trans-Dibromidobis[diphen­yl(p-tol­yl)phosphine]palladium(II)

Kirsten, L.; Steyl, G.; Roodt, A.

doi:10.1107/S1600536809045401

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1564

doi:10.1107/S1600536809045401

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trans-Dibromidobis[diphenyl(p-tolyl)phosphine]palladium(II)

Leo Kirsten,^a ^* Gideon Steyl ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: leokirsten@gmail.com

(Received 22 October 2009; accepted 29 October 2009; online 14 November 2009)

In the title compound, [PdBr₂(C₁₉H₁₇P)₂], the Pd^II ion resides on a centre of symmetry and is coordinated by two Br anions [Pd—Br = 2.4266 (2) Å] and two P-donor ligands [Pd—P = 2.3462 (5) Å] in a slightly distorted square-planar geometry [P—Pd—Br = 93.528 (12)°]. Weak intermolecular C—H⋯Br hydrogen bonds link molecules into chains extended in [1 $[\overline{1}]$ 0].

Related literature

For the isostructural compound, trans-[PdCl₂{P((Ph)₂(p-Tol))}₂], in which the Pd centers are coordinated by Cl anions instead of Br, see: Steyl et al. (2006 ).

Experimental

Crystal data

[PdBr₂(C₁₉H₁₇P)₂]
M_r = 818.81
Triclinic, $[P \overline 1]$
a = 10.0321 (4) Å
b = 10.0521 (4) Å
c = 10.2967 (4) Å
α = 70.876 (2)°
β = 68.288 (2)°
γ = 60.312 (2)°
V = 824.54 (6) Å³
Z = 1
Mo Kα radiation
μ = 3.11 mm⁻¹
T = 100 K
0.33 × 0.11 × 0.09 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.427, T_max = 0.767
25915 measured reflections
3982 independent reflections
3621 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.051
S = 1.04
3982 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯Brⁱ	0.93	2.88	3.7498 (19)	157
C22—H22⋯Brⁱⁱ	0.93	2.71	3.501 (2)	144
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004 ); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045401/cv2640sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045401/cv2640Isup2.hkl

checkCIF report

Comment top

This study is aimed at expanding the knowledge of trans square-planar palladium complexes containing phosphine donor ligands and bromido or chlorido anions as coordinating atoms.

The title compound is centrosymmetric with a slightly distorted-square-planar geometry, as seen by the cis angle P—Pd—Br of 93.528 (12)°. The packing of the title compound is stabilized by two weak intermolecular C—H···Br hydrogen bonds (Table 1).

The corresponding chloro complex (Steyl et al., 2006) is iso-structural to the title complex when comparing the geometrical parameters as well as the crystallization mode. The RMS error of 0.061 Å also indicate the iso-structurality of the two complexes (the title complex superimposed with the corresponding dichloro-palladium complex (Steyl et al., 2006) including the Pd, Cl(Br), P and first C atoms of the phenyl rings).

Related literature top

For the isostructural compound, trans-[PdCl₂{P((Ph)₂(p-Tol))}₂], in which the Pd centers are coordinated by Cl anions instead of Br, see Steyl et al. (2006).

Experimental top

The title complex was synthesized by the addition of 2.2 equivalents of diphenyl(p-tolyl)phosphine (16 mg, 0.059 mmol) to [Pd(COD)Br₂] (10 mg, 0.026 mmol) in 10 ml of dichloromethane while stirring for 5 minutes. Slow evaporation of the solvent resulted in orange crystals suitable for X-Ray diffraction (yield 71%, 16 mg).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A sketch of the title compound showing the atomic numbering and 50% probability displacement ellipsoids [symmetry code: (i) 1 - x,1 - y,1 - z]. For the phenyl rings the first digit refers to ring number and the second digit to the atom in the ring. Hydrogen atoms have been omitted for clarity.

