2-[4-(Methyl­sulfan­yl)phen­yl]naphtho[1,8-de][1,3,2]diaza­borinane

Slabber, C.A.; Akerman, M.P.; Robinson, R.S.

doi:10.1107/S1600536811014693

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1338

doi:10.1107/S1600536811014693

Open

access

2-[4-(Methylsulfanyl)phenyl]naphtho[1,8-de][1,3,2]diazaborinane

Cathryn A. Slabber,^a Matthew P. Akerman ^a and Ross S. Robinson ^a ^*

^aWarren Research Laboratory, School of Chemistry, University of KwaZulu Natal, Private Bag X01, Scottsville, Pietermaritzburg 3209, South Africa
^*Correspondence e-mail: robinsonr@ukzn.ac.za

(Received 24 March 2011; accepted 19 April 2011; online 7 May 2011)

The title compound, C₁₇H₁₅BN₂S, is one member in a series of diazaborinanes featuring substitution at the 1-, 2- and 3-positions in the nitrogen–boron heterocycle. The dihedral angle between the mean planes of the naphthalene and phenyl ring systems is 19.86 (6)°. In the crystal structure, two C—H⋯π interactions link the molecules into sheets which lie parallel to the bc plane. There is a π–π interaction between each pair of centrosymmetrically related sheets [centroid–centroid distance = 3.5922 (8) Å].

Related literature

For the synthesis of the title compound, see: Slabber (2011 ). For the structures of related compounds and luminescence studies, see: Weber et al. (2009 ).

Experimental

Crystal data

C₁₇H₁₅BN₂S
M_r = 290.18
Monoclinic, P 2₁ /c
a = 13.7594 (6) Å
b = 9.0545 (3) Å
c = 12.7830 (5) Å
β = 113.411 (5)°
V = 1461.46 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur 2 CCD diffractometer
Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.919, T_max = 0.939
14782 measured reflections
4709 independent reflections
2774 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.149
S = 0.98
4709 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5–C9 ring and Cg3 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg3ⁱ	0.93	2.75	3.5178 (18)	141
C12—H12⋯Cg2ⁱⁱ	0.93	2.82	3.6122 (17)	144
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) $[x, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON, SHELXL97 and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014693/lw2059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014693/lw2059Isup2.hkl

checkCIF report

Comment top

C₁₇H₁₅BN₂S, is one compound in a series of diazaborinanes featuring substitution at the 1, 2 and 3 positions in the nitrogen–boron heterocycle. The dihedral angle between the mean planes of the naphthalene and the phenyl ring systems is 19.86 (6)°. The atoms N1, B1 and N2 lie at 0.053 (2) Å, 0.084 (2) Å and 0.017 (2) Å respectively above the mean plane of the naphthalene ring.

The H atoms attached to the N atoms are unavailable for hydrogen-bonding due to their positions in the molecule.

The supramolecular structure is determined by the C2—H2···Cg3(x, 0.5 - y, -0.5 + z) and the C12—H12···Cg2(x, -0.5 - y, 0.5 + z), where Cg3 is the centroid of the phenyl ring containing C11 and Cg2 is the centroid of the phenyl ring containing C8. These link the molecules into sheets which lie in the bc plane.

There is a π–π interaction between the centrosymmetrically related phenyl rings, containing C8, at (x, y, z) and (1 - x, -y, -z). The centroid-to-centroid distance is 3.5922 (8) Å, with a perpendicular spacing between the planes of 3.3883 (6) Å and a slippage of 1.193 Å.

Related literature top

For the synthesis of the title compound, see: Slabber (2011). For the structures of related compounds and luminescence studies, see: Weber et al. (2009).

