Bromido(2-{1-[2-(morpholin-4-yl)ethyl-imino]-eth-yl}phenolato)copper(II).

In the title complex, [CuBr(C(14)H(19)N(2)O(2))], 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, with the N atoms in a cis arrangement. The morpholine ring adopts a chair conformation.

Related literature

For background to Schiff base complexes and a related structure, see: Zhao (2008 ▶). For similar copper(II) complexes with Schiff bases, see: Zhu et al. (2005 ▶); Ni et al. (2005 ▶); Zhu (2010 ▶); Suleiman Gwaram et al. (2010 ▶).

Experimental

Crystal data

[CuBr(C14H19N2O2)]

M = 390.76

Monoclinic,

a = 10.808 (2) Å

b = 17.152 (3) Å

c = 8.107 (2) Å

β = 90.059 (1)°

V = 1502.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.11 mm−1

T = 298 K

0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.353, T max = 0.372

9814 measured reflections

3211 independent reflections

2506 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.171

S = 1.13

3211 reflections

182 parameters

H-atom parameters constrained

Δρmax = 1.06 e Å−3

Δρmin = −1.06 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/S160053681002670X/hb5543sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002670X/hb5543Isup2.hkl

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

[CuBr(C14H19N2O2)]	F(000) = 788
Mr = 390.76	Dx = 1.727 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3491 reflections
a = 10.808 (2) Å	θ = 2.7–26.4°
b = 17.152 (3) Å	µ = 4.11 mm−1
c = 8.107 (2) Å	T = 298 K
β = 90.059 (1)°	Block, blue
V = 1502.9 (5) Å3	0.32 × 0.30 × 0.30 mm
Z = 4

Bruker SMART CCD diffractometer	3211 independent reflections
Radiation source: fine-focus sealed tube	2506 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.353, Tmax = 0.372	k = −21→21
9814 measured reflections	l = −10→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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0288P)2 + 17.4414P] where P = (Fo2 + 2Fc2)/3
3211 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 1.06 e Å−3
0 restraints	Δρmin = −1.06 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	0.98896 (9)	0.13655 (6)	0.00058 (11)	0.0314 (3)
Br1	1.13378 (9)	0.10662 (6)	−0.21461 (11)	0.0482 (3)
N1	0.8594 (6)	0.1190 (4)	0.1576 (8)	0.0364 (16)
N2	1.1147 (5)	0.1243 (4)	0.1957 (7)	0.0268 (13)
O1	0.8763 (6)	0.1804 (4)	−0.1494 (8)	0.0513 (17)
O2	1.3588 (5)	0.0900 (4)	0.3093 (9)	0.0535 (17)
C1	0.6903 (8)	0.1273 (5)	−0.0276 (12)	0.042 (2)
C2	0.7578 (8)	0.1655 (5)	−0.1526 (11)	0.0408 (19)
C3	0.6965 (9)	0.1916 (5)	−0.2956 (12)	0.045 (2)
H3	0.7402	0.2196	−0.3746	0.054*
C4	0.5723 (9)	0.1763 (6)	−0.3203 (13)	0.055 (3)
H4	0.5337	0.1924	−0.4171	0.066*
C5	0.5052 (10)	0.1369 (7)	−0.2008 (14)	0.062 (3)
H5	0.4218	0.1262	−0.2180	0.075*
C6	0.5630 (9)	0.1130 (6)	−0.0536 (14)	0.055 (3)
H6	0.5170	0.0877	0.0272	0.066*
C7	0.7411 (7)	0.1089 (5)	0.1327 (11)	0.0368 (18)
C8	0.6584 (9)	0.0816 (7)	0.2725 (13)	0.060 (3)
H8A	0.7001	0.0418	0.3345	0.090*
H8B	0.5829	0.0609	0.2279	0.090*
H8C	0.6398	0.1248	0.3436	0.090*
C9	0.9094 (8)	0.1095 (6)	0.3272 (11)	0.046 (2)
H9A	0.8534	0.1327	0.4068	0.055*
H9B	0.9184	0.0546	0.3532	0.055*
C10	1.0320 (8)	0.1490 (5)	0.3342 (10)	0.041 (2)
H10A	1.0717	0.1369	0.4385	0.050*
H10B	1.0199	0.2050	0.3292	0.050*
C11	1.2203 (9)	0.1793 (5)	0.1721 (12)	0.049 (2)
H11A	1.1904	0.2326	0.1744	0.058*
H11B	1.2586	0.1701	0.0657	0.058*
C12	1.3139 (9)	0.1672 (7)	0.3076 (14)	0.059 (3)
H12A	1.3826	0.2029	0.2920	0.070*
H12B	1.2760	0.1789	0.4132	0.070*
C13	1.2577 (9)	0.0373 (6)	0.3351 (11)	0.048 (2)
H13A	1.2214	0.0473	0.4423	0.057*
H13B	1.2888	−0.0158	0.3352	0.057*
C14	1.1597 (8)	0.0450 (5)	0.2050 (10)	0.0362 (18)
H14A	1.1934	0.0298	0.0990	0.043*
H14B	1.0914	0.0102	0.2304	0.043*