trans-Dibromidobis[diphenyl(p-tolyl)phosphine]palladium(II) top

Crystal data top

[PdBr₂(C₁₉H₁₇P)₂]	Z = 1
M_r = 818.81	F(000) = 408
Triclinic, P1	D_x = 1.649 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0321 (4) Å	Cell parameters from 6740 reflections
b = 10.0521 (4) Å	θ = 2.4–28.3°
c = 10.2967 (4) Å	µ = 3.11 mm⁻¹
α = 70.876 (2)°	T = 100 K
β = 68.288 (2)°	Cuboid, orange
γ = 60.312 (2)°	0.33 × 0.11 × 0.09 mm
V = 824.54 (6) Å³

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	3982 independent reflections
Radiation source: fine-focus sealed tube	3621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 512 pixels mm^-1	θ_max = 28.0°, θ_min = 2.4°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −13→13
T_min = 0.427, T_max = 0.767	l = −13→13
25915 measured 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)] = 0.021	Hydrogen site location: riding model
wR(F²) = 0.051	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0199P)² + 0.7898P] where P = (F_o² + 2F_c²)/3
3982 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[PdBr₂(C₁₉H₁₇P)₂]	γ = 60.312 (2)°
M_r = 818.81	V = 824.54 (6) Å³
Triclinic, P1	Z = 1
a = 10.0321 (4) Å	Mo Kα radiation
b = 10.0521 (4) Å	µ = 3.11 mm⁻¹
c = 10.2967 (4) Å	T = 100 K
α = 70.876 (2)°	0.33 × 0.11 × 0.09 mm
β = 68.288 (2)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	3982 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3621 reflections with I > 2σ(I)
T_min = 0.427, T_max = 0.767	R_int = 0.029
25915 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.051	H-atom parameters constrained
S = 1.04	Δρ_max = 0.79 e Å⁻³
3982 reflections	Δρ_min = −0.46 e Å⁻³
196 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
Pd	0.5000	0.5000	0.5000	0.01341 (5)
Br	0.39230 (2)	0.78196 (2)	0.45123 (2)	0.02035 (6)
P	0.28802 (5)	0.49477 (5)	0.69762 (5)	0.01335 (9)
C11	0.3682 (2)	0.3708 (2)	0.84911 (18)	0.0139 (3)
C12	0.4892 (2)	0.3878 (2)	0.8690 (2)	0.0189 (4)
H12	0.5284	0.4573	0.8035	0.023*
C13	0.5507 (2)	0.3014 (2)	0.9859 (2)	0.0195 (4)
H13	0.6301	0.3149	0.9986	0.023*
C14	0.4963 (2)	0.1951 (2)	1.0847 (2)	0.0195 (4)
C15	0.3776 (2)	0.1772 (2)	1.0628 (2)	0.0210 (4)
H15	0.3408	0.1053	1.1267	0.025*
C16	0.3131 (2)	0.2648 (2)	0.9470 (2)	0.0178 (4)
H16	0.2327	0.2523	0.9351	0.021*
C141	0.5660 (3)	0.1007 (3)	1.2101 (2)	0.0332 (5)
H14A	0.5145	0.0339	1.2670	0.050*
H14B	0.5504	0.1693	1.2662	0.050*
H14C	0.6774	0.0386	1.1772	0.050*
C21	0.1532 (2)	0.4290 (2)	0.68471 (19)	0.0160 (3)
C22	0.2059 (2)	0.3178 (2)	0.6032 (2)	0.0235 (4)