Experimental top

To a solution of 1,8-diaminonaphthalene in toluene (4.11 mmol in 50 ml, 0.82 M) (Slabber, 2011) was added the 4-(methylthio)phenylboronic acid (4.11 mmol) in one portion. The round-bottomed flask was equipped with a Dean and Stark trap, and the solution was stirred and heated at 110°C for 3 h. The solvent was removed in vacuo and column chromatography of the crude solid on silica eluting with CH₂Cl₂ yielded yellow crystalline material in a yield of 65%. Crystals suitable for X-ray diffraction analysis were grown from CH₂Cl₂ at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. A view of the molecule showing the numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

2-[4-(Methylsulfanyl)phenyl]naphtho[1,8-de][1,3,2]diazaborinane top

Crystal data top

C₁₇H₁₅BN₂S	F(000) = 608
M_r = 290.18	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5105 reflections
a = 13.7594 (6) Å	θ = 2.8–32.0°
b = 9.0545 (3) Å	µ = 0.21 mm⁻¹
c = 12.7830 (5) Å	T = 296 K
β = 113.411 (5)°	Prismatic, yellow
V = 1461.46 (10) Å³	0.40 × 0.40 × 0.30 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur 2 CCD diffractometer	4709 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 8.4190 pixels mm^-1	θ_max = 32.1°, θ_min = 2.8°
ω scans	h = −19→20
Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2008)	k = −12→12
T_min = 0.919, T_max = 0.939	l = −16→18
14782 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0834P)²] where P = (F_o² + 2F_c²)/3
4709 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₇H₁₅BN₂S	V = 1461.46 (10) Å³
M_r = 290.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7594 (6) Å	µ = 0.21 mm⁻¹
b = 9.0545 (3) Å	T = 296 K
c = 12.7830 (5) Å	0.40 × 0.40 × 0.30 mm
β = 113.411 (5)°

Data collection top

Oxford Diffraction Xcalibur 2 CCD diffractometer	4709 independent reflections
Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2008)	2774 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.939	R_int = 0.033
14782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.42 e Å⁻³
4709 reflections	Δρ_min = −0.49 e Å⁻³
199 parameters

