{4,4′-Dibromo-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato-κ4O,N,N′,O′}copper(II)

Kargar, H.; Fun, H.-K.; Kia, R.

doi:10.1107/S1600536808036635

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1541-m1542

doi:10.1107/S1600536808036635

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{4,4′-Dibromo-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N′,O′}copper(II)

Hadi Kargar,^a Hoong-Kun Fun ^b ^* and Reza Kia ^b

^aDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 20 October 2008; accepted 7 November 2008; online 13 November 2008)

In the title compound, [Cu(C₁₉H₁₈Br₂N₂O₂)], the Cu^II ion is in a tetrahedrally distorted planar geometry, involving two N and two O atoms from the tetradentate Schiff base ligand. Intermolecular C—H⋯O hydrogen bonds form an eight-membered R₂²(8) motif. The dihedral angle betwen two benzene rings is 36.34 (9)°. There are intermolecular Cu⋯Br [3.4566 (5) Å] and Cu⋯·N [3.569 (3) Å] contacts, which are significantly shorter than the sum of van der Waals radii of the relevant atoms. These interactions, along with the intermolecular C—H⋯π and π–π [centroid–centroid distances of 3.709 (1) and 3.968 (2) Å] interactions, link neighbouring molecules into a one-dimensional infinite chain along the c axis.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For values of van der Waals radii, see: Bondi (1964 ). For related structures, see: Arıcı et al. (2001 ); Elmali et al. (2000 ); Hodgson (1975 ); Granovski et al. (1993 ). For the application of transition-metal complexes with Schiff base ligands, see: Blower (1998 ); Shahrokhian et al. (2000 ).

Experimental

Crystal data

[Cu(C₁₉H₁₈Br₂N₂O₂)]
M_r = 529.71
Triclinic, $[P \overline 1]$
a = 9.1416 (3) Å
b = 9.6398 (3) Å
c = 11.5382 (3) Å
α = 75.210 (2)°
β = 78.913 (2)°
γ = 73.435 (2)°
V = 934.42 (5) Å³
Z = 2
Mo Kα radiation
μ = 5.46 mm⁻¹
T = 100.0 (1) K
0.41 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.195, T_max = 0.443
29164 measured reflections
5410 independent reflections
4345 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.093
S = 1.07
5410 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 1.27 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O2	1.9027 (19)
Cu1—O1	1.9146 (18)
Cu1—N1	1.948 (2)
Cu1—N2	1.955 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.93	2.44	3.342 (3)	163
C10—H10B⋯Cg1ⁱⁱ	0.97	2.50	3.324 (3)	142
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1. Cg1 is the centroid of the Cu1, N2, O2, C11, C12, C17 ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036635/hy2161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036635/hy2161Isup2.hkl

checkCIF report

Comment top

Schiff base complexes are some of the most important stereochemical models in transition metal coordination chemistry, with their ease of preparation and structural variations (Elmali et al., 2000; Granovski et al.,1993). Transition metal complexes of Schiff base ligands are always of interest since they exhibit a marked tendency to oligomerize, thus leading to novel structural types, and also display a wide variety of magnetic properties (Blower, 1998; Shahrokhian et al., 2000). Many of the reported structural investigations of these complexes are discussed in some details in a review (Hodgson, 1975). Tetradentate Schiff base metal complexes may form trans or cis planar or tetrahedral structures (Elmali et al., 2000).

