Bis(2,1,3-benzoselenadiazole-κN)dibromidocopper(II)

Fun, H.-K.; Goh, J.H.; Maity, A.C.; Goswami, S.

doi:10.1107/S160053681005422X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m181-m182

doi:10.1107/S160053681005422X

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Bis(2,1,3-benzoselenadiazole-κN)dibromidocopper(II)

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § Annada C. Maity ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 20 December 2010; accepted 25 December 2010; online 15 January 2011)

In the title complex, [CuBr₂(C₆H₄N₂Se)₂], the Cu^II ion is tetracoordinated by two bromide anions and two N atoms in a distorted square-planar geometry. The two essentially planar 2,1,3-benzoselenadiazole ligands [maximum deviations = 0.012 (2) and 0.030 (2) Å] are approximately coplanar [dihedral angle = 6.14 (6)°]. In the crystal, short intermolecular Se⋯Br, Se⋯N and N⋯N interactions are observed. These short interactions and intermolecular C—H⋯Br hydrogen bonds link the complex molecules into two-dimensional arrays parallel to the ac plane.

Related literature

For general background to and applications of the title complex, see: Fun et al. (2008 ); Zhou et al. (2005 ). For related structures, see: Fun et al. (2008); Goswami et al. (2009 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

[CuBr₂(C₆H₄N₂Se)₂]
M_r = 589.50
Triclinic, $[P \overline 1]$
a = 8.3406 (1) Å
b = 9.5853 (1) Å
c = 10.2908 (1) Å
α = 94.627 (1)°
β = 109.640 (1)°
γ = 102.690 (1)°
V = 745.17 (1) Å³
Z = 2
Mo Kα radiation
μ = 11.71 mm⁻¹
T = 100 K
0.52 × 0.11 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.064, T_max = 0.550
47530 measured reflections
9041 independent reflections
6854 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.066
S = 1.02
9041 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −1.28 e Å⁻³

Table 1
Selected interatomic distances (Å)

Cu1—N3	2.0077 (15)
Cu1—N1	2.0106 (15)
Cu1—Br1	2.3987 (3)
Cu1—Br2	2.4449 (3)
Se1⋯N2	1.7768 (15)
Se1⋯N1	1.8131 (16)
Se2⋯N4	1.7854 (15)
Se2⋯N3	1.8097 (15)
Se1⋯Br1ⁱ	3.5223 (3)
Se2⋯N2ⁱⁱ	2.6848 (16)
N2⋯N4ⁱⁱⁱ	2.819 (2)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y, z-1; (iii) x, y, z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Br2^iv	0.93	2.74	3.464 (2)	135
C8—H8⋯Br1ⁱ	0.93	2.90	3.762 (2)	154
Symmetry codes: (i) -x+1, -y+2, -z+1; (iv) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005422X/sj5081sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681005422X/sj5081Isup2.hkl

checkCIF report

Comment top

The design and synthesis of metal-organic framework (MOF) materials are an interesting area nowadays. The coordination chemistry of 2,1,3-benzoselenadiazole (bsd) has been sparingly explored (Zhou et al., 2005). Recently we have shown that 2,1,3-bsd is capable of forming coordination networks with Zn(II) metal (Fun et al., 2008). In the present work, we report the coordination networks for Cu^II complex containing bsd. Reaction of 2,1,3-bsd with CuBr₂ results in the formation of the title copper complex.

The title complex comprises a neutral CuBr₂L₂ molecule (L = 2,1,3-bsd ligand). The Cu^II ion is tetra-coordinated by two Br^- ions and two L ligand-N atoms in a distorted square planar geometry, as indicated by angles of N1–Cu1–N3 = 172.82 (6)°, Br1–Cu1–Br2 = 170.661 (12)° and range of N–Cu–Br = 87.91 (5)–91.11 (5)°. The two ligands [(C1–C6/N1/N2/Se1) and (C6–C12/N3/N4/Se2)] are essentially planar, with maximum deviations of -0.012 (2) Å at atom C2 and 0.030 (2) Å at atom N3, respectively. These two ligands are approximately coplanar to one another, forming an interplanar angle of 6.14 (6)°. Selected bond lengths are listed in Table 1. All other bond lengths and angles are consistent to those observed in closely related structures (Fun et al., 2008; Goswami et al., 2009).