H22	0.3122	0.2743	0.5549	0.028*
C23	0.1014 (3)	0.2714 (3)	0.5934 (2)	0.0281 (5)
H23	0.1386	0.1952	0.5404	0.034*
C24	−0.0579 (2)	0.3376 (2)	0.6621 (2)	0.0229 (4)
H24	−0.1280	0.3071	0.6543	0.027*
C25	−0.1120 (2)	0.4490 (2)	0.7422 (2)	0.0225 (4)
H25	−0.2192	0.4945	0.7878	0.027*
C26	−0.0077 (2)	0.4938 (2)	0.7553 (2)	0.0202 (4)
H26	−0.0449	0.5673	0.8114	0.024*
C31	0.1493 (2)	0.6787 (2)	0.75882 (19)	0.0144 (3)
C32	0.0568 (2)	0.8003 (2)	0.6700 (2)	0.0181 (4)
H32	0.0697	0.7872	0.5801	0.022*
C33	−0.0535 (2)	0.9396 (2)	0.7151 (2)	0.0218 (4)
H33	−0.1149	1.0196	0.6558	0.026*
C34	−0.0728 (2)	0.9604 (2)	0.8489 (2)	0.0224 (4)
H34	−0.1464	1.0545	0.8788	0.027*
C35	0.0175 (2)	0.8410 (2)	0.9375 (2)	0.0202 (4)
H35	0.0041	0.8547	1.0274	0.024*
C36	0.1286 (2)	0.7006 (2)	0.89275 (19)	0.0160 (3)
H36	0.1892	0.6208	0.9527	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd	0.01211 (9)	0.01332 (9)	0.01158 (9)	−0.00500 (7)	−0.00154 (7)	−0.00073 (7)
Br	0.01631 (9)	0.01435 (9)	0.02261 (10)	−0.00509 (7)	−0.00119 (7)	−0.00071 (7)
P	0.0124 (2)	0.0147 (2)	0.0114 (2)	−0.00587 (17)	−0.00238 (16)	−0.00109 (16)
C11	0.0122 (8)	0.0143 (8)	0.0127 (8)	−0.0038 (7)	−0.0030 (6)	−0.0027 (6)
C12	0.0188 (9)	0.0186 (9)	0.0207 (9)	−0.0112 (7)	−0.0061 (7)	0.0014 (7)
C13	0.0189 (9)	0.0206 (9)	0.0229 (10)	−0.0094 (8)	−0.0088 (7)	−0.0030 (8)
C14	0.0199 (9)	0.0182 (9)	0.0178 (9)	−0.0057 (7)	−0.0071 (7)	−0.0016 (7)
C15	0.0210 (9)	0.0222 (10)	0.0191 (9)	−0.0130 (8)	−0.0051 (7)	0.0035 (7)
C16	0.0158 (8)	0.0197 (9)	0.0183 (9)	−0.0096 (7)	−0.0046 (7)	−0.0003 (7)
C141	0.0392 (13)	0.0362 (13)	0.0271 (11)	−0.0181 (11)	−0.0190 (10)	0.0065 (10)
C21	0.0177 (9)	0.0173 (9)	0.0138 (8)	−0.0090 (7)	−0.0068 (7)	0.0021 (7)
C22	0.0188 (9)	0.0258 (10)	0.0261 (10)	−0.0065 (8)	−0.0061 (8)	−0.0095 (8)
C23	0.0297 (11)	0.0280 (11)	0.0338 (12)	−0.0112 (9)	−0.0117 (9)	−0.0119 (9)
C24	0.0278 (10)	0.0268 (10)	0.0216 (10)	−0.0166 (9)	−0.0132 (8)	0.0028 (8)
C25	0.0198 (9)	0.0285 (10)	0.0198 (10)	−0.0140 (8)	−0.0048 (8)	0.0008 (8)
C26	0.0202 (9)	0.0249 (10)	0.0169 (9)	−0.0113 (8)	−0.0024 (7)	−0.0053 (8)
C31	0.0111 (8)	0.0160 (8)	0.0155 (8)	−0.0073 (7)	−0.0009 (6)	−0.0024 (7)
C32	0.0161 (8)	0.0214 (9)	0.0151 (9)	−0.0082 (7)	−0.0039 (7)	−0.0007 (7)
C33	0.0158 (9)	0.0179 (9)	0.0265 (10)	−0.0063 (7)	−0.0061 (8)	0.0015 (8)
C34	0.0168 (9)	0.0174 (9)	0.0306 (11)	−0.0067 (8)	−0.0014 (8)	−0.0079 (8)
C35	0.0194 (9)	0.0238 (10)	0.0213 (9)	−0.0115 (8)	−0.0015 (7)	−0.0087 (8)
C36	0.0142 (8)	0.0187 (9)	0.0169 (9)	−0.0095 (7)	−0.0041 (7)	−0.0012 (7)

