Bis[4-(4-bromophenylimino-κN)pent-2-en-2-olato-κO]copper(II).

In the title compound, [Cu(C(11)H(11)BrNO)(2)], the Cu(II) atom is in a distorted square-planar geometry, with the two bidentate ketimine ligands positioned in a trans geometry. Two inter-molecular C-H⋯O hydrogen bond inter-actions are present which link the mol-ecules in a zigzag manner along the a axis. The mol-ecules pack in layers along the diagonal of the bc plane.

Related literature

For similar structures, see: Bourget-Merle et al. (2002 ▶); Bryndin et al. (2008 ▶) Hsu et al. (2004 ▶, 2007 ▶) John et al. (2007 ▶); Stender et al. (2001 ▶).

Experimental

Crystal data

[Cu(C11H11BrNO)2]

M = 569.77

Monoclinic,

a = 12.493 (3) Å

b = 11.559 (4) Å

c = 15.415 (4) Å

β = 92.306 (14)°

V = 2224.2 (11) Å3

Z = 4

Mo Kα radiation

μ = 4.60 mm−1

T = 100 K

0.64 × 0.25 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.262, T max = 0.502

13700 measured reflections

5558 independent reflections

4291 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.082

S = 1.00

5558 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.89 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042420/gg2104sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042420/gg2104Isup2.hkl

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

[Cu(C11H11BrNO)2]	F(000) = 1132
Mr = 569.77	Dx = 1.702 Mg m−3Dm = 1.702 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4022 reflections
a = 12.493 (3) Å	θ = 2.6–28.3°
b = 11.559 (4) Å	µ = 4.60 mm−1
c = 15.415 (4) Å	T = 100 K
β = 92.306 (14)°	Cuboid, black
V = 2224.2 (11) Å3	0.64 × 0.25 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	4291 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 28.4°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
Tmin = 0.262, Tmax = 0.502	k = −15→15
13700 measured reflections	l = −20→20
5558 independent reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0411P)2] where P = (Fo2 + 2Fc2)/3
5558 reflections	(Δ/σ)max = 0.001
266 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.89 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C11	0.8322 (2)	0.8020 (3)	0.36239 (16)	0.0212 (6)
