Bromido(2-{1-[2-(piperidin-1-yl)ethyl­imino]­eth­yl}phenolato)copper(II)

Zhao, X.-F.; Li, F.

doi:10.1107/S1600536810026711

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m913

https://doi.org/10.1107/S1600536810026711

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Bromido(2-{1-[2-(piperidin-1-yl)ethylimino]ethyl}phenolato)copper(II)

Xiao-Fan Zhao ^a and Fang Li ^a ^*

^aCollege of Chemistry & Chemical Engineering, Shaoxing University, Shaoxing 312000, People's Republic of China
^*Correspondence e-mail: xiaofan_zhao@126.com

(Received 5 July 2010; accepted 6 July 2010; online 10 July 2010)

In the title complex, [CuBr(C₁₅H₂₁N₂O)], the Cu^II atom is coordinated by one phenolate O, one imine N and one amine N atom of the tridentate Schiff base ligand and by one bromide ion, resulting in a distorted CuBrN₂O square-planar geometry for the metal ion, with the N atoms in a cis conformation.

Related literature

For a related structure and background references, see the preceding paper: Zhao & Li (2010 ).

Experimental

Crystal data

[CuBr(C₁₅H₂₁N₂O)]
M_r = 388.79
Monoclinic, P 2₁ /c
a = 10.988 (3) Å
b = 17.181 (5) Å
c = 8.173 (2) Å
β = 92.366 (3)°
V = 1541.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 4.01 mm⁻¹
T = 298 K
0.27 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.411, T_max = 0.459
9503 measured reflections
3357 independent reflections
2373 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.084
S = 1.06
3357 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O1	1.872 (3)
Cu1—N1	1.954 (3)
Cu1—N2	2.034 (3)
Cu1—Br1	2.4030 (7)

O1—Cu1—N1	91.04 (11)
O1—Cu1—N2	162.99 (11)
N1—Cu1—N2	86.20 (11)
O1—Cu1—Br1	92.26 (8)
N1—Cu1—Br1	159.19 (8)
N2—Cu1—Br1	96.27 (8)

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810026711/hb5544sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026711/hb5544Isup2.hkl

checkCIF report

Related literature top

For a related structure and background references, see the preceding paper: Zhao & Li (2010).

Experimental top

1-(2-Hydroxyphenyl)ethanone (1 mmol, 136 mg), 2-piperidin-1-ylethylamine (1 mmol, 128 mg), and copper(II) bromide (1 mmol, 223 mg) were dissolved in methanol (80 ml). The mixture was stirred at room temperature for 1 h to give a blue solution. The resulting solution was kept in air for a few days, and blue blocks of (I) were formed.

Structure description top

For a related structure and background references, see the preceding paper: Zhao & Li (2010).

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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title complex, showing 30% displacement ellipsoids (arbitrary spheres for the H atoms).

Bromido(2-{1-[2-(piperidin-1-yl)ethylimino]ethyl}phenolato)copper(II) top

Crystal data top

[CuBr(C₁₅H₂₁N₂O)]	F(000) = 788
M_r = 388.79	D_x = 1.675 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2701 reflections
a = 10.988 (3) Å	θ = 2.3–26.3°
b = 17.181 (5) Å	µ = 4.01 mm⁻¹
c = 8.173 (2) Å	T = 298 K
β = 92.366 (3)°	Block, blue
V = 1541.6 (7) Å³	0.27 × 0.23 × 0.23 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3357 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→14
T_min = 0.411, T_max = 0.459	k = −21→21
9503 measured reflections	l = −7→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0318P)² + 0.4765P] where P = (F_o² + 2F_c²)/3
3357 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[CuBr(C₁₅H₂₁N₂O)]	V = 1541.6 (7) Å³
M_r = 388.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.988 (3) Å	µ = 4.01 mm⁻¹
b = 17.181 (5) Å	T = 298 K
c = 8.173 (2) Å	0.27 × 0.23 × 0.23 mm
β = 92.366 (3)°

