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

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ISSN: 2056-9890

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

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 CuII 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[Zhao, X.-F. & Li, F. (2010). Acta Cryst. E66, m912.]).

[Scheme 1]

Experimental

Crystal data
  • [CuBr(C15H21N2O)]

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.411, Tmax = 0.459

  • 9503 measured reflections

  • 3357 independent reflections

  • 2373 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.084

  • S = 1.06

  • 3357 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −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[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).

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
[Figure 1] 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
Mr = 388.79Dx = 1.675 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2701 reflections
a = 10.988 (3) Åθ = 2.3–26.3°
b = 17.181 (5) ŵ = 4.01 mm1
c = 8.173 (2) ÅT = 298 K
β = 92.366 (3)°Block, blue
V = 1541.6 (7) Å30.27 × 0.23 × 0.23 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
3357 independent reflections
Radiation source: fine-focus sealed tube2373 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1214
Tmin = 0.411, Tmax = 0.459k = 2121
9503 measured reflectionsl = 710
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0318P)2 + 0.4765P]
where P = (Fo2 + 2Fc2)/3
3357 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
[CuBr(C15H21N2O)]V = 1541.6 (7) Å3
Mr = 388.79Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.988 (3) ŵ = 4.01 mm1
b = 17.181 (5) ÅT = 298 K
c = 8.173 (2) Å0.27 × 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)
Tmin = 0.411, Tmax = 0.459Rint = 0.044
9503 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.06Δρmax = 0.40 e Å3
3357 reflectionsΔρmin = 0.49 e Å3
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
xyzUiso*/Ueq
Cu10.50444 (4)0.13785 (2)0.50364 (5)0.02851 (12)
N10.6334 (3)0.12175 (16)0.3495 (3)0.0315 (7)
N20.3861 (2)0.12461 (14)0.3077 (3)0.0257 (6)
O10.6161 (2)0.17983 (15)0.6586 (3)0.0441 (7)
Br10.36084 (4)0.10855 (2)0.70885 (4)0.04276 (13)
C10.8014 (3)0.13107 (19)0.5452 (4)0.0327 (8)
C20.7327 (3)0.16805 (19)0.6674 (4)0.0318 (8)
C30.7973 (4)0.1946 (2)0.8102 (5)0.0428 (9)
H30.75480.22080.88950.051*
C40.9194 (4)0.1831 (2)0.8359 (5)0.0514 (11)
H40.95860.20130.93140.062*
C50.9849 (4)0.1445 (3)0.7204 (6)0.0580 (12)
H51.06770.13550.73860.070*
C60.9266 (3)0.1197 (2)0.5789 (5)0.0498 (11)
H60.97170.09420.50150.060*