Geometric parameters (Å, º) top

Pd—P	2.3462 (5)	C21—C26	1.399 (3)
Pd—Pⁱ	2.3462 (5)	C22—C23	1.387 (3)
Pd—Brⁱ	2.4266 (2)	C22—H22	0.9300
Pd—Br	2.4266 (2)	C23—C24	1.384 (3)
P—C11	1.8150 (18)	C23—H23	0.9300
P—C31	1.8217 (18)	C24—C25	1.379 (3)
P—C21	1.8331 (19)	C24—H24	0.9300
C11—C16	1.387 (3)	C25—C26	1.388 (3)
C11—C12	1.399 (2)	C25—H25	0.9300
C12—C13	1.385 (3)	C26—H26	0.9300
C12—H12	0.9300	C31—C36	1.391 (3)
C13—C14	1.389 (3)	C31—C32	1.401 (3)
C13—H13	0.9300	C32—C33	1.383 (3)
C14—C15	1.392 (3)	C32—H32	0.9300
C14—C141	1.505 (3)	C33—C34	1.389 (3)
C15—C16	1.391 (3)	C33—H33	0.9300
C15—H15	0.9300	C34—C35	1.383 (3)
C16—H16	0.9300	C34—H34	0.9300
C141—H14A	0.9600	C35—C36	1.391 (3)
C141—H14B	0.9600	C35—H35	0.9300
C141—H14C	0.9600	C36—H36	0.9300
C21—C22	1.390 (3)

P—Pd—Pⁱ	180.0	C22—C21—C26	118.53 (17)
P—Pd—Brⁱ	86.472 (12)	C22—C21—P	121.58 (14)
Pⁱ—Pd—Brⁱ	93.528 (12)	C26—C21—P	119.87 (14)
P—Pd—Br	93.528 (12)	C23—C22—C21	120.60 (19)
Pⁱ—Pd—Br	86.472 (12)	C23—C22—H22	119.7
Brⁱ—Pd—Br	180.0	C21—C22—H22	119.7
C11—P—C31	103.51 (8)	C24—C23—C22	120.5 (2)
C11—P—C21	107.56 (8)	C24—C23—H23	119.8
C31—P—C21	101.59 (8)	C22—C23—H23	119.8
C11—P—Pd	108.36 (6)	C25—C24—C23	119.51 (19)
C31—P—Pd	116.57 (6)	C25—C24—H24	120.2
C21—P—Pd	118.01 (6)	C23—C24—H24	120.2
C16—C11—C12	118.91 (16)	C24—C25—C26	120.46 (19)
C16—C11—P	123.69 (14)	C24—C25—H25	119.8
C12—C11—P	117.36 (14)	C26—C25—H25	119.8
C13—C12—C11	120.18 (17)	C25—C26—C21	120.41 (18)
C13—C12—H12	119.9	C25—C26—H26	119.8
C11—C12—H12	119.9	C21—C26—H26	119.8
C12—C13—C14	121.38 (17)	C36—C31—C32	118.96 (17)
C12—C13—H13	119.3	C36—C31—P	122.06 (14)
C14—C13—H13	119.3	C32—C31—P	118.94 (14)
C13—C14—C15	118.01 (17)	C33—C32—C31	120.42 (18)
C13—C14—C141	120.66 (18)	C33—C32—H32	119.8
C15—C14—C141	121.32 (18)	C31—C32—H32	119.8
C16—C15—C14	121.24 (18)	C32—C33—C34	120.13 (18)
C16—C15—H15	119.4	C32—C33—H33	119.9
C14—C15—H15	119.4	C34—C33—H33	119.9
C11—C16—C15	120.26 (17)	C35—C34—C33	119.91 (18)
C11—C16—H16	119.9	C35—C34—H34	120.0
C15—C16—H16	119.9	C33—C34—H34	120.0
C14—C141—H14A	109.5	C34—C35—C36	120.19 (18)
C14—C141—H14B	109.5	C34—C35—H35	119.9
H14A—C141—H14B	109.5	C36—C35—H35	119.9
C14—C141—H14C	109.5	C31—C36—C35	120.38 (17)
H14A—C141—H14C	109.5	C31—C36—H36	119.8
H14B—C141—H14C	109.5	C35—C36—H36	119.8