In the title compound (Fig. 1), the Cu^II ion shows a planar geometry distorted towards tetrahedral, which is defined by two imine N atoms and two phenolate O atoms of the tetradentate Schiff base ligand (Table 1). Intermolecular C—H···O hydrogen bonds form an eight-membered ring R₂²(8) motif (Fig. 2) (Bernstein et al., 1995). The bond lengths are within the normal ranges (Allen et al., 1987) and are comparable with the related structure (Arici et al., 2001). The dihedral angle between two benzene rings is 36.34 (9)°. The chelate ring composed of Cu1, N1, C8, C9, C10 and N2 atoms has a distorted boat conformation with puckering paremeters of Q = 0.807 (3) Å, Θ = 91.1 (2)° and Φ = 264.58 (17)°. The interesting feature of the crystal structure is short intermolecular Cu1···Br1ⁱⁱⁱ [3.4566 (5) Å] and Cu1···N2ⁱⁱ [3.569 (3) Å] interactions [symmetry codes: (ii) 1 - x, -y, 1 - z; (iii) 1 - x, -y, 2 - z], which are significantly shorter than the sum of van der Waals radii of the relevant atoms [Cu: 2.32; Br: 1.85; N: 1.55 Å (Bondi, 1964; Spek, 2003)]. These interactions along with the intermolecular C—H···π (Table 2) and π–π interactions [centroid–centroid distances: Cg2···Cg3ⁱⁱⁱ = 3.709 (1) and Cg2···Cg2ⁱⁱⁱ = 3.968 (2) Å; Cg2 = centroid of the C1–C6 ring and Cg3 = centroid of the Cu1, N1, O1, C1, C6, C7 ring] link the neighbouring molecules into one-dimensional infinite chains along the c axis (Fig. 3).

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For values of van der Waals radii, see: Bondi (1964). For related structures, see: Arici et al. (2001); Elmali et al. (2000); Hodgson (1975); Granovski et al. (1993). For the application of transition-metal complexes with Schiff base ligands, see: Blower (1998); Shahrokhian et al. (2000). Cg1 is the centroid of the Cu1, N2, O2, C11, C12, C17 ring.

Experimental top

The title compound was prepared based on the reported method (Arici et al., 2001). Single crystals suitable for X-ray analysis were obtained from an ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis, showing the hydrogen-bond motif R₂²(8).
	Fig. 3. The crystal packing of the title compound, viewed down the b axis, showing one-dimensional infinite chains along the c axis. Intermolecular Cu···Br and Cu···N interactions are shown as dashed lines.

{4,4'-Dibromo-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethylidyne)]diphenolato- κ⁴O,N,N',O'}copper(II) top

Crystal data top

[Cu(C₁₉H₁₈Br₂N₂O₂)]	Z = 2
M_r = 529.71	F(000) = 522
Triclinic, P1	D_x = 1.883 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1416 (3) Å	Cell parameters from 9921 reflections
b = 9.6398 (3) Å	θ = 2.2–33.8°
c = 11.5382 (3) Å	µ = 5.46 mm⁻¹
α = 75.210 (2)°	T = 100 K
β = 78.913 (2)°	Block, red
γ = 73.435 (2)°	0.41 × 0.21 × 0.15 mm
V = 934.42 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5410 independent reflections
Radiation source: fine-focus sealed tube	4345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.195, T_max = 0.443	k = −13→13
29164 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0524P)² + 0.5947P] where P = (F_o² + 2F_c²)/3
5410 reflections	(Δ/σ)_max = 0.002
235 parameters	Δρ_max = 1.27 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Cu(C₁₉H₁₈Br₂N₂O₂)]	γ = 73.435 (2)°
M_r = 529.71	V = 934.42 (5) Å³
Triclinic, P1	Z = 2
a = 9.1416 (3) Å	Mo Kα radiation
b = 9.6398 (3) Å	µ = 5.46 mm⁻¹
c = 11.5382 (3) Å	T = 100 K
α = 75.210 (2)°	0.41 × 0.21 × 0.15 mm
β = 78.913 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5410 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4345 reflections with I > 2σ(I)
T_min = 0.195, T_max = 0.443	R_int = 0.037
29164 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.07	Δρ_max = 1.27 e Å⁻³
5410 reflections	Δρ_min = −0.61 e Å⁻³
235 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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