Data collection top

Bruker SMART CCD diffractometer	3357 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2373 reflections with I > 2σ(I)
T_min = 0.411, T_max = 0.459	R_int = 0.044
9503 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
3357 reflections	Δρ_min = −0.49 e Å⁻³
182 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	0.50444 (4)	0.13785 (2)	0.50364 (5)	0.02851 (12)
N1	0.6334 (3)	0.12175 (16)	0.3495 (3)	0.0315 (7)
N2	0.3861 (2)	0.12461 (14)	0.3077 (3)	0.0257 (6)
O1	0.6161 (2)	0.17983 (15)	0.6586 (3)	0.0441 (7)
Br1	0.36084 (4)	0.10855 (2)	0.70885 (4)	0.04276 (13)
C1	0.8014 (3)	0.13107 (19)	0.5452 (4)	0.0327 (8)
C2	0.7327 (3)	0.16805 (19)	0.6674 (4)	0.0318 (8)
C3	0.7973 (4)	0.1946 (2)	0.8102 (5)	0.0428 (9)
H3	0.7548	0.2208	0.8895	0.051*
C4	0.9194 (4)	0.1831 (2)	0.8359 (5)	0.0514 (11)
H4	0.9586	0.2013	0.9314	0.062*
C5	0.9849 (4)	0.1445 (3)	0.7204 (6)	0.0580 (12)
H5	1.0677	0.1355	0.7386	0.070*
C6	0.9266 (3)	0.1197 (2)	0.5789 (5)	0.0498 (11)
H6	0.9717	0.0942	0.5015	0.060*
C7	0.7472 (3)	0.1122 (2)	0.3834 (4)	0.0333 (8)
C8	0.8306 (4)	0.0842 (3)	0.2529 (5)	0.0555 (12)
H8A	0.7826	0.0659	0.1599	0.083*
H8B	0.8807	0.0426	0.2959	0.083*
H8C	0.8815	0.1264	0.2202	0.083*
C9	0.5824 (3)	0.1139 (2)	0.1796 (4)	0.0401 (9)
H9A	0.5748	0.0594	0.1503	0.048*
H9B	0.6357	0.1388	0.1038	0.048*
C10	0.4607 (3)	0.1519 (2)	0.1714 (4)	0.0354 (9)
H10A	0.4705	0.2079	0.1781	0.042*
H10B	0.4192	0.1397	0.0675	0.042*
C11	0.2726 (3)	0.1720 (2)	0.3175 (4)	0.0365 (9)
H11A	0.2943	0.2267	0.3228	0.044*
H11B	0.2327	0.1589	0.4174	0.044*
C12	0.1837 (4)	0.1588 (2)	0.1714 (5)	0.0478 (10)
H12A	0.1102	0.1888	0.1863	0.057*
H12B	0.2202	0.1769	0.0722	0.057*
C13	0.1513 (4)	0.0739 (3)	0.1531 (5)	0.0514 (11)
H13A	0.1009	0.0664	0.0542	0.062*
H13B	0.1050	0.0574	0.2455	0.062*
C14	0.2659 (3)	0.0248 (2)	0.1448 (4)	0.0368 (9)
H14A	0.2440	−0.0299	0.1429	0.044*
H14B	0.3066	0.0365	0.0446	0.044*
C15	0.3516 (3)	0.04072 (19)	0.2906 (4)	0.0300 (8)
H15A	0.3132	0.0240	0.3895	0.036*
H15B	0.4250	0.0100	0.2801	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0263 (2)	0.0346 (2)	0.0246 (2)	0.00112 (18)	0.00036 (16)	−0.00404 (17)
N1	0.0309 (18)	0.0366 (17)	0.0272 (16)	−0.0056 (12)	0.0035 (12)	−0.0042 (12)
N2	0.0262 (16)	0.0254 (15)	0.0255 (15)	0.0003 (11)	0.0006 (11)	0.0015 (11)
O1	0.0312 (15)	0.0577 (17)	0.0430 (16)	0.0065 (12)	−0.0044 (11)	−0.0243 (13)
Br1	0.0439 (3)	0.0565 (3)	0.0286 (2)	0.00307 (19)	0.00991 (16)	0.00076 (18)
C1	0.031 (2)	0.0294 (18)	0.037 (2)	−0.0027 (15)	−0.0023 (15)	0.0009 (15)
C2	0.032 (2)	0.0254 (17)	0.038 (2)	−0.0024 (15)	−0.0060 (15)	−0.0011 (16)
C3	0.053 (3)	0.033 (2)	0.041 (2)	−0.0026 (18)	−0.0108 (18)	−0.0011 (17)
C4	0.047 (3)	0.053 (3)	0.052 (3)	−0.011 (2)	−0.025 (2)	0.008 (2)
C5	0.038 (3)	0.072 (3)	0.062 (3)	−0.001 (2)	−0.016 (2)	0.011 (3)
C6	0.032 (2)	0.056 (3)	0.062 (3)	0.0000 (18)	0.001 (2)	0.006 (2)
C7	0.023 (2)	0.0343 (19)	0.044 (2)	−0.0033 (15)	0.0089 (16)	−0.0029 (16)
C8	0.032 (2)	0.083 (3)	0.052 (3)	0.000 (2)	0.0083 (19)	−0.019 (2)
C9	0.033 (2)	0.059 (2)	0.029 (2)	−0.0121 (18)	0.0057 (16)	−0.0005 (18)
C10	0.037 (2)	0.041 (2)	0.0274 (19)	−0.0124 (17)	0.0010 (15)	0.0044 (16)
C11	0.037 (2)	0.034 (2)	0.039 (2)	0.0100 (16)	0.0004 (16)	−0.0004 (17)
C12	0.038 (2)	0.058 (3)	0.047 (2)	0.018 (2)	−0.0096 (18)	0.003 (2)
C13	0.036 (2)	0.074 (3)	0.043 (2)	−0.011 (2)	−0.0067 (18)	0.005 (2)
C14	0.042 (2)	0.036 (2)	0.033 (2)	−0.0079 (17)	0.0008 (16)	−0.0017 (16)
C15	0.034 (2)	0.0250 (18)	0.0307 (19)	0.0006 (15)	0.0042 (15)	0.0024 (15)

