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

In the title complex, [CuBr(C(15)H(21)N(2)O)], 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 CuBrN(2)O 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 = 388.79

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 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

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026711/hb5544Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuBr(C15H21N2O)]	F(000) = 788
Mr = 388.79	Dx = 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

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

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(Fo2) + (0.0318P)2 + 0.4765P] where P = (Fo2 + 2Fc2)/3
3357 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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	0.50444 (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*

	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)

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

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)