H11A	0.9055	0.813	0.3859	0.032*
H11B	0.8011	0.8772	0.3462	0.032*
H11C	0.8331	0.7522	0.311	0.032*
C12	0.76552 (18)	0.7460 (2)	0.43032 (15)	0.0149 (5)
C13	0.66749 (18)	0.7913 (2)	0.44918 (15)	0.0175 (5)
H13	0.6461	0.8593	0.4185	0.021*
C14	0.59432 (18)	0.7476 (2)	0.50978 (16)	0.0167 (5)
C15	0.48851 (19)	0.8093 (3)	0.51301 (18)	0.0243 (6)
H15A	0.4366	0.7727	0.4723	0.036*
H15B	0.4978	0.8906	0.4969	0.036*
H15C	0.4622	0.8048	0.572	0.036*
C21	0.6951 (2)	0.2875 (3)	0.71567 (18)	0.0256 (6)
H21A	0.6228	0.3133	0.7287	0.038*
H21B	0.7318	0.259	0.7689	0.038*
H21C	0.6905	0.2252	0.6725	0.038*
C22	0.7570 (2)	0.3872 (2)	0.68015 (17)	0.0179 (5)
C23	0.8587 (2)	0.4111 (2)	0.71350 (17)	0.0202 (6)
H23	0.8847	0.3643	0.7604	0.024*
C24	0.92856 (19)	0.4990 (2)	0.68462 (16)	0.0177 (5)
C25	1.0380 (2)	0.5049 (3)	0.73005 (18)	0.0294 (7)
H25A	1.0898	0.463	0.6959	0.044*
H25B	1.0349	0.4697	0.7877	0.044*
H25C	1.0601	0.586	0.736	0.044*
C111	0.54017 (18)	0.6141 (2)	0.61825 (15)	0.0129 (5)
C112	0.56717 (19)	0.6087 (2)	0.70644 (16)	0.0174 (5)
H112	0.6316	0.6437	0.7283	0.021*
C113	0.50063 (19)	0.5526 (2)	0.76277 (16)	0.0177 (5)
H113	0.5191	0.5486	0.8231	0.021*
C114	0.40750 (18)	0.5026 (2)	0.73001 (15)	0.0150 (5)
C115	0.37692 (18)	0.5094 (2)	0.64311 (15)	0.0151 (5)
H115	0.3113	0.4764	0.622	0.018*
C116	0.44426 (18)	0.5657 (2)	0.58699 (15)	0.0149 (5)
H116	0.4246	0.571	0.5269	0.018*
C211	0.97726 (17)	0.6546 (2)	0.59351 (14)	0.0127 (5)
C212	0.95377 (18)	0.7715 (2)	0.59664 (15)	0.0150 (5)
H212	0.889	0.7959	0.6213	0.018*
C213	1.02240 (18)	0.8536 (2)	0.56474 (15)	0.0157 (5)
H213	1.0056	0.9337	0.5672	0.019*
C214	1.11628 (18)	0.8159 (2)	0.52909 (15)	0.0168 (5)
C215	1.14142 (19)	0.6996 (2)	0.52416 (16)	0.0187 (6)
H215	1.2062	0.6756	0.4994	0.022*
C216	1.07162 (18)	0.6190 (2)	0.55558 (16)	0.0159 (5)
H216	1.0877	0.5389	0.5515	0.019*
N1	0.61776 (14)	0.65887 (19)	0.56113 (12)	0.0133 (4)
N2	0.90082 (15)	0.57349 (18)	0.62280 (13)	0.0130 (4)
O1	0.80748 (12)	0.65429 (16)	0.46501 (10)	0.0152 (4)
O2	0.70804 (13)	0.44317 (15)	0.61821 (11)	0.0166 (4)
Cu1	0.75794 (2)	0.58295 (3)	0.567779 (18)	0.01230 (8)
Br1	0.32073 (2)	0.41819 (2)	0.806750 (16)	0.02103 (8)
Br2	1.21072 (2)	0.92786 (3)	0.48364 (2)	0.03221 (9)

