(2,2′-Biquinoline-κ2N,N′)dibromidopalladium(II)

Ha, K.

doi:10.1107/S1600536812015425

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m618

doi:10.1107/S1600536812015425

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(2,2′-Biquinoline-κ²N,N′)dibromidopalladium(II)

Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 4 April 2012; accepted 9 April 2012; online 18 April 2012)

The Pd^II ion in the title complex, [PdBr₂(C₁₈H₁₂N₂)], is four-coordinated in a distorted square-planar environment by the two N atoms from the chelating 2,2′-biquinoline (Biqu) ligand and two mutually cis Br⁻ anions. The Biqu ligand is not planar, the dihedral angle between the quinoline systems being 17.2 (2)°. In the crystal, the complex molecules are connected by C—H⋯Br hydrogen bonds, forming chains along the c axis. When viewed down the b axis, successive chains are stacked in opposite directions. Intramolecular C—H⋯Br hydrogen bonds are also observed.

Related literature

For the crystal structure of the related chlorido Pd^II complex [PdCl₂(Biqu)], see: Muranishi et al. (2005 ).

Experimental

Crystal data

[PdBr₂(C₁₈H₁₂N₂)]
M_r = 522.50
Triclinic, $[P \overline 1]$
a = 8.9390 (5) Å
b = 9.2187 (5) Å
c = 11.1486 (6) Å
α = 72.398 (1)°
β = 69.318 (1)°
γ = 87.258 (1)°
V = 817.47 (8) Å³
Z = 2
Mo Kα radiation
μ = 6.02 mm⁻¹
T = 200 K
0.17 × 0.12 × 0.11 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.813, T_max = 1.000
5100 measured reflections
3126 independent reflections
2612 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 1.12
3126 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Br1	0.95	2.73	3.252 (5)	116
C14—H14⋯Br1ⁱ	0.95	2.90	3.754 (5)	150
C17—H17⋯Br2	0.95	2.85	3.261 (5)	107
Symmetry code: (i) x, y, z-1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015425/rk2351sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015425/rk2351Isup2.hkl

checkCIF report

Comment top

The title complex, [PdBr₂(C₁₈H₁₂N₂)], crystallized in the triclinic space group P1, whereas the analogous chlorido Pd^II complex [PdCl₂(C₁₈H₁₂N₂)] crystallized in the monoclinic space group P2₁/c (Muranishi et al., 2005).

The central Pd^II ion is four-coordinated in a distorted square-planar environment by the two N atoms from the chelating 2,2'-biquinoline (Biqu) ligand and two mutually cis Br^- anions (Fig. 1). The main contribution to the distortion is the tight N1-Pd1-N2 chelate angle of 78.90 (15)°, which results in non-linear trans axes [angle Br1–Pd1-N2 = 169.85 (10)° and angle Br2–Pd1-N1 = 167.99 (11)°]. The pairs of Pd-N and Pd–Br bond lengths are nearly equivalent [Pd-N = 2.064 (4)Å and 2.073 (4)Å; Pd–Br = 2.4113 (6)Å and 2.4151 (6)Å]. In the crystal structure, the Biqu ligand is not planar. The dihedral angle between the least-squares planes of the quinoline rings is 17.2 (2)°. The quinoline rings are inclined considerably to the least-squares plane of the PdBr₂N₂ unit [maximum deviation = 0.162 (1)Å], making dihedral angles of 41.46 (8)° and 44.33 (8)°. In the crystal, the complex molecules are connected by intermolecular C–H···Br hydrogen bonds, forming chains along the c axis (Fig. 2 and Table 1). When viewed down the b axis, successive chains are stacked in opposite directions. Intramolecular C–H···Br hydrogen bonds are also observed (Table 1). In addition, intermolecular π···π interactions between the six-membered rings are present, the shortest ring centroid-centroid distance being 3.753 (3)Å between pyridine rings.

Related literature top

For the crystal structure of the related chlorido Pd^II complex [PdCl₂(Biqu)], see: Muranishi et al. (2005).