Geometric parameters (Å, º) top

Cu1—O1	1.872 (3)	C8—H8A	0.9600
Cu1—N1	1.954 (3)	C8—H8B	0.9600
Cu1—N2	2.034 (3)	C8—H8C	0.9600
Cu1—Br1	2.4030 (7)	C9—C10	1.487 (5)
N1—C7	1.281 (4)	C9—H9A	0.9700
N1—C9	1.482 (5)	C9—H9B	0.9700
N2—C10	1.485 (4)	C10—H10A	0.9700
N2—C11	1.493 (4)	C10—H10B	0.9700
N2—C15	1.495 (4)	C11—C12	1.528 (5)
O1—C2	1.296 (4)	C11—H11A	0.9700
C1—C6	1.405 (5)	C11—H11B	0.9700
C1—C2	1.425 (5)	C12—C13	1.508 (6)
C1—C7	1.464 (5)	C12—H12A	0.9700
C2—C3	1.417 (5)	C12—H12B	0.9700
C3—C4	1.364 (5)	C13—C14	1.520 (5)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.380 (6)	C13—H13B	0.9700
C4—H4	0.9300	C14—C15	1.513 (5)
C5—C6	1.366 (6)	C14—H14A	0.9700
C5—H5	0.9300	C14—H14B	0.9700
C6—H6	0.9300	C15—H15A	0.9700
C7—C8	1.512 (5)	C15—H15B	0.9700