	U11	U22	U33	U12	U13	U23
C11	0.0233 (13)	0.0226 (16)	0.0175 (12)	−0.0046 (11)	−0.0012 (10)	0.0066 (11)
C12	0.0180 (11)	0.0132 (13)	0.0130 (11)	−0.0037 (10)	−0.0052 (9)	0.0005 (10)
C13	0.0199 (12)	0.0158 (14)	0.0164 (12)	−0.0007 (10)	−0.0039 (10)	0.0069 (11)
C14	0.0161 (11)	0.0154 (14)	0.0183 (12)	−0.0011 (10)	−0.0050 (9)	−0.0016 (11)
C15	0.0200 (13)	0.0201 (16)	0.0324 (15)	0.0052 (11)	−0.0024 (11)	0.0068 (13)
C21	0.0281 (14)	0.0198 (16)	0.0287 (15)	−0.0056 (12)	−0.0016 (12)	0.0103 (13)
C22	0.0205 (12)	0.0140 (14)	0.0195 (13)	0.0000 (10)	0.0036 (10)	0.0017 (11)
C23	0.0240 (13)	0.0172 (14)	0.0190 (13)	0.0008 (11)	−0.0038 (10)	0.0098 (11)
C24	0.0189 (12)	0.0185 (15)	0.0156 (12)	0.0012 (11)	−0.0008 (9)	0.0026 (11)
C25	0.0215 (13)	0.037 (2)	0.0291 (15)	−0.0055 (13)	−0.0112 (11)	0.0184 (14)
C111	0.0132 (11)	0.0131 (13)	0.0123 (11)	0.0010 (9)	−0.0011 (9)	0.0007 (10)
C112	0.0162 (12)	0.0184 (14)	0.0171 (12)	−0.0017 (10)	−0.0040 (9)	−0.0022 (11)
C113	0.0192 (12)	0.0214 (15)	0.0121 (12)	−0.0018 (11)	−0.0024 (9)	−0.0025 (11)
C114	0.0136 (11)	0.0154 (14)	0.0164 (12)	0.0025 (10)	0.0047 (9)	−0.0021 (10)
C115	0.0120 (10)	0.0166 (14)	0.0166 (12)	−0.0004 (10)	−0.0010 (9)	−0.0038 (11)
C116	0.0142 (11)	0.0167 (14)	0.0136 (11)	0.0012 (10)	−0.0014 (9)	−0.0026 (10)
C211	0.0107 (10)	0.0167 (14)	0.0103 (11)	−0.0009 (10)	−0.0032 (8)	0.0000 (10)
C212	0.0139 (11)	0.0170 (14)	0.0140 (11)	0.0015 (10)	0.0010 (9)	−0.0030 (10)
C213	0.0176 (11)	0.0121 (13)	0.0172 (12)	0.0015 (10)	−0.0013 (9)	−0.0012 (10)
C214	0.0134 (11)	0.0190 (14)	0.0182 (12)	−0.0029 (10)	0.0011 (9)	0.0039 (11)
C215	0.0144 (11)	0.0210 (15)	0.0210 (13)	0.0015 (10)	0.0049 (10)	0.0030 (11)
C216	0.0167 (12)	0.0120 (13)	0.0188 (12)	0.0023 (10)	−0.0006 (10)	−0.0009 (10)
N1	0.0118 (9)	0.0144 (11)	0.0133 (10)	−0.0015 (8)	−0.0032 (7)	0.0014 (9)
N2	0.0117 (9)	0.0126 (11)	0.0147 (10)	−0.0002 (8)	−0.0004 (7)	0.0017 (9)
O1	0.0176 (8)	0.0154 (10)	0.0123 (8)	0.0008 (7)	−0.0018 (6)	0.0021 (7)
O2	0.0172 (8)	0.0118 (10)	0.0210 (9)	−0.0019 (7)	0.0013 (7)	0.0044 (7)
Cu1	0.01157 (14)	0.01196 (17)	0.01323 (15)	−0.00026 (11)	−0.00136 (11)	0.00234 (12)
Br1	0.02047 (14)	0.02328 (16)	0.01966 (14)	−0.00309 (11)	0.00480 (10)	0.00181 (11)
Br2	0.02029 (14)	0.02105 (17)	0.0562 (2)	−0.00094 (12)	0.01245 (13)	0.01269 (15)