Experimental top

To a solution of K₂PdBr₄ (0.1507 g, 0.299 mmol) in MeOH (20 ml) was added 2,2'-biquinoline (0.0772 g, 0.301 mmol) and stirred for 3 h at room temperature. After addition of H₂O (30 ml) to the reaction mixture, the formed precipitate was separated by filtration and washed with H₂O and acetone, and dried at 323 K, to give a pale red powder (0.1305 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from an acetone solution.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A molecular structure of the title complex with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the unit-cell contents of the title complex. Intermolecular C–H···Br H-bond interactions are drawn with dashed lines.

(2,2'-Biquinoline-κ²N,N')dibromidopalladium(II) top

Crystal data top

[PdBr₂(C₁₈H₁₂N₂)]	Z = 2
M_r = 522.50	F(000) = 500
Triclinic, P1	D_x = 2.123 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9390 (5) Å	Cell parameters from 3201 reflections
b = 9.2187 (5) Å	θ = 2.6–26.0°
c = 11.1486 (6) Å	µ = 6.02 mm⁻¹
α = 72.398 (1)°	T = 200 K
β = 69.318 (1)°	Block, red
γ = 87.258 (1)°	0.17 × 0.12 × 0.11 mm
V = 817.47 (8) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	3126 independent reflections
Radiation source: fine-focus sealed tube	2612 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
T_min = 0.813, T_max = 1.000	k = −11→10
5100 measured reflections	l = −13→13

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0152P)² + 2.2618P] where P = (F_o² + 2F_c²)/3
3126 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[PdBr₂(C₁₈H₁₂N₂)]	γ = 87.258 (1)°
M_r = 522.50	V = 817.47 (8) Å³
Triclinic, P1	Z = 2
a = 8.9390 (5) Å	Mo Kα radiation
b = 9.2187 (5) Å	µ = 6.02 mm⁻¹
c = 11.1486 (6) Å	T = 200 K
α = 72.398 (1)°	0.17 × 0.12 × 0.11 mm
β = 69.318 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3126 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2612 reflections with I > 2σ(I)
T_min = 0.813, T_max = 1.000	R_int = 0.018
5100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.12	Δρ_max = 0.67 e Å⁻³
3126 reflections	Δρ_min = −0.65 e Å⁻³
208 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 > 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.