Special details top

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 > 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
S1	0.06634 (4)	0.07477 (6)	0.41647 (4)	0.07016 (19)
N1	0.23358 (10)	0.04869 (14)	−0.03349 (11)	0.0461 (3)
H1A	0.1893 (14)	0.1126 (19)	−0.0463 (14)	0.055*
N2	0.34252 (10)	−0.14141 (14)	0.08645 (10)	0.0444 (3)
H2A	0.3614 (13)	−0.1995 (19)	0.1435 (14)	0.053*
C1	0.28153 (11)	0.03270 (15)	−0.11059 (12)	0.0402 (3)
C2	0.25289 (13)	0.11684 (18)	−0.20761 (13)	0.0509 (4)
H2	0.1989	0.1861	−0.2242	0.061*
C3	0.30433 (14)	0.09910 (17)	−0.28158 (13)	0.0534 (4)
H3	0.2833	0.1558	−0.3476	0.064*
C4	0.38422 (13)	0.00088 (17)	−0.25892 (13)	0.0485 (4)
H4	0.4181	−0.0077	−0.3087	0.058*
C5	0.49989 (12)	−0.19240 (16)	−0.13262 (12)	0.0447 (3)
H5	0.5358	−0.2034	−0.1803	0.054*
C6	0.52808 (12)	−0.27612 (16)	−0.03688 (12)	0.0461 (3)
H6	0.5829	−0.3440	−0.0203	0.055*
C7	0.47646 (12)	−0.26238 (16)	0.03701 (12)	0.0441 (3)
H7	0.4970	−0.3210	0.1020	0.053*
C8	0.39514 (11)	−0.16235 (14)	0.01405 (11)	0.0382 (3)
C9	0.36357 (11)	−0.07342 (14)	−0.08561 (11)	0.0366 (3)
C10	0.41675 (11)	−0.08885 (14)	−0.16042 (11)	0.0393 (3)
C11	0.21019 (11)	−0.00769 (16)	0.15450 (12)	0.0417 (3)
C12	0.25773 (12)	−0.05279 (17)	0.26845 (13)	0.0485 (4)
H12	0.3227	−0.1011	0.2935	0.058*
C13	0.21171 (13)	−0.02803 (18)	0.34438 (14)	0.0505 (4)
H13	0.2462	−0.0587	0.4196	0.061*
C14	0.11401 (11)	0.04254 (16)	0.31007 (13)	0.0444 (3)
C15	0.06397 (11)	0.08679 (16)	0.19740 (13)	0.0454 (3)
H15	−0.0018	0.1327	0.1724	0.054*
C16	0.11204 (11)	0.06258 (16)	0.12205 (13)	0.0448 (3)
H16	0.0777	0.0943	0.0470	0.054*
C17	−0.05682 (14)	0.1664 (2)	0.34505 (16)	0.0674 (5)
H17A	−0.0453	0.2571	0.3128	0.101*
H17B	−0.0882	0.1875	0.3984	0.101*
H17C	−0.1034	0.1042	0.2854	0.101*
B1	0.26262 (13)	−0.03403 (18)	0.06810 (14)	0.0412 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0687 (3)	0.0942 (4)	0.0586 (3)	0.0245 (3)	0.0370 (2)	0.0095 (2)
N1	0.0447 (7)	0.0488 (7)	0.0469 (7)	0.0105 (5)	0.0205 (6)	0.0060 (6)
N2	0.0530 (7)	0.0436 (7)	0.0412 (7)	0.0061 (5)	0.0237 (6)	0.0095 (5)
C1	0.0423 (7)	0.0380 (7)	0.0377 (7)	−0.0020 (6)	0.0133 (6)	−0.0009 (5)
C2	0.0560 (9)	0.0479 (9)	0.0456 (8)	0.0103 (7)	0.0167 (7)	0.0085 (7)
C3	0.0677 (11)	0.0499 (9)	0.0391 (8)	0.0042 (8)	0.0174 (7)	0.0095 (6)
C4	0.0664 (10)	0.0447 (8)	0.0380 (8)	−0.0024 (7)	0.0245 (7)	−0.0008 (6)
C5	0.0523 (9)	0.0437 (8)	0.0417 (8)	−0.0027 (6)	0.0226 (7)	−0.0071 (6)
C6	0.0487 (8)	0.0412 (8)	0.0477 (8)	0.0056 (6)	0.0182 (7)	−0.0043 (6)
C7	0.0527 (9)	0.0390 (7)	0.0399 (7)	0.0046 (6)	0.0177 (7)	0.0038 (6)
C8	0.0430 (7)	0.0346 (7)	0.0369 (7)	−0.0035 (5)	0.0158 (6)	−0.0015 (5)
C9	0.0405 (7)	0.0334 (7)	0.0331 (6)	−0.0058 (5)	0.0115 (5)	−0.0041 (5)
C10	0.0465 (8)	0.0356 (7)	0.0356 (7)	−0.0073 (6)	0.0163 (6)	−0.0066 (5)
C11	0.0407 (7)	0.0415 (7)	0.0438 (8)	−0.0018 (6)	0.0179 (6)	−0.0002 (6)
C12	0.0443 (8)	0.0541 (9)	0.0484 (8)	0.0107 (7)	0.0196 (7)	0.0055 (7)
C13	0.0499 (9)	0.0579 (9)	0.0445 (8)	0.0091 (7)	0.0196 (7)	0.0068 (7)
C14	0.0447 (8)	0.0415 (8)	0.0500 (8)	−0.0011 (6)	0.0220 (7)	−0.0008 (6)
C15	0.0368 (7)	0.0488 (8)	0.0488 (8)	0.0026 (6)	0.0152 (6)	0.0010 (6)
C16	0.0409 (7)	0.0499 (8)	0.0407 (8)	−0.0019 (6)	0.0132 (6)	0.0012 (6)
C17	0.0618 (11)	0.0654 (11)	0.0844 (13)	0.0100 (9)	0.0391 (10)	−0.0003 (10)
B1	0.0405 (8)	0.0420 (9)	0.0414 (8)	−0.0037 (6)	0.0166 (7)	−0.0013 (6)