	U11	U22	U33	U12	U13	U23
Cu1	0.0325 (5)	0.0353 (5)	0.0264 (5)	−0.0002 (4)	−0.0019 (4)	0.0039 (4)
Br1	0.0548 (6)	0.0576 (6)	0.0322 (5)	−0.0018 (4)	0.0064 (4)	0.0000 (4)
N1	0.038 (4)	0.044 (4)	0.027 (3)	0.008 (3)	−0.006 (3)	0.008 (3)
N2	0.026 (3)	0.038 (4)	0.017 (3)	−0.008 (3)	0.006 (2)	−0.010 (2)
O1	0.039 (3)	0.060 (4)	0.055 (4)	−0.004 (3)	−0.009 (3)	0.030 (3)
O2	0.028 (3)	0.068 (5)	0.064 (4)	0.005 (3)	0.003 (3)	0.014 (4)
C1	0.039 (5)	0.029 (4)	0.058 (6)	−0.002 (3)	−0.001 (4)	0.009 (4)
C2	0.046 (5)	0.036 (5)	0.040 (5)	0.006 (4)	−0.005 (4)	−0.004 (4)
C3	0.049 (5)	0.038 (5)	0.048 (5)	0.006 (4)	−0.008 (4)	0.001 (4)
C4	0.046 (6)	0.058 (6)	0.061 (6)	0.013 (5)	−0.024 (5)	−0.003 (5)
C5	0.052 (6)	0.068 (7)	0.068 (7)	−0.002 (5)	−0.024 (5)	−0.012 (6)
C6	0.039 (5)	0.058 (6)	0.068 (7)	0.005 (4)	−0.012 (5)	−0.007 (5)
C7	0.029 (4)	0.035 (4)	0.046 (5)	0.006 (3)	0.006 (3)	−0.005 (4)
C8	0.036 (5)	0.091 (8)	0.054 (6)	0.013 (5)	0.003 (4)	0.018 (6)
C9	0.038 (5)	0.065 (6)	0.035 (5)	0.005 (4)	0.011 (4)	−0.001 (4)
C10	0.043 (5)	0.052 (5)	0.029 (4)	0.007 (4)	0.002 (3)	−0.006 (4)
C11	0.061 (6)	0.034 (5)	0.051 (6)	−0.004 (4)	−0.012 (5)	0.003 (4)
C12	0.041 (5)	0.069 (7)	0.066 (7)	−0.014 (5)	−0.011 (5)	−0.009 (6)
C13	0.053 (6)	0.049 (6)	0.041 (5)	0.014 (4)	−0.004 (4)	0.008 (4)
C14	0.045 (5)	0.030 (4)	0.035 (4)	0.002 (3)	0.003 (4)	−0.001 (3)