	x	y	z	U_iso*/U_eq
Cu1	0.60215 (4)	0.07295 (3)	0.63222 (3)	0.01866 (8)
Br1	0.15151 (3)	−0.15996 (3)	1.22034 (2)	0.02498 (8)
Br2	0.80441 (4)	0.43866 (3)	−0.00230 (2)	0.02942 (9)
O1	0.4262 (2)	0.1481 (2)	0.73927 (16)	0.0210 (4)
O2	0.5974 (2)	0.2636 (2)	0.53114 (17)	0.0226 (4)
N1	0.6688 (3)	−0.1090 (2)	0.7503 (2)	0.0195 (4)
N2	0.6996 (3)	−0.0301 (2)	0.5008 (2)	0.0193 (4)
C1	0.3696 (3)	0.0739 (3)	0.8409 (2)	0.0187 (5)
C2	0.2233 (3)	0.1404 (3)	0.8980 (2)	0.0216 (5)
H2A	0.1701	0.2336	0.8604	0.026*
C3	0.1577 (3)	0.0712 (3)	1.0073 (2)	0.0222 (5)
H3A	0.0617	0.1176	1.0423	0.027*
C4	0.2363 (3)	−0.0692 (3)	1.0654 (2)	0.0209 (5)
C5	0.3765 (3)	−0.1391 (3)	1.0130 (2)	0.0202 (5)
H5A	0.4274	−0.2325	1.0520	0.024*
C6	0.4441 (3)	−0.0708 (3)	0.9004 (2)	0.0182 (5)
C7	0.5935 (3)	−0.1509 (3)	0.8535 (2)	0.0195 (5)
H7A	0.6390	−0.2402	0.9019	0.023*
C8	0.8231 (3)	−0.1986 (3)	0.7167 (3)	0.0220 (5)
H8A	0.8583	−0.2707	0.7877	0.026*
H8B	0.8935	−0.1347	0.6889	0.026*
C9	0.8276 (3)	−0.2804 (3)	0.6167 (2)	0.0215 (5)
C10	0.7088 (3)	−0.1897 (3)	0.5308 (2)	0.0208 (5)
H10A	0.7350	−0.2262	0.4566	0.025*
H10B	0.6084	−0.2049	0.5677	0.025*
C11	0.7379 (3)	0.0315 (3)	0.3905 (2)	0.0191 (5)
H11A	0.7818	−0.0304	0.3364	0.023*
C12	0.7183 (3)	0.1880 (3)	0.3441 (2)	0.0184 (5)
C13	0.7662 (3)	0.2337 (3)	0.2195 (2)	0.0200 (5)
H13A	0.8138	0.1630	0.1734	0.024*
C14	0.7432 (3)	0.3807 (3)	0.1663 (2)	0.0206 (5)
C15	0.6701 (3)	0.4888 (3)	0.2346 (2)	0.0221 (5)
H15A	0.6534	0.5887	0.1975	0.026*
C16	0.6231 (3)	0.4473 (3)	0.3559 (2)	0.0221 (5)
H16A	0.5755	0.5202	0.3999	0.027*
C17	0.6454 (3)	0.2960 (3)	0.4160 (2)	0.0193 (5)
C18	0.7856 (3)	−0.4283 (3)	0.6727 (3)	0.0255 (6)
H18A	0.7886	−0.4782	0.6098	0.038*
H18B	0.6840	−0.4106	0.7165	0.038*
H18C	0.8580	−0.4889	0.7268	0.038*
C19	0.9898 (3)	−0.3061 (3)	0.5469 (3)	0.0267 (6)
H19A	0.9944	−0.3565	0.4841	0.040*
H19B	1.0627	−0.3653	0.6011	0.040*
H19C	1.0142	−0.2124	0.5118	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02588 (17)	0.01331 (15)	0.01503 (15)	−0.00383 (12)	−0.00011 (12)	−0.00300 (12)
Br1	0.03447 (15)	0.02289 (14)	0.01814 (13)	−0.01260 (11)	0.00257 (10)	−0.00364 (10)
Br2	0.04858 (18)	0.01898 (14)	0.01683 (13)	−0.00907 (12)	0.00283 (11)	−0.00148 (10)
O1	0.0275 (9)	0.0161 (9)	0.0166 (9)	−0.0040 (7)	0.0010 (7)	−0.0029 (7)
O2	0.0316 (10)	0.0154 (9)	0.0182 (9)	−0.0037 (8)	0.0001 (7)	−0.0036 (7)
N1	0.0240 (11)	0.0159 (10)	0.0180 (10)	−0.0030 (8)	−0.0029 (8)	−0.0047 (9)
N2	0.0282 (11)	0.0131 (10)	0.0166 (10)	−0.0057 (8)	−0.0023 (8)	−0.0032 (8)
C1	0.0268 (13)	0.0156 (11)	0.0162 (11)	−0.0069 (10)	−0.0036 (9)	−0.0055 (9)
C2	0.0268 (13)	0.0164 (12)	0.0211 (13)	−0.0055 (10)	−0.0031 (10)	−0.0031 (10)
C3	0.0245 (13)	0.0219 (13)	0.0217 (13)	−0.0070 (10)	−0.0001 (10)	−0.0080 (11)
C4	0.0287 (13)	0.0198 (12)	0.0161 (12)	−0.0103 (10)	−0.0011 (10)	−0.0037 (10)
C5	0.0286 (13)	0.0170 (12)	0.0160 (12)	−0.0079 (10)	−0.0029 (10)	−0.0027 (10)
C6	0.0251 (12)	0.0154 (11)	0.0155 (11)	−0.0062 (9)	−0.0023 (9)	−0.0045 (10)
C7	0.0258 (13)	0.0154 (11)	0.0171 (12)	−0.0039 (10)	−0.0046 (10)	−0.0028 (10)
C8	0.0236 (12)	0.0184 (12)	0.0230 (13)	−0.0033 (10)	−0.0027 (10)	−0.0048 (11)
C9	0.0262 (13)	0.0162 (12)	0.0213 (13)	−0.0040 (10)	−0.0029 (10)	−0.0042 (10)
C10	0.0302 (13)	0.0137 (11)	0.0185 (12)	−0.0066 (10)	−0.0011 (10)	−0.0036 (10)
C11	0.0256 (12)	0.0147 (11)	0.0170 (12)	−0.0049 (9)	−0.0026 (9)	−0.0037 (9)
C12	0.0227 (12)	0.0152 (11)	0.0175 (12)	−0.0057 (9)	−0.0010 (9)	−0.0040 (10)
C13	0.0246 (12)	0.0187 (12)	0.0173 (12)	−0.0057 (10)	−0.0012 (10)	−0.0056 (10)
C14	0.0272 (13)	0.0188 (12)	0.0158 (12)	−0.0082 (10)	−0.0014 (10)	−0.0021 (10)
C15	0.0303 (14)	0.0137 (11)	0.0212 (13)	−0.0059 (10)	−0.0039 (10)	−0.0011 (10)
C16	0.0289 (13)	0.0147 (12)	0.0217 (13)	−0.0043 (10)	0.0001 (10)	−0.0056 (10)
C17	0.0232 (12)	0.0162 (11)	0.0181 (12)	−0.0052 (9)	−0.0013 (9)	−0.0038 (10)
C18	0.0361 (15)	0.0163 (12)	0.0230 (13)	−0.0064 (11)	−0.0042 (11)	−0.0020 (11)
C19	0.0269 (14)	0.0234 (14)	0.0287 (15)	−0.0048 (11)	0.0008 (11)	−0.0083 (12)