O1—Cu1—N1	91.04 (11)	N1—C9—C10	107.9 (3)
O1—Cu1—N2	162.99 (11)	N1—C9—H9A	110.1
N1—Cu1—N2	86.20 (11)	C10—C9—H9A	110.1
O1—Cu1—Br1	92.26 (8)	N1—C9—H9B	110.1
N1—Cu1—Br1	159.19 (8)	C10—C9—H9B	110.1
N2—Cu1—Br1	96.27 (8)	H9A—C9—H9B	108.4
C7—N1—C9	121.3 (3)	N2—C10—C9	110.6 (3)
C7—N1—Cu1	127.4 (2)	N2—C10—H10A	109.5
C9—N1—Cu1	111.1 (2)	C9—C10—H10A	109.5
C10—N2—C11	110.8 (3)	N2—C10—H10B	109.5
C10—N2—C15	112.3 (2)	C9—C10—H10B	109.5
C11—N2—C15	108.8 (3)	H10A—C10—H10B	108.1
C10—N2—Cu1	101.6 (2)	N2—C11—C12	112.7 (3)
C11—N2—Cu1	113.9 (2)	N2—C11—H11A	109.1
C15—N2—Cu1	109.4 (2)	C12—C11—H11A	109.1
C2—O1—Cu1	126.6 (2)	N2—C11—H11B	109.1
C6—C1—C2	117.8 (3)	C12—C11—H11B	109.1
C6—C1—C7	120.3 (3)	H11A—C11—H11B	107.8
C2—C1—C7	121.6 (3)	C13—C12—C11	111.2 (3)
O1—C2—C3	117.1 (3)	C13—C12—H12A	109.4
O1—C2—C1	125.6 (3)	C11—C12—H12A	109.4
C3—C2—C1	117.4 (3)	C13—C12—H12B	109.4
C4—C3—C2	122.4 (4)	C11—C12—H12B	109.4
C4—C3—H3	118.8	H12A—C12—H12B	108.0
C2—C3—H3	118.8	C12—C13—C14	110.4 (3)
C3—C4—C5	120.1 (4)	C12—C13—H13A	109.6
C3—C4—H4	119.9	C14—C13—H13A	109.6
C5—C4—H4	119.9	C12—C13—H13B	109.6
C6—C5—C4	119.3 (4)	C14—C13—H13B	109.6
C6—C5—H5	120.4	H13A—C13—H13B	108.1
C4—C5—H5	120.4	C15—C14—C13	110.7 (3)
C5—C6—C1	122.9 (4)	C15—C14—H14A	109.5
C5—C6—H6	118.5	C13—C14—H14A	109.5
C1—C6—H6	118.5	C15—C14—H14B	109.5
N1—C7—C1	121.6 (3)	C13—C14—H14B	109.5
N1—C7—C8	120.2 (3)	H14A—C14—H14B	108.1
C1—C7—C8	118.2 (3)	N2—C15—C14	113.3 (3)
C7—C8—H8A	109.5	N2—C15—H15A	108.9
C7—C8—H8B	109.5	C14—C15—H15A	108.9
H8A—C8—H8B	109.5	N2—C15—H15B	108.9
C7—C8—H8C	109.5	C14—C15—H15B	108.9
H8A—C8—H8C	109.5	H15A—C15—H15B	107.7
H8B—C8—H8C	109.5

Experimental details

Crystal data
Chemical formula	[CuBr(C₁₅H₂₁N₂O)]
M_r	388.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.988 (3), 17.181 (5), 8.173 (2)
β (°)	92.366 (3)
V (Å³)	1541.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.01
Crystal size (mm)	0.27 × 0.23 × 0.23

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.411, 0.459
No. of measured, independent and observed [I > 2σ(I)] reflections	9503, 3357, 2373
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 1.06
No. of reflections	3357
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.49

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

Selected geometric parameters (Å, º) top

Cu1—O1	1.872 (3)	Cu1—N2	2.034 (3)
Cu1—N1	1.954 (3)	Cu1—Br1	2.4030 (7)

O1—Cu1—N1	91.04 (11)	O1—Cu1—Br1	92.26 (8)
O1—Cu1—N2	162.99 (11)	N1—Cu1—Br1	159.19 (8)
N1—Cu1—N2	86.20 (11)	N2—Cu1—Br1	96.27 (8)

Acknowledgements

Financial support from the Shaoxing University research fund is gratefully acknowledged.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, X.-F. & Li, F. (2010). Acta Cryst. E66, m912. Web of Science CSD CrossRef IUCr Journals Google Scholar