C70.7472 (3)0.1122 (2)0.3834 (4)0.0333 (8)
C80.8306 (4)0.0842 (3)0.2529 (5)0.0555 (12)
H8A0.78260.06590.15990.083*
H8B0.88070.04260.29590.083*
H8C0.88150.12640.22020.083*
C90.5824 (3)0.1139 (2)0.1796 (4)0.0401 (9)
H9A0.57480.05940.15030.048*
H9B0.63570.13880.10380.048*
C100.4607 (3)0.1519 (2)0.1714 (4)0.0354 (9)
H10A0.47050.20790.17810.042*
H10B0.41920.13970.06750.042*
C110.2726 (3)0.1720 (2)0.3175 (4)0.0365 (9)
H11A0.29430.22670.32280.044*
H11B0.23270.15890.41740.044*
C120.1837 (4)0.1588 (2)0.1714 (5)0.0478 (10)
H12A0.11020.18880.18630.057*
H12B0.22020.17690.07220.057*
C130.1513 (4)0.0739 (3)0.1531 (5)0.0514 (11)
H13A0.10090.06640.05420.062*
H13B0.10500.05740.24550.062*
C140.2659 (3)0.0248 (2)0.1448 (4)0.0368 (9)
H14A0.24400.02990.14290.044*
H14B0.30660.03650.04460.044*
C150.3516 (3)0.04072 (19)0.2906 (4)0.0300 (8)
H15A0.31320.02400.38950.036*
H15B0.42500.01000.28010.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0263 (2)0.0346 (2)0.0246 (2)0.00112 (18)0.00036 (16)0.00404 (17)
N10.0309 (18)0.0366 (17)0.0272 (16)0.0056 (12)0.0035 (12)0.0042 (12)
N20.0262 (16)0.0254 (15)0.0255 (15)0.0003 (11)0.0006 (11)0.0015 (11)
O10.0312 (15)0.0577 (17)0.0430 (16)0.0065 (12)0.0044 (11)0.0243 (13)
Br10.0439 (3)0.0565 (3)0.0286 (2)0.00307 (19)0.00991 (16)0.00076 (18)
C10.031 (2)0.0294 (18)0.037 (2)0.0027 (15)0.0023 (15)0.0009 (15)
C20.032 (2)0.0254 (17)0.038 (2)0.0024 (15)0.0060 (15)0.0011 (16)
C30.053 (3)0.033 (2)0.041 (2)0.0026 (18)0.0108 (18)0.0011 (17)
C40.047 (3)0.053 (3)0.052 (3)0.011 (2)0.025 (2)0.008 (2)
C50.038 (3)0.072 (3)0.062 (3)0.001 (2)0.016 (2)0.011 (3)
C60.032 (2)0.056 (3)0.062 (3)0.0000 (18)0.001 (2)0.006 (2)
C70.023 (2)0.0343 (19)0.044 (2)0.0033 (15)0.0089 (16)0.0029 (16)
C80.032 (2)0.083 (3)0.052 (3)0.000 (2)0.0083 (19)0.019 (2)
C90.033 (2)0.059 (2)0.029 (2)0.0121 (18)0.0057 (16)0.0005 (18)
C100.037 (2)0.041 (2)0.0274 (19)0.0124 (17)0.0010 (15)0.0044 (16)
C110.037 (2)0.034 (2)0.039 (2)0.0100 (16)0.0004 (16)0.0004 (17)
C120.038 (2)0.058 (3)0.047 (2)0.018 (2)0.0096 (18)0.003 (2)
C130.036 (2)0.074 (3)0.043 (2)0.011 (2)0.0067 (18)0.005 (2)
C140.042 (2)0.036 (2)0.033 (2)0.0079 (17)0.0008 (16)0.0017 (16)
C150.034 (2)0.0250 (18)0.0307 (19)0.0006 (15)0.0042 (15)0.0024 (15)
Geometric parameters (Å, º) top
Cu1—O11.872 (3)C8—H8A0.9600
Cu1—N11.954 (3)C8—H8B0.9600
Cu1—N22.034 (3)C8—H8C0.9600
Cu1—Br12.4030 (7)C9—C101.487 (5)
N1—C71.281 (4)C9—H9A0.9700
N1—C91.482 (5)C9—H9B0.9700
N2—C101.485 (4)C10—H10A0.9700
N2—C111.493 (4)C10—H10B0.9700
N2—C151.495 (4)C11—C121.528 (5)
O1—C21.296 (4)C11—H11A0.9700
C1—C61.405 (5)C11—H11B0.9700
C1—C21.425 (5)C12—C131.508 (6)
C1—C71.464 (5)C12—H12A0.9700
C2—C31.417 (5)C12—H12B0.9700