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

	x	y	z	U_iso*/U_eq
Pd1	0.18588 (4)	0.23543 (4)	0.12682 (3)	0.02511 (10)
Br1	0.27983 (6)	0.30923 (6)	0.27917 (5)	0.03917 (15)
Br2	0.46432 (6)	0.24992 (6)	−0.01469 (5)	0.03636 (14)
N1	−0.0535 (4)	0.2651 (4)	0.2177 (4)	0.0272 (8)
N2	0.0935 (4)	0.2114 (4)	−0.0130 (4)	0.0262 (8)
C1	−0.1396 (6)	0.2604 (5)	0.3488 (5)	0.0298 (11)
C2	−0.0886 (6)	0.1742 (6)	0.4531 (5)	0.0355 (11)
H2	0.0083	0.1239	0.4333	0.043*
C3	−0.1800 (7)	0.1634 (6)	0.5841 (5)	0.0429 (13)
H3	−0.1471	0.1023	0.6546	0.051*
C4	−0.3222 (7)	0.2412 (7)	0.6164 (6)	0.0492 (15)
H4	−0.3821	0.2355	0.7073	0.059*
C5	−0.3710 (7)	0.3236 (7)	0.5160 (6)	0.0488 (15)
H5	−0.4661	0.3762	0.5375	0.059*
C6	−0.2853 (6)	0.3342 (6)	0.3796 (5)	0.0340 (11)
C7	−0.3393 (6)	0.4086 (6)	0.2740 (6)	0.0428 (13)
H7	−0.4315	0.4659	0.2909	0.051*
C8	−0.2613 (6)	0.3996 (5)	0.1484 (6)	0.0350 (12)
H8	−0.3032	0.4427	0.0789	0.042*
C9	−0.1173 (6)	0.3254 (5)	0.1219 (5)	0.0297 (11)
C10	−0.0315 (5)	0.2984 (5)	−0.0078 (5)	0.0267 (10)
C11	−0.0841 (6)	0.3520 (5)	−0.1181 (5)	0.0358 (12)
H11	−0.1739	0.4125	−0.1125	0.043*
C12	−0.0034 (6)	0.3152 (6)	−0.2328 (5)	0.0386 (13)
H12	−0.0303	0.3588	−0.3108	0.046*
C13	0.1192 (6)	0.2134 (6)	−0.2371 (5)	0.0367 (12)
C14	0.1985 (7)	0.1614 (7)	−0.3494 (5)	0.0426 (14)
H14	0.1746	0.2013	−0.4292	0.051*
C15	0.3082 (7)	0.0553 (6)	−0.3442 (6)	0.0432 (13)
H15	0.3597	0.0206	−0.4200	0.052*
C16	0.3463 (6)	−0.0038 (6)	−0.2269 (5)	0.0390 (12)
H16	0.4214	−0.0800	−0.2235	0.047*
C17	0.2771 (6)	0.0469 (5)	−0.1187 (5)	0.0327 (11)
H17	0.3049	0.0066	−0.0408	0.039*
C18	0.1640 (6)	0.1591 (5)	−0.1213 (5)	0.0293 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02232 (19)	0.03082 (19)	0.02356 (19)	0.00450 (14)	−0.01142 (15)	−0.00677 (15)
Br1	0.0325 (3)	0.0603 (3)	0.0312 (3)	0.0010 (2)	−0.0168 (2)	−0.0163 (3)
Br2	0.0241 (3)	0.0522 (3)	0.0343 (3)	0.0056 (2)	−0.0098 (2)	−0.0166 (2)
N1	0.021 (2)	0.030 (2)	0.031 (2)	0.0009 (16)	−0.0103 (17)	−0.0085 (17)
N2	0.023 (2)	0.031 (2)	0.023 (2)	0.0006 (16)	−0.0107 (16)	−0.0026 (17)
C1	0.024 (2)	0.031 (2)	0.037 (3)	−0.003 (2)	−0.011 (2)	−0.012 (2)
C2	0.034 (3)	0.040 (3)	0.031 (3)	−0.001 (2)	−0.011 (2)	−0.008 (2)
C3	0.041 (3)	0.049 (3)	0.032 (3)	−0.009 (3)	−0.007 (2)	−0.008 (3)
C4	0.042 (3)	0.061 (4)	0.035 (3)	−0.009 (3)	0.006 (3)	−0.021 (3)
C5	0.028 (3)	0.053 (3)	0.062 (4)	−0.002 (3)	0.000 (3)	−0.032 (3)
C6	0.021 (2)	0.035 (3)	0.043 (3)	−0.002 (2)	−0.006 (2)	−0.015 (2)
C7	0.029 (3)	0.038 (3)	0.067 (4)	0.010 (2)	−0.017 (3)	−0.026 (3)
C8	0.028 (3)	0.032 (3)	0.050 (3)	0.004 (2)	−0.021 (2)	−0.012 (2)
C9	0.028 (3)	0.026 (2)	0.041 (3)	0.002 (2)	−0.020 (2)	−0.010 (2)
C10	0.026 (2)	0.023 (2)	0.033 (3)	−0.0025 (19)	−0.015 (2)	−0.005 (2)
C11	0.033 (3)	0.034 (3)	0.048 (3)	0.001 (2)	−0.027 (3)	−0.008 (2)
C12	0.046 (3)	0.042 (3)	0.032 (3)	−0.008 (3)	−0.026 (3)	−0.001 (2)
C13	0.037 (3)	0.043 (3)	0.030 (3)	−0.006 (2)	−0.015 (2)	−0.007 (2)
C14	0.046 (3)	0.058 (4)	0.023 (3)	−0.018 (3)	−0.013 (2)	−0.007 (2)
C15	0.040 (3)	0.053 (3)	0.037 (3)	−0.007 (3)	−0.004 (3)	−0.025 (3)
C16	0.035 (3)	0.038 (3)	0.045 (3)	−0.005 (2)	−0.009 (2)	−0.018 (3)
C17	0.033 (3)	0.035 (3)	0.030 (3)	0.000 (2)	−0.010 (2)	−0.011 (2)
C18	0.031 (3)	0.033 (3)	0.027 (3)	−0.005 (2)	−0.013 (2)	−0.009 (2)