Cu1—O1	1.877 (6)	C5—H5	0.9300
Cu1—N1	1.917 (7)	C6—H6	0.9300
Cu1—N2	2.095 (6)	C7—C8	1.518 (12)
Cu1—Br1	2.4006 (14)	C8—H8A	0.9600
N1—C7	1.306 (11)	C8—H8B	0.9600
N1—C9	1.486 (11)	C8—H8C	0.9600
N2—C14	1.447 (10)	C9—C10	1.489 (13)
N2—C11	1.494 (11)	C9—H9A	0.9700
N2—C10	1.497 (9)	C9—H9B	0.9700
O1—C2	1.306 (11)	C10—H10A	0.9700
O2—C12	1.411 (13)	C10—H10B	0.9700
O2—C13	1.434 (12)	C11—C12	1.508 (13)
C1—C6	1.413 (12)	C11—H11A	0.9700
C1—C2	1.411 (12)	C11—H11B	0.9700
C1—C7	1.445 (12)	C12—H12A	0.9700
C2—C3	1.408 (12)	C12—H12B	0.9700
C3—C4	1.382 (13)	C13—C14	1.500 (12)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.387 (16)	C13—H13B	0.9700
C4—H4	0.9300	C14—H14A	0.9700
C5—C6	1.407 (14)	C14—H14B	0.9700
O1—Cu1—N1	91.1 (3)	H8A—C8—H8B	109.5
O1—Cu1—N2	161.7 (3)	C7—C8—H8C	109.5
N1—Cu1—N2	87.5 (2)	H8A—C8—H8C	109.5
O1—Cu1—Br1	92.2 (2)	H8B—C8—H8C	109.5
N1—Cu1—Br1	157.9 (2)	C10—C9—N1	108.0 (7)
N2—Cu1—Br1	95.99 (16)	C10—C9—H9A	110.1
C7—N1—C9	118.9 (7)	N1—C9—H9A	110.1
C7—N1—Cu1	129.3 (6)	C10—C9—H9B	110.1
C9—N1—Cu1	111.5 (5)	N1—C9—H9B	110.1
C14—N2—C11	110.1 (6)	H9A—C9—H9B	108.4
C14—N2—C10	115.3 (6)	C9—C10—N2	112.0 (7)
C11—N2—C10	112.0 (6)	C9—C10—H10A	109.2
C14—N2—Cu1	110.6 (5)	N2—C10—H10A	109.2
C11—N2—Cu1	109.6 (5)	C9—C10—H10B	109.2
C10—N2—Cu1	98.7 (5)	N2—C10—H10B	109.2
C2—O1—Cu1	124.8 (6)	H10A—C10—H10B	107.9
C12—O2—C13	109.3 (7)	N2—C11—C12	109.4 (7)
C6—C1—C2	118.5 (9)	N2—C11—H11A	109.8
C6—C1—C7	117.7 (8)	C12—C11—H11A	109.8
C2—C1—C7	123.4 (8)	N2—C11—H11B	109.8
O1—C2—C3	114.5 (8)	C12—C11—H11B	109.8
O1—C2—C1	125.8 (8)	H11A—C11—H11B	108.2
C3—C2—C1	119.7 (8)	O2—C12—C11	111.5 (8)
C4—C3—C2	121.0 (9)	O2—C12—H12A	109.3
C4—C3—H3	119.5	C11—C12—H12A	109.3
C2—C3—H3	119.5	O2—C12—H12B	109.3
C5—C4—C3	120.0 (9)	C11—C12—H12B	109.3
C5—C4—H4	120.0	H12A—C12—H12B	108.0
C3—C4—H4	120.0	O2—C13—C14	112.3 (7)
C4—C5—C6	120.2 (10)	O2—C13—H13A	109.1
C4—C5—H5	119.9	C14—C13—H13A	109.1
C6—C5—H5	119.9	O2—C13—H13B	109.1
C5—C6—C1	120.5 (10)	C14—C13—H13B	109.1
C5—C6—H6	119.7	H13A—C13—H13B	107.9
C1—C6—H6	119.7	N2—C14—C13	110.9 (7)
N1—C7—C1	118.8 (8)	N2—C14—H14A	109.5
N1—C7—C8	120.2 (8)	C13—C14—H14A	109.5
C1—C7—C8	121.0 (8)	N2—C14—H14B	109.5
C7—C8—H8A	109.5	C13—C14—H14B	109.5
C7—C8—H8B	109.5	H14A—C14—H14B	108.1

Cu1—O1	1.877 (6)
Cu1—N1	1.917 (7)
Cu1—N2	2.095 (6)
Cu1—Br1	2.4006 (14)

O1—Cu1—N1	91.1 (3)
O1—Cu1—N2	161.7 (3)
N1—Cu1—N2	87.5 (2)
O1—Cu1—Br1	92.2 (2)
N1—Cu1—Br1	157.9 (2)
N2—Cu1—Br1	95.99 (16)