Brⁱ—Pd—P—C11	54.51 (6)	C11—P—C21—C26	90.47 (16)
Br—Pd—P—C11	−125.49 (6)	C31—P—C21—C26	−17.89 (17)
Brⁱ—Pd—P—C31	170.70 (7)	Pd—P—C21—C26	−146.67 (13)
Br—Pd—P—C31	−9.30 (7)	C26—C21—C22—C23	−0.6 (3)
Brⁱ—Pd—P—C21	−67.94 (7)	P—C21—C22—C23	−179.11 (16)
Br—Pd—P—C21	112.06 (7)	C21—C22—C23—C24	1.5 (3)
C31—P—C11—C16	97.53 (16)	C22—C23—C24—C25	−0.9 (3)
C21—P—C11—C16	−9.49 (18)	C23—C24—C25—C26	−0.6 (3)
Pd—P—C11—C16	−138.11 (14)	C24—C25—C26—C21	1.5 (3)
C31—P—C11—C12	−80.59 (15)	C22—C21—C26—C25	−0.9 (3)
C21—P—C11—C12	172.39 (14)	P—C21—C26—C25	177.67 (15)
Pd—P—C11—C12	43.78 (15)	C11—P—C31—C36	1.98 (17)
C16—C11—C12—C13	−1.0 (3)	C21—P—C31—C36	113.45 (15)
P—C11—C12—C13	177.24 (15)	Pd—P—C31—C36	−116.86 (14)
C11—C12—C13—C14	0.9 (3)	C11—P—C31—C32	−175.85 (14)
C12—C13—C14—C15	0.1 (3)	C21—P—C31—C32	−64.39 (16)
C12—C13—C14—C141	179.2 (2)	Pd—P—C31—C32	65.30 (15)
C13—C14—C15—C16	−1.1 (3)	C36—C31—C32—C33	−0.1 (3)
C141—C14—C15—C16	179.83 (19)	P—C31—C32—C33	177.80 (14)
C12—C11—C16—C15	0.0 (3)	C31—C32—C33—C34	0.4 (3)
P—C11—C16—C15	−178.07 (15)	C32—C33—C34—C35	−0.6 (3)
C14—C15—C16—C11	1.0 (3)	C33—C34—C35—C36	0.5 (3)
C11—P—C21—C22	−91.04 (17)	C32—C31—C36—C35	0.0 (3)
C31—P—C21—C22	160.60 (16)	P—C31—C36—C35	−177.80 (14)
Pd—P—C21—C22	31.82 (18)	C34—C35—C36—C31	−0.2 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···Br	0.93	2.99	3.2380 (18)	97
C33—H33···Brⁱⁱ	0.93	2.88	3.7498 (19)	157
C22—H22···Brⁱ	0.93	2.71	3.501 (2)	144

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

Experimental details

Crystal data
Chemical formula	[PdBr₂(C₁₉H₁₇P)₂]
M_r	818.81
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.0321 (4), 10.0521 (4), 10.2967 (4)
α, β, γ (°)	70.876 (2), 68.288 (2), 60.312 (2)
V (Å³)	824.54 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.11
Crystal size (mm)	0.33 × 0.11 × 0.09

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.427, 0.767
No. of measured, independent and observed [I > 2σ(I)] reflections	25915, 3982, 3621
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.051, 1.04
No. of reflections	3982
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.46

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···Brⁱ	0.93	2.88	3.7498 (19)	157.2
C22—H22···Brⁱⁱ	0.93	2.71	3.501 (2)	143.7

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

Acknowledgements

Financial assistance from the University of the Free State is gratefully acknowledged. Part of this material is based on work supported by the South African National Research Foundation (NRF) under grant No. GUN 2068915.

References

Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). SAINT-Plus (including XPREP). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steyl, G., Kirsten, L. & Roodt, A. (2006). Acta Cryst. E62, m1705–m1707. Web of Science CSD CrossRef IUCr Journals Google Scholar