Geometric parameters (Å, º) top

Cu1—O2	1.9027 (19)	C8—H8A	0.9700
Cu1—O1	1.9146 (18)	C8—H8B	0.9700
Cu1—N1	1.948 (2)	C9—C18	1.530 (4)
Cu1—N2	1.955 (2)	C9—C19	1.531 (4)
Br1—C4	1.902 (3)	C9—C10	1.535 (4)
Br2—C14	1.901 (3)	C10—H10A	0.9700
O1—C1	1.305 (3)	C10—H10B	0.9700
O2—C17	1.303 (3)	C11—C12	1.437 (4)
N1—C7	1.286 (3)	C11—H11A	0.9300
N1—C8	1.467 (3)	C12—C13	1.413 (4)
N2—C11	1.287 (3)	C12—C17	1.432 (3)
N2—C10	1.470 (3)	C13—C14	1.366 (4)
C1—C2	1.422 (4)	C13—H13A	0.9300
C1—C6	1.425 (4)	C14—C15	1.405 (4)
C2—C3	1.379 (4)	C15—C16	1.373 (4)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.402 (4)	C16—C17	1.420 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.371 (4)	C18—H18A	0.9600
C5—C6	1.411 (4)	C18—H18B	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—C7	1.442 (4)	C19—H19A	0.9600
C7—H7A	0.9300	C19—H19B	0.9600
C8—C9	1.544 (4)	C19—H19C	0.9600