Geometric parameters (Å, º) top

S1—C14	1.7534 (15)	C6—H6	0.9300
S1—C17	1.7789 (18)	C7—C8	1.3775 (19)
N1—C1	1.3944 (18)	C7—H7	0.9300
N1—B1	1.412 (2)	C8—C9	1.4213 (18)
N1—H1A	0.808 (17)	C9—C10	1.4231 (18)
N2—C8	1.3961 (17)	C11—C16	1.398 (2)
N2—B1	1.416 (2)	C11—C12	1.400 (2)
N2—H2A	0.852 (17)	C11—B1	1.559 (2)
C1—C2	1.373 (2)	C12—C13	1.372 (2)
C1—C9	1.4188 (19)	C12—H12	0.9300
C2—C3	1.398 (2)	C13—C14	1.393 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.353 (2)	C14—C15	1.386 (2)
C3—H3	0.9300	C15—C16	1.385 (2)
C4—C10	1.414 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.359 (2)	C17—H17A	0.9600
C5—C10	1.411 (2)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.3948 (19)

C14—S1—C17	104.67 (8)	C1—C9—C10	119.39 (12)
C1—N1—B1	123.67 (13)	C8—C9—C10	119.41 (12)
C1—N1—H1A	117.5 (12)	C5—C10—C4	122.98 (13)
B1—N1—H1A	118.8 (12)	C5—C10—C9	118.55 (12)
C8—N2—B1	123.82 (12)	C4—C10—C9	118.48 (13)
C8—N2—H2A	115.0 (11)	C16—C11—C12	116.00 (13)
B1—N2—H2A	121.2 (11)	C16—C11—B1	121.58 (13)
C2—C1—N1	122.28 (13)	C12—C11—B1	122.42 (13)
C2—C1—C9	119.75 (13)	C13—C12—C11	122.17 (14)
N1—C1—C9	117.96 (12)	C13—C12—H12	118.9
C1—C2—C3	120.43 (14)	C11—C12—H12	118.9
C1—C2—H2	119.8	C12—C13—C14	120.76 (14)
C3—C2—H2	119.8	C12—C13—H13	119.6
C4—C3—C2	121.17 (14)	C14—C13—H13	119.6
C4—C3—H3	119.4	C15—C14—C13	118.60 (13)
C2—C3—H3	119.4	C15—C14—S1	124.99 (11)
C3—C4—C10	120.75 (14)	C13—C14—S1	116.35 (12)
C3—C4—H4	119.6	C16—C15—C14	119.96 (13)
C10—C4—H4	119.6	C16—C15—H15	120.0
C6—C5—C10	120.69 (13)	C14—C15—H15	120.0
C6—C5—H5	119.7	C15—C16—C11	122.50 (14)
C10—C5—H5	119.7	C15—C16—H16	118.7
C5—C6—C7	121.36 (14)	C11—C16—H16	118.7
C5—C6—H6	119.3	S1—C17—H17A	109.5
C7—C6—H6	119.3	S1—C17—H17B	109.5
C8—C7—C6	120.23 (13)	H17A—C17—H17B	109.5
C8—C7—H7	119.9	S1—C17—H17C	109.5
C6—C7—H7	119.9	H17A—C17—H17C	109.5
C7—C8—N2	122.63 (12)	H17B—C17—H17C	109.5
C7—C8—C9	119.77 (12)	N1—B1—N2	115.72 (13)
N2—C8—C9	117.58 (12)	N1—B1—C11	121.92 (13)
C1—C9—C8	121.19 (12)	N2—B1—C11	122.36 (13)