The interesting feature of the crystal packing is the observation of intermolecular short Se1···Br1, Se2···N2 and N2···N4 interactions (Table 1), as observed in the reported ZnCl₂L₂ structure (Fun et al., 2008). The title complex is interconnected into two-dimensional arrays lying parallel with the ac plane via these short interactions as well as intermolecular C2—H2···Br2 and C8—H8···Br1 hydrogen bonds (Table 2).

Related literature top

For general background to and applications of the title complex, see: Fun et al. (2008); Zhou et al. (2005). For related structures, see: Fun et al. (2008); Goswami et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2,1,3-bsd (1 g, 5.4 mol) and anhydrous copper bromide (606 mg, 2.72 mmol) in dry methanol (20 ml) was heated at 343–353 K for 2 h. After completion of the reaction, the mixture was allowed to cool to room temperature and the precipitate was collected by filtration. Recrystallization from methanol (25 %) in chloroform afforded brown microcrystalline solids of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2009).

Figures top

	Fig. 1. The molecular structure of the title complex, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. The crystal structure of the title complex, viewed along the b axis, showing a two-dimensional array parallel with the ac plane. Intermolecular interactions are shown as dashed lines.

Bis(2,1,3-benzoselenadiazole-κN)dibromidocopper(II) top

Crystal data top

[CuBr₂(C₆H₄N₂Se)₂]	Z = 2
M_r = 589.50	F(000) = 550
Triclinic, P1	D_x = 2.627 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3406 (1) Å	Cell parameters from 9451 reflections
b = 9.5853 (1) Å	θ = 2.1–39.8°
c = 10.2908 (1) Å	µ = 11.71 mm⁻¹
α = 94.627 (1)°	T = 100 K
β = 109.640 (1)°	Block, red
γ = 102.690 (1)°	0.52 × 0.11 × 0.06 mm
V = 745.17 (1) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9041 independent reflections
Radiation source: fine-focus sealed tube	6854 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 39.8°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.064, T_max = 0.550	k = −17→17
47530 measured reflections	l = −18→18

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.025P)² + 0.1897P] where P = (F_o² + 2F_c²)/3
9041 reflections	(Δ/σ)_max = 0.003
190 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −1.28 e Å⁻³