O2—Cu1—O1	92.77 (8)	C19—C9—C10	110.3 (2)
O2—Cu1—N1	160.11 (9)	C18—C9—C8	110.1 (2)
O1—Cu1—N1	93.32 (9)	C19—C9—C8	108.4 (2)
O2—Cu1—N2	93.40 (8)	C10—C9—C8	110.7 (2)
O1—Cu1—N2	151.78 (9)	N2—C10—C9	113.6 (2)
N1—Cu1—N2	90.14 (9)	N2—C10—H10A	108.8
C1—O1—Cu1	126.57 (17)	C9—C10—H10A	108.8
C17—O2—Cu1	128.01 (16)	N2—C10—H10B	108.8
C7—N1—C8	119.4 (2)	C9—C10—H10B	108.8
C7—N1—Cu1	125.97 (19)	H10A—C10—H10B	107.7
C8—N1—Cu1	114.58 (17)	N2—C11—C12	125.4 (2)
C11—N2—C10	118.7 (2)	N2—C11—H11A	117.3
C11—N2—Cu1	125.90 (18)	C12—C11—H11A	117.3
C10—N2—Cu1	114.85 (16)	C13—C12—C17	120.1 (2)
O1—C1—C2	118.6 (2)	C13—C12—C11	116.7 (2)
O1—C1—C6	124.7 (2)	C17—C12—C11	123.1 (2)
C2—C1—C6	116.7 (2)	C14—C13—C12	120.7 (2)
C3—C2—C1	122.2 (3)	C14—C13—H13A	119.7
C3—C2—H2A	118.9	C12—C13—H13A	119.7
C1—C2—H2A	118.9	C13—C14—C15	120.3 (2)
C2—C3—C4	119.7 (2)	C13—C14—Br2	119.65 (19)
C2—C3—H3A	120.1	C15—C14—Br2	120.0 (2)
C4—C3—H3A	120.1	C16—C15—C14	120.2 (2)
C5—C4—C3	120.3 (2)	C16—C15—H15A	119.9
C5—C4—Br1	119.8 (2)	C14—C15—H15A	119.9
C3—C4—Br1	119.8 (2)	C15—C16—C17	121.8 (2)
C4—C5—C6	120.7 (3)	C15—C16—H16A	119.1
C4—C5—H5A	119.7	C17—C16—H16A	119.1
C6—C5—H5A	119.7	O2—C17—C16	118.9 (2)
C5—C6—C1	120.4 (2)	O2—C17—C12	124.1 (2)
C5—C6—C7	116.8 (2)	C16—C17—C12	117.0 (2)
C1—C6—C7	122.7 (2)	C9—C18—H18A	109.5
N1—C7—C6	125.3 (2)	C9—C18—H18B	109.5
N1—C7—H7A	117.3	H18A—C18—H18B	109.5
C6—C7—H7A	117.3	C9—C18—H18C	109.5
N1—C8—C9	112.7 (2)	H18A—C18—H18C	109.5
N1—C8—H8A	109.0	H18B—C18—H18C	109.5
C9—C8—H8A	109.0	C9—C19—H19A	109.5
N1—C8—H8B	109.0	C9—C19—H19B	109.5
C9—C8—H8B	109.0	H19A—C19—H19B	109.5
H8A—C8—H8B	107.8	C9—C19—H19C	109.5
C18—C9—C19	110.4 (2)	H19A—C19—H19C	109.5
C18—C9—C10	106.9 (2)	H19B—C19—H19C	109.5