C11—C12	1.509 (3)	C111—C116	1.391 (3)
C11—H11A	0.98	C111—N1	1.432 (3)
C11—H11B	0.98	C112—C113	1.387 (4)
C11—H11C	0.98	C112—H112	0.95
C12—O1	1.289 (3)	C113—C114	1.376 (3)
C12—C13	1.374 (3)	C113—H113	0.95
C13—C14	1.426 (3)	C114—C115	1.380 (3)
C13—H13	0.95	C114—Br1	1.905 (2)
C14—N1	1.321 (3)	C115—C116	1.392 (3)
C14—C15	1.505 (3)	C115—H115	0.95
C15—H15A	0.98	C116—H116	0.95
C15—H15B	0.98	C211—C212	1.385 (4)
C15—H15C	0.98	C211—C216	1.398 (3)
C21—C22	1.503 (4)	C211—N2	1.424 (3)
C21—H21A	0.98	C212—C213	1.382 (3)
C21—H21B	0.98	C212—H212	0.95
C21—H21C	0.98	C213—C214	1.385 (3)
C22—O2	1.287 (3)	C213—H213	0.95
C22—C23	1.380 (3)	C214—C215	1.383 (4)
C23—C24	1.422 (4)	C214—Br2	1.904 (3)
C23—H23	0.95	C215—C216	1.377 (4)
C24—N2	1.320 (3)	C215—H215	0.95
C24—C25	1.512 (3)	C216—H216	0.95
C25—H25A	0.98	N1—Cu1	1.958 (2)
C25—H25B	0.98	N2—Cu1	1.948 (2)
C25—H25C	0.98	O1—Cu1	1.9110 (17)
C111—C112	1.389 (3)	O2—Cu1	1.9085 (19)
C12—C11—H11A	109.5	C113—C112—H112	119.8
C12—C11—H11B	109.5	C111—C112—H112	119.8
H11A—C11—H11B	109.5	C114—C113—C112	119.1 (2)
C12—C11—H11C	109.5	C114—C113—H113	120.5
H11A—C11—H11C	109.5	C112—C113—H113	120.5
H11B—C11—H11C	109.5	C113—C114—C115	121.9 (2)
O1—C12—C13	125.2 (2)	C113—C114—Br1	118.74 (18)
O1—C12—C11	114.5 (2)	C115—C114—Br1	119.31 (18)
C13—C12—C11	120.3 (2)	C114—C115—C116	118.6 (2)
C12—C13—C14	127.2 (2)	C114—C115—H115	120.7
C12—C13—H13	116.4	C116—C115—H115	120.7
C14—C13—H13	116.4	C111—C116—C115	120.4 (2)
N1—C14—C13	122.4 (2)	C111—C116—H116	119.8
N1—C14—C15	121.5 (2)	C115—C116—H116	119.8
C13—C14—C15	116.2 (2)	C212—C211—C216	119.0 (2)
C14—C15—H15A	109.5	C212—C211—N2	119.1 (2)
C14—C15—H15B	109.5	C216—C211—N2	121.8 (2)
H15A—C15—H15B	109.5	C213—C212—C211	121.5 (2)
C14—C15—H15C	109.5	C213—C212—H212	119.3
H15A—C15—H15C	109.5	C211—C212—H212	119.3
H15B—C15—H15C	109.5	C212—C213—C214	118.2 (2)
C22—C21—H21A	109.5	C212—C213—H213	120.9
C22—C21—H21B	109.5	C214—C213—H213	120.9
H21A—C21—H21B	109.5	C215—C214—C213	121.7 (2)
C22—C21—H21C	109.5	C215—C214—Br2	119.67 (18)
H21A—C21—H21C	109.5	C213—C214—Br2	118.7 (2)
H21B—C21—H21C	109.5	C216—C215—C214	119.3 (2)
O2—C22—C23	125.3 (2)	C216—C215—H215	120.3
O2—C22—C21	114.8 (2)	C214—C215—H215	120.3
C23—C22—C21	119.8 (2)	C215—C216—C211	120.3 (3)
C22—C23—C24	126.5 (2)	C215—C216—H216	119.8
C22—C23—H23	116.8	C211—C216—H216	119.8
C24—C23—H23	116.8	C14—N1—C111	120.6 (2)
N2—C24—C23	123.0 (2)	C14—N1—Cu1	123.75 (16)
N2—C24—C25	120.7 (2)	C111—N1—Cu1	115.60 (16)
C23—C24—C25	116.2 (2)	C24—N2—C211	119.9 (2)
C24—C25—H25A	109.5	C24—N2—Cu1	124.07 (16)
C24—C25—H25B	109.5	C211—N2—Cu1	116.06 (15)
H25A—C25—H25B	109.5	C12—O1—Cu1	123.98 (15)
C24—C25—H25C	109.5	C22—O2—Cu1	125.06 (16)
H25A—C25—H25C	109.5	O2—Cu1—O1	145.59 (8)
H25B—C25—H25C	109.5	O2—Cu1—N2	94.80 (8)
C112—C111—C116	119.5 (2)	O1—Cu1—N2	93.64 (8)
C112—C111—N1	118.3 (2)	O2—Cu1—N1	95.43 (8)
C116—C111—N1	121.8 (2)	O1—Cu1—N1	94.70 (8)
C113—C112—C111	120.4 (2)	N2—Cu1—N1	148.20 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C115—H115···O1i	0.95	2.47	3.370 (3)	157
C215—H215···O2ii	0.95	2.54	3.378 (3)	147

Table 1

Selected bond lengths (Å)

N1—Cu1	1.958 (2)
N2—Cu1	1.948 (2)
O1—Cu1	1.9110 (17)
O2—Cu1	1.9085 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C115—H115⋯O1i	0.95	2.47	3.370 (3)	157
C215—H215⋯O2ii	0.95	2.54	3.378 (3)	147

Symmetry codes: (i) ; (ii) .