Crystal data top

[CuBr₂(C₆H₄N₂Se)₂]	γ = 102.690 (1)°
M_r = 589.50	V = 745.17 (1) Å³
Triclinic, P1	Z = 2
a = 8.3406 (1) Å	Mo Kα radiation
b = 9.5853 (1) Å	µ = 11.71 mm⁻¹
c = 10.2908 (1) Å	T = 100 K
α = 94.627 (1)°	0.52 × 0.11 × 0.06 mm
β = 109.640 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9041 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6854 reflections with I > 2σ(I)
T_min = 0.064, T_max = 0.550	R_int = 0.048
47530 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.02	Δρ_max = 0.96 e Å⁻³
9041 reflections	Δρ_min = −1.28 e Å⁻³
190 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cu1	0.76323 (3)	0.96053 (2)	0.46923 (2)	0.01342 (4)
Se1	0.76418 (3)	1.00702 (2)	0.790290 (19)	0.01462 (4)
Se2	0.76370 (3)	0.96029 (2)	0.148426 (18)	0.01419 (4)
Br1	0.50628 (3)	0.76430 (2)	0.346275 (19)	0.01659 (4)
Br2	0.99180 (3)	1.18054 (2)	0.602981 (19)	0.01630 (4)
N1	0.7843 (2)	0.89074 (17)	0.65184 (16)	0.0145 (3)
N2	0.7949 (2)	0.87760 (18)	0.90445 (16)	0.0157 (3)
N3	0.7309 (2)	1.05001 (17)	0.29546 (16)	0.0145 (3)
N4	0.7204 (2)	1.10188 (18)	0.05009 (16)	0.0156 (3)
C1	0.8108 (2)	0.7679 (2)	0.69755 (18)	0.0141 (3)
C2	0.8325 (3)	0.6474 (2)	0.6210 (2)	0.0168 (3)
H2	0.8267	0.6476	0.5292	0.020*
C3	0.8621 (3)	0.5318 (2)	0.6854 (2)	0.0188 (3)
H3	0.8784	0.4535	0.6365	0.023*
C4	0.8690 (3)	0.5269 (2)	0.8263 (2)	0.0188 (3)
H4	0.8888	0.4456	0.8660	0.023*
C5	0.8472 (3)	0.6385 (2)	0.9022 (2)	0.0180 (3)
H5	0.8509	0.6343	0.9931	0.022*
C6	0.8185 (2)	0.7628 (2)	0.83934 (19)	0.0149 (3)
C7	0.6893 (2)	1.1727 (2)	0.26414 (18)	0.0139 (3)
C8	0.6457 (3)	1.2712 (2)	0.34984 (19)	0.0168 (3)
H8	0.6437	1.2531	0.4368	0.020*
C9	0.6071 (3)	1.3927 (2)	0.3011 (2)	0.0188 (3)
H9	0.5777	1.4572	0.3560	0.023*
C10	0.6102 (3)	1.4242 (2)	0.1680 (2)	0.0199 (4)
H10	0.5866	1.5097	0.1401	0.024*
C11	0.6472 (3)	1.3311 (2)	0.0817 (2)	0.0181 (3)
H11	0.6471	1.3515	−0.0052	0.022*
C12	0.6860 (2)	1.2015 (2)	0.12748 (18)	0.0147 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01609 (10)	0.01305 (10)	0.01093 (9)	0.00325 (8)	0.00478 (7)	0.00314 (7)
Se1	0.01835 (8)	0.01413 (8)	0.01224 (7)	0.00580 (6)	0.00550 (6)	0.00300 (6)
Se2	0.01791 (8)	0.01411 (8)	0.01127 (7)	0.00550 (6)	0.00527 (6)	0.00277 (6)
Br1	0.01675 (8)	0.01600 (8)	0.01488 (7)	0.00238 (6)	0.00416 (6)	0.00318 (6)
Br2	0.01769 (8)	0.01514 (8)	0.01563 (8)	0.00415 (6)	0.00532 (6)	0.00391 (6)
N1	0.0175 (7)	0.0141 (7)	0.0120 (6)	0.0036 (5)	0.0058 (5)	0.0027 (5)
N2	0.0185 (7)	0.0179 (7)	0.0124 (6)	0.0071 (6)	0.0059 (5)	0.0043 (5)
N3	0.0179 (7)	0.0137 (7)	0.0120 (6)	0.0041 (5)	0.0057 (5)	0.0023 (5)
N4	0.0186 (7)	0.0175 (7)	0.0128 (6)	0.0071 (6)	0.0065 (5)	0.0050 (5)
C1	0.0147 (7)	0.0142 (7)	0.0134 (7)	0.0039 (6)	0.0048 (6)	0.0039 (6)
C2	0.0196 (8)	0.0158 (8)	0.0155 (7)	0.0042 (7)	0.0076 (7)	0.0016 (6)
C3	0.0209 (9)	0.0156 (8)	0.0191 (8)	0.0053 (7)	0.0062 (7)	0.0010 (6)
C4	0.0200 (9)	0.0163 (8)	0.0194 (8)	0.0059 (7)	0.0048 (7)	0.0067 (7)
C5	0.0220 (9)	0.0176 (8)	0.0157 (7)	0.0069 (7)	0.0065 (7)	0.0072 (6)
C6	0.0154 (7)	0.0158 (8)	0.0140 (7)	0.0044 (6)	0.0053 (6)	0.0036 (6)
C7	0.0145 (7)	0.0136 (7)	0.0130 (7)	0.0037 (6)	0.0041 (6)	0.0024 (6)
C8	0.0189 (8)	0.0191 (9)	0.0129 (7)	0.0064 (7)	0.0056 (6)	0.0017 (6)
C9	0.0198 (9)	0.0196 (9)	0.0175 (8)	0.0080 (7)	0.0061 (7)	0.0014 (7)
C10	0.0230 (9)	0.0178 (9)	0.0204 (8)	0.0086 (7)	0.0072 (7)	0.0060 (7)
C11	0.0221 (9)	0.0179 (8)	0.0160 (7)	0.0076 (7)	0.0069 (7)	0.0061 (6)
C12	0.0159 (7)	0.0153 (8)	0.0131 (7)	0.0042 (6)	0.0052 (6)	0.0034 (6)