Geometric parameters (Å, º) top

Pd1—N1	2.064 (4)	C7—H7	0.9500
Pd1—N2	2.073 (4)	C8—C9	1.407 (7)
Pd1—Br1	2.4113 (6)	C8—H8	0.9500
Pd1—Br2	2.4151 (6)	C9—C10	1.468 (7)
N1—C9	1.349 (6)	C10—C11	1.413 (6)
N1—C1	1.378 (6)	C11—C12	1.363 (7)
N2—C10	1.339 (6)	C11—H11	0.9500
N2—C18	1.369 (6)	C12—C13	1.405 (7)
C1—C2	1.405 (7)	C12—H12	0.9500
C1—C6	1.421 (7)	C13—C14	1.415 (7)
C2—C3	1.373 (7)	C13—C18	1.425 (6)
C2—H2	0.9500	C14—C15	1.355 (8)
C3—C4	1.416 (8)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.411 (8)
C4—C5	1.350 (8)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.357 (7)
C5—C6	1.415 (7)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.413 (7)
C6—C7	1.404 (7)	C17—H17	0.9500
C7—C8	1.352 (7)

N1—Pd1—N2	78.90 (15)	C7—C8—C9	119.2 (5)
N1—Pd1—Br1	96.71 (11)	C7—C8—H8	120.4
N2—Pd1—Br1	169.85 (10)	C9—C8—H8	120.4
N1—Pd1—Br2	167.99 (11)	N1—C9—C8	121.8 (5)
N2—Pd1—Br2	96.02 (11)	N1—C9—C10	114.9 (4)
Br1—Pd1—Br2	86.49 (2)	C8—C9—C10	123.1 (4)
C9—N1—C1	119.3 (4)	N2—C10—C11	121.6 (4)
C9—N1—Pd1	109.1 (3)	N2—C10—C9	116.2 (4)
C1—N1—Pd1	130.2 (3)	C11—C10—C9	122.1 (4)
C10—N2—C18	120.3 (4)	C12—C11—C10	118.7 (5)
C10—N2—Pd1	107.9 (3)	C12—C11—H11	120.7
C18—N2—Pd1	129.2 (3)	C10—C11—H11	120.7
N1—C1—C2	119.9 (4)	C11—C12—C13	120.8 (5)
N1—C1—C6	120.1 (4)	C11—C12—H12	119.6
C2—C1—C6	119.9 (5)	C13—C12—H12	119.6
C3—C2—C1	119.4 (5)	C12—C13—C14	123.4 (5)
C3—C2—H2	120.3	C12—C13—C18	117.9 (5)
C1—C2—H2	120.3	C14—C13—C18	118.7 (5)
C2—C3—C4	121.6 (5)	C15—C14—C13	120.7 (5)
C2—C3—H3	119.2	C15—C14—H14	119.6
C4—C3—H3	119.2	C13—C14—H14	119.6
C5—C4—C3	118.8 (5)	C14—C15—C16	120.3 (5)
C5—C4—H4	120.6	C14—C15—H15	119.9
C3—C4—H4	120.6	C16—C15—H15	119.9
C4—C5—C6	122.2 (5)	C17—C16—C15	120.9 (5)
C4—C5—H5	118.9	C17—C16—H16	119.6
C6—C5—H5	118.9	C15—C16—H16	119.6
C7—C6—C5	123.6 (5)	C16—C17—C18	120.4 (5)
C7—C6—C1	118.3 (5)	C16—C17—H17	119.8
C5—C6—C1	118.0 (5)	C18—C17—H17	119.8
C8—C7—C6	120.6 (5)	N2—C18—C17	121.0 (4)
C8—C7—H7	119.7	N2—C18—C13	120.1 (4)
C6—C7—H7	119.7	C17—C18—C13	118.9 (4)

