
C11	0.03162 (13)	0.4203 (3)	0.14254 (16)	0.0194 (5)
H11A	−0.0164	0.4691	0.1044	0.029*
H11B	0.0290	0.3688	0.1887	0.029*
H11C	0.0441	0.3386	0.1130	0.029*
C12	0.09097 (15)	0.6276 (3)	0.10441 (16)	0.0221 (6)
H12A	0.1035	0.5475	0.0742	0.033*
H12B	0.1282	0.7140	0.1251	0.033*
H12C	0.0422	0.6741	0.0670	0.033*
O2	0.0000	1.1437 (3)	0.2500	0.0347 (7)
H2O	0.0349 (14)	1.085 (3)	0.257 (2)	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.00875 (14)	0.01254 (15)	0.01042 (16)	0.00081 (10)	0.00458 (12)	−0.00042 (11)
Br1	0.01330 (12)	0.01715 (13)	0.01898 (14)	−0.00367 (9)	0.00723 (10)	0.00097 (9)
O1	0.0089 (7)	0.0168 (8)	0.0090 (8)	0.0009 (6)	0.0035 (6)	−0.0008 (6)
N1	0.0113 (9)	0.0135 (10)	0.0164 (11)	0.0011 (8)	0.0069 (8)	0.0003 (8)
N2	0.0124 (9)	0.0188 (11)	0.0146 (11)	0.0004 (8)	0.0068 (8)	−0.0015 (8)
C1	0.0090 (10)	0.0151 (12)	0.0110 (11)	−0.0012 (9)	0.0050 (9)	−0.0005 (9)
C2	0.0143 (11)	0.0203 (12)	0.0152 (13)	0.0019 (9)	0.0068 (10)	−0.0009 (10)
C3	0.0194 (12)	0.0242 (14)	0.0182 (13)	−0.0022 (10)	0.0114 (11)	−0.0063 (11)
C4	0.0176 (12)	0.0292 (14)	0.0099 (12)	−0.0067 (10)	0.0066 (10)	−0.0032 (10)
C5	0.0109 (11)	0.0228 (13)	0.0144 (13)	−0.0012 (9)	0.0047 (10)	0.0042 (10)
C6	0.0114 (10)	0.0149 (11)	0.0122 (12)	−0.0020 (9)	0.0068 (9)	0.0014 (9)
C7	0.0088 (10)	0.0151 (12)	0.0184 (13)	0.0003 (9)	0.0057 (10)	0.0037 (10)
C8	0.0238 (13)	0.0204 (14)	0.0224 (14)	0.0074 (11)	0.0105 (12)	0.0074 (11)
C9	0.0161 (12)	0.0170 (12)	0.0203 (13)	0.0050 (10)	0.0067 (11)	−0.0038 (10)
C10	0.0122 (11)	0.0230 (13)	0.0192 (14)	0.0031 (10)	0.0068 (10)	−0.0043 (11)
C11	0.0172 (12)	0.0189 (13)	0.0200 (13)	−0.0019 (10)	0.0075 (11)	−0.0063 (10)
C12	0.0251 (13)	0.0281 (14)	0.0180 (14)	0.0015 (11)	0.0144 (11)	−0.0019 (11)
O2	0.0404 (18)	0.0183 (15)	0.059 (2)	0.000	0.0349 (17)	0.000

Geometric parameters (Å, º) top

Cu1—O1	1.9480 (15)	C5—C6	1.408 (3)
Cu1—N1	1.983 (2)	C5—H5	0.9500
Cu1—O1ⁱ	2.0138 (15)	C6—C7	1.474 (3)
Cu1—N2	2.042 (2)	C7—C8	1.512 (3)
Cu1—Br1	2.5874 (5)	C8—H8A	0.9800
O1—C1	1.334 (3)	C8—H8B	0.9800
O1—Cu1ⁱ	2.0138 (15)	C8—H8C	0.9800
N1—C7	1.287 (3)	C9—C10	1.508 (4)
N1—C9	1.478 (3)	C9—H9A	0.9900
N2—C12	1.482 (3)	C9—H9B	0.9900
N2—C11	1.483 (3)	C10—H10A	0.9900
N2—C10	1.492 (3)	C10—H10B	0.9900
C1—C2	1.402 (3)	C11—H11A	0.9800
C1—C6	1.422 (3)	C11—H11B	0.9800
C2—C3	1.381 (3)	C11—H11C	0.9800
C2—H2	0.9500	C12—H12A	0.9800
C3—C4	1.392 (4)	C12—H12B	0.9800
C3—H3	0.9500	C12—H12C	0.9800
C4—C5	1.379 (3)	O2—H2O	0.827 (17)
C4—H4	0.9500