Geometric parameters (Å, º) top

Cu1—N3	2.0077 (15)	C3—C4	1.437 (3)
Cu1—N1	2.0106 (15)	C3—H3	0.9300
Cu1—Br1	2.3987 (3)	C4—C5	1.354 (3)
Cu1—Br2	2.4449 (3)	C4—H4	0.9300
Se1—N2	1.7768 (15)	C5—C6	1.429 (3)
Se1—N1	1.8131 (16)	C5—H5	0.9300
Se2—N4	1.7854 (15)	C7—C8	1.426 (3)
Se2—N3	1.8097 (15)	C7—C12	1.448 (2)
N1—C1	1.339 (2)	C8—C9	1.365 (3)
N2—C6	1.328 (2)	C8—H8	0.9300
N3—C7	1.331 (2)	C9—C10	1.433 (3)
N4—C12	1.334 (2)	C9—H9	0.9300
C1—C2	1.424 (3)	C10—C11	1.363 (3)
C1—C6	1.444 (2)	C10—H10	0.9300
C2—C3	1.362 (3)	C11—C12	1.428 (3)
C2—H2	0.9300	C11—H11	0.9300

Cu1···N3	2.0077 (15)	Se2···N4	1.7854 (15)
Cu1···N1	2.0106 (15)	Se2···N3	1.8097 (15)
Cu1···Br1	2.3987 (3)	Se1···Br1ⁱ	3.5223 (3)
Cu1···Br2	2.4449 (3)	Se2···N2ⁱⁱ	2.6848 (16)
Se1···N2	1.7768 (15)	N2···N4ⁱⁱⁱ	2.819 (2)
Se1···N1	1.8131 (16)

N3—Cu1—N1	172.82 (6)	C5—C4—H4	119.4
N3—Cu1—Br1	90.80 (5)	C3—C4—H4	119.4
N1—Cu1—Br1	91.11 (5)	C4—C5—C6	118.41 (17)
N3—Cu1—Br2	89.08 (5)	C4—C5—H5	120.8
N1—Cu1—Br2	87.91 (5)	C6—C5—H5	120.8
Br1—Cu1—Br2	170.661 (12)	N2—C6—C5	123.19 (17)
N2—Se1—N1	92.13 (7)	N2—C6—C1	116.30 (16)
N4—Se2—N3	92.13 (7)	C5—C6—C1	120.50 (17)
C1—N1—Se1	108.34 (12)	N3—C7—C8	126.26 (16)
C1—N1—Cu1	132.71 (13)	N3—C7—C12	114.19 (16)
Se1—N1—Cu1	118.95 (8)	C8—C7—C12	119.53 (16)
C6—N2—Se1	108.82 (12)	C9—C8—C7	118.33 (17)
C7—N3—Se2	108.91 (12)	C9—C8—H8	120.8
C7—N3—Cu1	131.38 (13)	C7—C8—H8	120.8
Se2—N3—Cu1	119.70 (8)	C8—C9—C10	122.20 (18)
C12—N4—Se2	108.23 (12)	C8—C9—H9	118.9
N1—C1—C2	126.44 (16)	C10—C9—H9	118.9
N1—C1—C6	114.38 (16)	C11—C10—C9	121.24 (18)
C2—C1—C6	119.18 (16)	C11—C10—H10	119.4
C3—C2—C1	118.50 (17)	C9—C10—H10	119.4
C3—C2—H2	120.7	C10—C11—C12	118.52 (17)
C1—C2—H2	120.7	C10—C11—H11	120.7
C2—C3—C4	122.18 (18)	C12—C11—H11	120.7
C2—C3—H3	118.9	N4—C12—C11	123.37 (17)
C4—C3—H3	118.9	N4—C12—C7	116.52 (16)
C5—C4—C3	121.22 (18)	C11—C12—C7	120.11 (17)