N2—Pd1—N1—C9	−29.4 (3)	C1—N1—C9—C10	−168.6 (4)
Br1—Pd1—N1—C9	141.3 (3)	Pd1—N1—C9—C10	23.2 (5)
Br2—Pd1—N1—C9	36.4 (7)	C7—C8—C9—N1	−1.0 (7)
N2—Pd1—N1—C1	164.1 (4)	C7—C8—C9—C10	174.6 (5)
Br1—Pd1—N1—C1	−25.1 (4)	C18—N2—C10—C11	−6.7 (7)
Br2—Pd1—N1—C1	−130.0 (5)	Pd1—N2—C10—C11	156.5 (4)
N1—Pd1—N2—C10	30.8 (3)	C18—N2—C10—C9	169.1 (4)
Br1—Pd1—N2—C10	−34.3 (8)	Pd1—N2—C10—C9	−27.7 (4)
Br2—Pd1—N2—C10	−138.2 (3)	N1—C9—C10—N2	3.3 (6)
N1—Pd1—N2—C18	−168.0 (4)	C8—C9—C10—N2	−172.6 (4)
Br1—Pd1—N2—C18	126.9 (5)	N1—C9—C10—C11	179.1 (4)
Br2—Pd1—N2—C18	23.0 (4)	C8—C9—C10—C11	3.1 (7)
C9—N1—C1—C2	168.6 (4)	N2—C10—C11—C12	−0.9 (7)
Pd1—N1—C1—C2	−26.1 (6)	C9—C10—C11—C12	−176.4 (4)
C9—N1—C1—C6	−7.3 (6)	C10—C11—C12—C13	6.4 (7)
Pd1—N1—C1—C6	158.0 (3)	C11—C12—C13—C14	174.8 (5)
N1—C1—C2—C3	−176.4 (4)	C11—C12—C13—C18	−4.5 (7)
C6—C1—C2—C3	−0.5 (7)	C12—C13—C14—C15	−175.5 (5)
C1—C2—C3—C4	−2.1 (8)	C18—C13—C14—C15	3.8 (8)
C2—C3—C4—C5	2.2 (8)	C13—C14—C15—C16	−0.7 (8)
C3—C4—C5—C6	0.3 (9)	C14—C15—C16—C17	−1.6 (8)
C4—C5—C6—C7	174.7 (5)	C15—C16—C17—C18	0.6 (7)
C4—C5—C6—C1	−2.8 (8)	C10—N2—C18—C17	−169.1 (4)
N1—C1—C6—C7	1.1 (7)	Pd1—N2—C18—C17	31.7 (6)
C2—C1—C6—C7	−174.7 (4)	C10—N2—C18—C13	8.5 (6)
N1—C1—C6—C5	178.7 (4)	Pd1—N2—C18—C13	−150.7 (4)
C2—C1—C6—C5	2.9 (7)	C16—C17—C18—N2	−179.9 (4)
C5—C6—C7—C8	−172.2 (5)	C16—C17—C18—C13	2.5 (7)
C1—C6—C7—C8	5.3 (7)	C12—C13—C18—N2	−3.0 (7)
C6—C7—C8—C9	−5.3 (8)	C14—C13—C18—N2	177.7 (4)
C1—N1—C9—C8	7.4 (7)	C12—C13—C18—C17	174.7 (4)
Pd1—N1—C9—C8	−160.8 (4)	C14—C13—C18—C17	−4.7 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Br1	0.95	2.73	3.252 (5)	116
C14—H14···Br1ⁱ	0.95	2.90	3.754 (5)	150
C17—H17···Br2	0.95	2.85	3.261 (5)	107

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	[PdBr₂(C₁₈H₁₂N₂)]
M_r	522.50
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	8.9390 (5), 9.2187 (5), 11.1486 (6)
α, β, γ (°)	72.398 (1), 69.318 (1), 87.258 (1)
V (Å³)	817.47 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.02
Crystal size (mm)	0.17 × 0.12 × 0.11

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.813, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5100, 3126, 2612
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.070, 1.12
No. of reflections	3126
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.65

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Br1	0.95	2.73	3.252 (5)	115.5
C14—H14···Br1ⁱ	0.95	2.90	3.754 (5)	149.9
C17—H17···Br2	0.95	2.85	3.261 (5)	107.1

Symmetry code: (i) x, y, z−1.

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011-0030747).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Muranishi, Y., Wang, Y., Odoko, M. & Okabe, N. (2005). Acta Cryst. C61, m307–m310. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar