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

Bungu, P.S.E.; Schutte, M.; Steyl, G.

doi:10.1107/S1600536812042420

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1373

doi:10.1107/S1600536812042420

Open

access

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

Paul S. E. Bungu,^a ^* Marietjie Schutte ^a and G. Steyl ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Nelson Mandela Drive, Bloemfontein 9301, South Africa
^*Correspondence e-mail: bungueps@ufs.ac.za

(Received 28 September 2012; accepted 10 October 2012; online 20 October 2012)

In the title compound, [Cu(C₁₁H₁₁BrNO)₂], the Cu^II atom is in a distorted square-planar geometry, with the two bidentate ketimine ligands positioned in a trans geometry. Two intermolecular C—H⋯O hydrogen bond interactions are present which link the molecules in a zigzag manner along the a axis. The molecules 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_r = 569.77
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 1.00
5558 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.89 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042420/gg2104sup1.cif

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

checkCIF report

Comment top

Beta-diketimine ligands are a versatile class of molecules that display an impressive range of diverse applications in coordination chemistry (Bourget-Merle et al. 2002). The success of these ligands (Stender et al. 2001) is presumably due to the scope for suitable tuning of the steric and electronic properties and due to its easy synthetic accessibility to coordinate to early transition metals (Hsu et al. 2004). Here we report the crystal structure of the Cu(II) complex containing a ketiminate ligand, [OC(Me)CHC(Me)NH (Ar)] where Ar = 4-bromophenyl. Structural analysis shows that the title compound crystallized as black cuboidal crystals in the monoclinic space group, P2₁/c, with one molecule in the asymmetric unit and with approximately non-crystallographic C2 symmetry. The complex shows a four coordinate environment around the copper atom where two ketimine ligands act as bidentate N,O-chelators and lie in the trans conformation to create two six-membered chelate rings (Cu—O—C—C—C—N). Similar structures are reported in literature and the bond distances and angles of this structure compare well to those in literature (Bryndin et al. 2008, Hsu et al. 2007, John et al.2007).

In this structure, the dihedral angles of the two coordinate planes, O1—Cu1—N2 and O2—Cu1—N1, are 24.1 (2)° and 21.1 (2)° respectively. Also, the Cu—O and Cu—N bond distances are all marginally unequal, hence suggesting distorted square-planer geometry around the Cu(II) center. In Figure 1, the Cu1—O1 and Cu1—O2 bond lengths are 1.911 (2) Å and 1.909 (2) Å while the Cu1—N1 and Cu1—N2 bond lengths were 1.958 (2) Å and 1.948 (2) Å respectively. The presence of the 4-bromophenyl group has caused a slight decrease in the Cu—N bond distances when compared to the respective analogues of copper ketimine complexes by Bryndin et al. 2008 (Cu—N = 1.960 (2) Å and 1.965 (2) Å) and Hsu et al. 2007 (Cu—N = 1.974 (1) Å and 1.974 (1) Å). Owing to the presence of the distortion, the four N—Cu—O bond angles are marginally different from the ideal value of a square planer geometry of 90° and are reported as 94.70 (8)° (N1—Cu1—O1) and 94.80 (8)° (N2—Cu1—O2). The diagonal angles, N1—Cu1—N2 and O1—Cu1—O2, are reported as 148.20 (9)° and 145.59 (8)° which also differ substantially from the ideal angle of 180° and are comparable to results reported by Bryndin et al. 2008 and Hsu et al. 2007.These differences were made apparent when comparing the results to the structures by John et al. 2007, where phenoxy-ketimine ligands were used as bidentate ligands for both Cu(II) and Ni(II), in which almost a perfect square planar geometry was obeserved. The stabilization is dominated by two intermolecular C—H···O hydrogen bonds (C115—H115···O1) 2.47 Å and C215—H215···O1 = 2.54 Å) (Table 2). π–π stacking is observed between neighbouring molecules with a centroid-to-hydrogen bond distance of 3.7236 (9) Å. Five pi-interactions (centroid-to-hydrogen) are observed with a distance varying between 3.527 (1) Å and 3.746 (1) Å. The hydrogen and pi-interactions as well as the pi–pi stacking is illustrated in Figure 2. The molecules pack in alternating layers along the c axis possibly due to the hydrogen- and π interactions.