O2—Cu1—O1—C1	−174.0 (2)	C8—N1—C7—C6	177.2 (2)
N1—Cu1—O1—C1	−12.9 (2)	Cu1—N1—C7—C6	0.6 (4)
N2—Cu1—O1—C1	83.6 (3)	C5—C6—C7—N1	176.6 (2)
O1—Cu1—O2—C17	−151.9 (2)	C1—C6—C7—N1	−6.7 (4)
N1—Cu1—O2—C17	100.4 (3)	C7—N1—C8—C9	108.8 (3)
N2—Cu1—O2—C17	0.6 (2)	Cu1—N1—C8—C9	−74.2 (2)
O2—Cu1—N1—C7	114.8 (3)	N1—C8—C9—C18	−86.0 (3)
O1—Cu1—N1—C7	7.2 (2)	N1—C8—C9—C19	153.1 (2)
N2—Cu1—N1—C7	−144.8 (2)	N1—C8—C9—C10	32.0 (3)
O2—Cu1—N1—C8	−61.9 (3)	C11—N2—C10—C9	115.7 (3)
O1—Cu1—N1—C8	−169.52 (17)	Cu1—N2—C10—C9	−72.2 (2)
N2—Cu1—N1—C8	38.50 (18)	C18—C9—C10—N2	160.8 (2)
O2—Cu1—N2—C11	0.1 (2)	C19—C9—C10—N2	−79.2 (3)
O1—Cu1—N2—C11	102.4 (3)	C8—C9—C10—N2	40.8 (3)
N1—Cu1—N2—C11	−160.3 (2)	C10—N2—C11—C12	172.3 (2)
O2—Cu1—N2—C10	−171.27 (18)	Cu1—N2—C11—C12	1.2 (4)
O1—Cu1—N2—C10	−69.0 (3)	N2—C11—C12—C13	−179.2 (3)
N1—Cu1—N2—C10	28.31 (19)	N2—C11—C12—C17	−3.2 (4)
Cu1—O1—C1—C2	−169.15 (18)	C17—C12—C13—C14	−0.2 (4)
Cu1—O1—C1—C6	11.1 (4)	C11—C12—C13—C14	175.9 (2)
O1—C1—C2—C3	−178.0 (2)	C12—C13—C14—C15	−0.6 (4)
C6—C1—C2—C3	1.9 (4)	C12—C13—C14—Br2	−178.50 (19)
C1—C2—C3—C4	0.1 (4)	C13—C14—C15—C16	0.9 (4)
C2—C3—C4—C5	−1.3 (4)	Br2—C14—C15—C16	178.8 (2)
C2—C3—C4—Br1	176.5 (2)	C14—C15—C16—C17	−0.4 (4)
C3—C4—C5—C6	0.4 (4)	Cu1—O2—C17—C16	176.52 (18)
Br1—C4—C5—C6	−177.39 (19)	Cu1—O2—C17—C12	−2.5 (4)
C4—C5—C6—C1	1.7 (4)	C15—C16—C17—O2	−179.5 (2)
C4—C5—C6—C7	178.5 (2)	C15—C16—C17—C12	−0.4 (4)
O1—C1—C6—C5	177.1 (2)	C13—C12—C17—O2	179.8 (2)
C2—C1—C6—C5	−2.7 (4)	C11—C12—C17—O2	3.9 (4)
O1—C1—C6—C7	0.5 (4)	C13—C12—C17—C16	0.7 (4)
C2—C1—C6—C7	−179.3 (2)	C11—C12—C17—C16	−175.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.44	3.342 (3)	163
C10—H10B···Cg1ⁱⁱ	0.97	2.50	3.324 (3)	142

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₉H₁₈Br₂N₂O₂)]
M_r	529.71
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.1416 (3), 9.6398 (3), 11.5382 (3)
α, β, γ (°)	75.210 (2), 78.913 (2), 73.435 (2)
V (Å³)	934.42 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	5.46
Crystal size (mm)	0.41 × 0.21 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.195, 0.443
No. of measured, independent and observed [I > 2σ(I)] reflections	29164, 5410, 4345
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.093, 1.07
No. of reflections	5410
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.27, −0.61

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected bond lengths (Å) top

Cu1—O2	1.9027 (19)	Cu1—N1	1.948 (2)
Cu1—O1	1.9146 (18)	Cu1—N2	1.955 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.93	2.44	3.342 (3)	163
C10—H10B···Cg1ⁱⁱ	0.97	2.50	3.324 (3)	142

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

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK thanks PNU for financial support.

References

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