N2—Se1—N1—C1	0.24 (14)	Se1—N2—C6—C1	−1.1 (2)
N2—Se1—N1—Cu1	179.82 (10)	C4—C5—C6—N2	179.72 (19)
Br1—Cu1—N1—C1	61.95 (18)	C4—C5—C6—C1	0.7 (3)
Br2—Cu1—N1—C1	−127.35 (18)	N1—C1—C6—N2	1.3 (3)
Br1—Cu1—N1—Se1	−117.52 (8)	C2—C1—C6—N2	−179.12 (17)
Br2—Cu1—N1—Se1	53.19 (8)	N1—C1—C6—C5	−179.62 (18)
N1—Se1—N2—C6	0.48 (14)	C2—C1—C6—C5	−0.1 (3)
N4—Se2—N3—C7	0.87 (14)	Se2—N3—C7—C8	177.08 (16)
N4—Se2—N3—Cu1	−178.25 (10)	Cu1—N3—C7—C8	−3.9 (3)
Br1—Cu1—N3—C7	112.79 (17)	Se2—N3—C7—C12	−1.4 (2)
Br2—Cu1—N3—C7	−57.87 (17)	Cu1—N3—C7—C12	177.57 (13)
Br1—Cu1—N3—Se2	−68.31 (9)	N3—C7—C8—C9	179.67 (19)
Br2—Cu1—N3—Se2	121.03 (9)	C12—C7—C8—C9	−1.9 (3)
N3—Se2—N4—C12	−0.07 (14)	C7—C8—C9—C10	−0.4 (3)
Se1—N1—C1—C2	179.64 (16)	C8—C9—C10—C11	2.0 (3)
Cu1—N1—C1—C2	0.1 (3)	C9—C10—C11—C12	−1.0 (3)
Se1—N1—C1—C6	−0.9 (2)	Se2—N4—C12—C11	179.34 (16)
Cu1—N1—C1—C6	179.63 (13)	Se2—N4—C12—C7	−0.7 (2)
N1—C1—C2—C3	178.66 (19)	C10—C11—C12—N4	178.62 (19)
C6—C1—C2—C3	−0.8 (3)	C10—C11—C12—C7	−1.3 (3)
C1—C2—C3—C4	1.1 (3)	N3—C7—C12—N4	1.5 (3)
C2—C3—C4—C5	−0.4 (3)	C8—C7—C12—N4	−177.12 (17)
C3—C4—C5—C6	−0.5 (3)	N3—C7—C12—C11	−178.57 (18)
Se1—N2—C6—C5	179.91 (16)	C8—C7—C12—C11	2.8 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Br2^iv	0.93	2.74	3.464 (2)	135
C8—H8···Br1ⁱ	0.93	2.90	3.762 (2)	154

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

Experimental details

Crystal data
Chemical formula	[CuBr₂(C₆H₄N₂Se)₂]
M_r	589.50
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.3406 (1), 9.5853 (1), 10.2908 (1)
α, β, γ (°)	94.627 (1), 109.640 (1), 102.690 (1)
V (Å³)	745.17 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	11.71
Crystal size (mm)	0.52 × 0.11 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.064, 0.550
No. of measured, independent and observed [I > 2σ(I)] reflections	47530, 9041, 6854
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.901

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.066, 1.02
No. of reflections	9041
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −1.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected interatomic distances (Å) top

Cu1···N3	2.0077 (15)	Se2···N4	1.7854 (15)
Cu1···N1	2.0106 (15)	Se2···N3	1.8097 (15)
Cu1···Br1	2.3987 (3)	Se1···Br1ⁱ	3.5223 (3)
Cu1···Br2	2.4449 (3)	Se2···N2ⁱⁱ	2.6848 (16)
Se1···N2	1.7768 (15)	N2···N4ⁱⁱⁱ	2.819 (2)
Se1···N1	1.8131 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Br2^iv	0.93	2.74	3.464 (2)	135
C8—H8···Br1ⁱ	0.93	2.90	3.762 (2)	154

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). ACM and SG thank the DST, Government of India [SR/S1/OC-13/2005] for financial support. ACM thanks the UGC, Goverment of India, for a fellowship.

References

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