Related literature top

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 top

Copper nitrate Cu(NO₃)₂ (100 mg, 0.044 mmol) was dissolved in MeOH and refluxed with 2 equivalent of C₁₁H₁₁BrONH (237 mg, 0.94 mmol) for 2 h. The product was filtered at ambient temperature and dried in air. Black crystals were grown overnight from chloroform/ether (1:1, 10 ml) mixture. (yield: 169 mg, 0.29 mmol and 67%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); 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).

Figures top

	Fig. 1. Representation of the title compound, showing the numbering scheme and displacement ellipsoids (50% probability).
	Fig. 2. Observed hydrogen interactions (green dashed line), π-π stacking (yellow dashed lines) and π-interactions(red dashed lines) in the crystal structure (hydrogen atoms omitted for clarity).

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

Crystal data top

[Cu(C₁₁H₁₁BrNO)₂]	F(000) = 1132
M_r = 569.77	D_x = 1.702 Mg m⁻³ D_m = 1.702 Mg m⁻³ D_m 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

Data collection top

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

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0411P)²] where P = (F_o² + 2F_c²)/3
5558 reflections	(Δ/σ)_max = 0.001
266 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

[Cu(C₁₁H₁₁BrNO)₂]	V = 2224.2 (11) Å³
M_r = 569.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.493 (3) Å	µ = 4.60 mm⁻¹
b = 11.559 (4) Å	T = 100 K
c = 15.415 (4) Å	0.64 × 0.25 × 0.15 mm
β = 92.306 (14)°

Data collection top

Bruker APEXII CCD diffractometer	5558 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4291 reflections with I > 2σ(I)
T_min = 0.262, T_max = 0.502	R_int = 0.034
13700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.00	Δρ_max = 0.65 e Å⁻³
5558 reflections	Δρ_min = −0.89 e Å⁻³
266 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₁₁BrNO)₂]
M_r	569.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.493 (3), 11.559 (4), 15.415 (4)
β (°)	92.306 (14)
V (Å³)	2224.2 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.60
Crystal size (mm)	0.64 × 0.25 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.262, 0.502
No. of measured, independent and observed [I > 2σ(I)] reflections	13700, 5558, 4291
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 1.00
No. of reflections	5558
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.89

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C115—H115···O1ⁱ	0.95	2.47	3.370 (3)	157.1
C215—H215···O2ⁱⁱ	0.95	2.54	3.378 (3)	146.5

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Acknowledgements

We would like to thank the crystallographer, Ricky Kotze, for the data collection, and the University of the Free State, the Chemistry Department, the NRF, Sasol Ltd and Inkaba YeAfrica for funding.

References

Bourget-Merle, L., Lappert, M. F. & Severn, J. R. (2002). Chem. Rev. 102, 3031–3065. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Bryndin, V. E., Smolentsev, A. I., Stabnikov, P. A. & Igumenov, I. K. (2008). J. Struct. Chem. 49, 556–559. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hsu, S.-H., Chang, J.-C., Lai, C.-L., Hu, C.-H., Lee, H. M., Lee, G.-H., Peng, S.-M. & Huang, J.-H. (2004). Inorg. Chem. 43, 6786–6792. Web of Science CSD CrossRef PubMed CAS Google Scholar
Hsu, S.-H., Li, C.-Y., Chiu, Y.-W., Chiu, M.-C., Lien, Y.-L., Kuo, P.-C., Lee, H. M., Huang, J.-H. & Cheng, C.-P. (2007). J. Organomet. Chem. 692, 5421–5428. Web of Science CSD CrossRef CAS Google Scholar
John, A., Katiyar, V., Pang, K., Shaikh, M. M., Nanavati, H. & Ghosh, P. (2007). Polyhedron, 26, 4033–4044. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stender, M., Eichler, B. E., Hardman, N. J., Power, P. P., Prust, J., Noltemeyer, M. & Roesky, H. W. (2001). Inorg. Chem. 40, 2794–2799. Web of Science CSD CrossRef PubMed CAS Google Scholar