C3—C41.364 (5)C13—C141.520 (5)
C3—H30.9300C13—H13A0.9700
C4—C51.380 (6)C13—H13B0.9700
C4—H40.9300C14—C151.513 (5)
C5—C61.366 (6)C14—H14A0.9700
C5—H50.9300C14—H14B0.9700
C6—H60.9300C15—H15A0.9700
C7—C81.512 (5)C15—H15B0.9700
O1—Cu1—N191.04 (11)N1—C9—C10107.9 (3)
O1—Cu1—N2162.99 (11)N1—C9—H9A110.1
N1—Cu1—N286.20 (11)C10—C9—H9A110.1
O1—Cu1—Br192.26 (8)N1—C9—H9B110.1
N1—Cu1—Br1159.19 (8)C10—C9—H9B110.1
N2—Cu1—Br196.27 (8)H9A—C9—H9B108.4
C7—N1—C9121.3 (3)N2—C10—C9110.6 (3)
C7—N1—Cu1127.4 (2)N2—C10—H10A109.5
C9—N1—Cu1111.1 (2)C9—C10—H10A109.5
C10—N2—C11110.8 (3)N2—C10—H10B109.5
C10—N2—C15112.3 (2)C9—C10—H10B109.5
C11—N2—C15108.8 (3)H10A—C10—H10B108.1
C10—N2—Cu1101.6 (2)N2—C11—C12112.7 (3)
C11—N2—Cu1113.9 (2)N2—C11—H11A109.1
C15—N2—Cu1109.4 (2)C12—C11—H11A109.1
C2—O1—Cu1126.6 (2)N2—C11—H11B109.1
C6—C1—C2117.8 (3)C12—C11—H11B109.1
C6—C1—C7120.3 (3)H11A—C11—H11B107.8
C2—C1—C7121.6 (3)C13—C12—C11111.2 (3)
O1—C2—C3117.1 (3)C13—C12—H12A109.4
O1—C2—C1125.6 (3)C11—C12—H12A109.4
C3—C2—C1117.4 (3)C13—C12—H12B109.4
C4—C3—C2122.4 (4)C11—C12—H12B109.4
C4—C3—H3118.8H12A—C12—H12B108.0
C2—C3—H3118.8C12—C13—C14110.4 (3)
C3—C4—C5120.1 (4)C12—C13—H13A109.6
C3—C4—H4119.9C14—C13—H13A109.6
C5—C4—H4119.9C12—C13—H13B109.6
C6—C5—C4119.3 (4)C14—C13—H13B109.6
C6—C5—H5120.4H13A—C13—H13B108.1
C4—C5—H5120.4C15—C14—C13110.7 (3)
C5—C6—C1122.9 (4)C15—C14—H14A109.5
C5—C6—H6118.5C13—C14—H14A109.5
C1—C6—H6118.5C15—C14—H14B109.5
N1—C7—C1121.6 (3)C13—C14—H14B109.5
N1—C7—C8120.2 (3)H14A—C14—H14B108.1
C1—C7—C8118.2 (3)N2—C15—C14113.3 (3)
C7—C8—H8A109.5N2—C15—H15A108.9
C7—C8—H8B109.5C14—C15—H15A108.9
H8A—C8—H8B109.5N2—C15—H15B108.9
C7—C8—H8C109.5C14—C15—H15B108.9
H8A—C8—H8C109.5H15A—C15—H15B107.7
H8B—C8—H8C109.5

Experimental details

Crystal data
Chemical formula[CuBr(C15H21N2O)]
Mr388.79
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)10.988 (3), 17.181 (5), 8.173 (2)
β (°) 92.366 (3)
V3)1541.6 (7)
Z4
Radiation typeMo Kα
µ (mm1)4.01
Crystal size (mm)0.27 × 0.23 × 0.23
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.411, 0.459
No. of measured, independent and
observed [I > 2σ(I)] reflections
9503, 3357, 2373
Rint0.044
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.084, 1.06
No. of reflections3357
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—O11.872 (3)Cu1—N22.034 (3)
Cu1—N11.954 (3)Cu1—Br12.4030 (7)
O1—Cu1—N191.04 (11)O1—Cu1—Br192.26 (8)
O1—Cu1—N2162.99 (11)N1—Cu1—Br1159.19 (8)
N1—Cu1—N286.20 (11)N2—Cu1—Br196.27 (8)
 

Acknowledgements

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

References

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

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