B1—N1—C1—C2	−178.71 (15)	C1—C9—C10—C5	178.43 (12)
B1—N1—C1—C9	0.4 (2)	C8—C9—C10—C5	−0.22 (18)
N1—C1—C2—C3	178.83 (14)	C1—C9—C10—C4	−1.23 (19)
C9—C1—C2—C3	−0.3 (2)	C8—C9—C10—C4	−179.88 (12)
C1—C2—C3—C4	−1.0 (2)	C16—C11—C12—C13	−0.8 (2)
C2—C3—C4—C10	1.2 (2)	B1—C11—C12—C13	179.34 (14)
C10—C5—C6—C7	−0.2 (2)	C11—C12—C13—C14	0.7 (2)
C5—C6—C7—C8	−0.1 (2)	C12—C13—C14—C15	0.2 (2)
C6—C7—C8—N2	−178.36 (13)	C12—C13—C14—S1	−177.34 (12)
C6—C7—C8—C9	0.3 (2)	C17—S1—C14—C15	2.01 (16)
B1—N2—C8—C7	176.50 (14)	C17—S1—C14—C13	179.41 (13)
B1—N2—C8—C9	−2.2 (2)	C13—C14—C15—C16	−1.0 (2)
C2—C1—C9—C8	−179.98 (13)	S1—C14—C15—C16	176.34 (11)
N1—C1—C9—C8	0.86 (19)	C14—C15—C16—C11	0.9 (2)
C2—C1—C9—C10	1.4 (2)	C12—C11—C16—C15	0.0 (2)
N1—C1—C9—C10	−177.77 (12)	B1—C11—C16—C15	179.86 (13)
C7—C8—C9—C1	−178.74 (12)	C1—N1—B1—N2	−2.4 (2)
N2—C8—C9—C1	−0.03 (19)	C1—N1—B1—C11	177.28 (13)
C7—C8—C9—C10	−0.11 (19)	C8—N2—B1—N1	3.3 (2)
N2—C8—C9—C10	178.60 (12)	C8—N2—B1—C11	−176.37 (13)
C6—C5—C10—C4	−179.96 (14)	C16—C11—B1—N1	20.3 (2)
C6—C5—C10—C9	0.4 (2)	C12—C11—B1—N1	−159.84 (15)
C3—C4—C10—C5	−179.68 (14)	C16—C11—B1—N2	−160.00 (14)
C3—C4—C10—C9	0.0 (2)	C12—C11—B1—N2	19.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3ⁱ	0.93	2.75	3.5178 (18)	141
C12—H12···Cg2ⁱⁱ	0.93	2.82	3.6122 (17)	144

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) x, −y−3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BN₂S
M_r	290.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.7594 (6), 9.0545 (3), 12.7830 (5)
β (°)	113.411 (5)
V (Å³)	1461.46 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur 2 CCD diffractometer
Absorption correction	Multi-scan CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.919, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	14782, 4709, 2774
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.747

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.149, 0.98
No. of reflections	4709
No. of parameters	199
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.49

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3ⁱ	0.93	2.75	3.5178 (18)	141
C12—H12···Cg2ⁱⁱ	0.93	2.82	3.6122 (17)	144

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) x, −y−3/2, z−1/2.

Acknowledgements

The authors thank Professor O. Q. Munro and Mr C. R. Wilson (University of KwaZulu-Natal) for the data collection and structure refinement.

References

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Slabber, C. A. (2011). Ultrastabilized Boranes: A Study into the Synthesis, Structure and Reactivities of Heterosubstituted Organoboranes. MSc Thesis, University of KwaZulu Natal, South Africa. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Weber, L., Werner, V., Fox, M. A., Marder, R. T. S., Schwedler, S., Brockhinke, A., Stammler, H.-G. & Neumann, B. (2009). Dalton Trans. pp. 1339–1351. CrossRef Google Scholar