O1—Cu1—N1	88.11 (7)	C5—C6—C1	118.2 (2)
O1—Cu1—O1ⁱ	74.57 (7)	C5—C6—C7	120.0 (2)
N1—Cu1—O1ⁱ	148.18 (7)	C1—C6—C7	121.8 (2)
O1—Cu1—N2	155.03 (7)	N1—C7—C6	121.8 (2)
N1—Cu1—N2	86.20 (8)	N1—C7—C8	120.7 (2)
O1ⁱ—Cu1—N2	98.28 (7)	C6—C7—C8	117.6 (2)
O1—Cu1—Br1	102.77 (5)	C7—C8—H8A	109.5
N1—Cu1—Br1	104.03 (6)	C7—C8—H8B	109.5
O1ⁱ—Cu1—Br1	105.71 (5)	H8A—C8—H8B	109.5
N2—Cu1—Br1	102.19 (6)	C7—C8—H8C	109.5
C1—O1—Cu1	122.55 (13)	H8A—C8—H8C	109.5
C1—O1—Cu1ⁱ	137.48 (13)	H8B—C8—H8C	109.5
Cu1—O1—Cu1ⁱ	98.14 (7)	N1—C9—C10	108.1 (2)
C7—N1—C9	120.9 (2)	N1—C9—H9A	110.1
C7—N1—Cu1	127.71 (16)	C10—C9—H9A	110.1
C9—N1—Cu1	111.06 (15)	N1—C9—H9B	110.1
C12—N2—C11	108.61 (19)	C10—C9—H9B	110.1
C12—N2—C10	108.36 (18)	H9A—C9—H9B	108.4
C11—N2—C10	110.64 (19)	N2—C10—C9	110.74 (18)
C12—N2—Cu1	116.21 (15)	N2—C10—H10A	109.5
C11—N2—Cu1	109.58 (14)	C9—C10—H10A	109.5
C10—N2—Cu1	103.31 (14)	N2—C10—H10B	109.5
O1—C1—C2	118.9 (2)	C9—C10—H10B	109.5
O1—C1—C6	121.6 (2)	H10A—C10—H10B	108.1
C2—C1—C6	119.4 (2)	N2—C11—H11A	109.5
C3—C2—C1	120.5 (2)	N2—C11—H11B	109.5
C3—C2—H2	119.7	H11A—C11—H11B	109.5
C1—C2—H2	119.7	N2—C11—H11C	109.5
C2—C3—C4	120.8 (2)	H11A—C11—H11C	109.5
C2—C3—H3	119.6	H11B—C11—H11C	109.5
C4—C3—H3	119.6	N2—C12—H12A	109.5
C5—C4—C3	119.4 (2)	N2—C12—H12B	109.5
C5—C4—H4	120.3	H12A—C12—H12B	109.5
C3—C4—H4	120.3	N2—C12—H12C	109.5
C4—C5—C6	121.7 (2)	H12A—C12—H12C	109.5
C4—C5—H5	119.1	H12B—C12—H12C	109.5
C6—C5—H5	119.1

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱⁱ	0.98	2.40	3.299 (3)	152
O2—H2O···Br1	0.83 (2)	2.62 (2)	3.4269 (14)	167 (3)

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Cu₂Br₂(C₁₂H₁₇N2O)₂]·H₂O
M_r	715.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	20.754 (4), 8.2492 (16), 18.521 (4)
β (°)	119.528 (2)
V (Å³)	2759.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.47
Crystal size (mm)	0.19 × 0.14 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.484, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	10414, 3007, 2623
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.060, 1.05
No. of reflections	3007
No. of parameters	165
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)	0.36, −0.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001; Atwood & Barbour, 2003), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.98	2.40	3.299 (3)	152
O2—H2O···Br1	0.827 (17)	2.617 (18)	3.4269 (14)	167 (3)

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP004/2010B).

References

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

Bis(μ-2-{1-[2-(di­methyl­amino)­ethyl­imino]­eth­yl}phenolato)bis­­[bromido­copper(II)] monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(μ-2-{1-[2-(dimethylamino)ethylimino]ethyl}phenolato)bis[bromidocopper(II)] monohydrate