Diphenyl(pyridin-2-yl)­phosphane selenide

Davis, W.L.; Muller, A.

doi:10.1107/S160053681204007X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3073

doi:10.1107/S160053681204007X

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Diphenyl(pyridin-2-yl)phosphane selenide

Wade L. Davis ^a and Alfred Muller ^a ^*

^aResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
^*Correspondence e-mail: mullera@uj.ac.za

(Received 30 July 2012; accepted 21 September 2012; online 6 October 2012)

In the title compound, C₁₇H₁₄NPSe, the P atom has a distorted tetrahedral environment resulting in an effective cone angle of 163°. In the crystal, C—H⋯Se/N/π interactions are observed.

Related literature

For background to phosphorus- and selenium-containing ligands, see: Muller et al. (2006 , 2008 ). For the free phosphine of the title compound, see: Charland et al. (1989 ). For background on cone angles, see: Otto (2001 ); Tolman (1977 ). For details of the conformational fit of the two molecules using Mercury, see: Macrae et al. (2008 ); Weng et al. (2008a ,b ).

Experimental

Crystal data

C₁₇H₁₄NPSe
M_r = 342.22
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.8092 (4) Å
b = 9.4066 (4) Å
c = 18.2661 (7) Å
V = 1513.61 (11) Å³
Z = 4
Cu Kα radiation
μ = 4.25 mm⁻¹
T = 100 K
0.24 × 0.17 × 0.12 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.429, T_max = 0.629
6004 measured reflections
2501 independent reflections
2461 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.053
S = 0.87
2501 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), with 992 Friedel pairs
Flack parameter: 0.053 (19)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Se1	0.95	2.87	3.427 (3)	118
C8—H8⋯N1	0.95	2.57	3.111 (3)	116
C14—H14⋯Se1	0.95	2.96	3.472 (2)	115
C5—H5⋯Se1ⁱ	0.95	3.07	3.923 (3)	150
C16—H16⋯Se1ⁱⁱ	0.95	3.26	3.938 (3)	130
C11—H11⋯Cg1ⁱⁱⁱ	0.95	2.77	3.630 (3)	151
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: publCIF (Westrip, 2010 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204007X/kp2438sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204007X/kp2438Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204007X/kp2438Isup3.cml

checkCIF report

Comment top

As part our systematic investigation on the steric and electronic properties of phosphorus containing ligands, we are also utilizing the ¹J(³¹P-⁷⁷Se) multi-nuclear NMR coupling in Se—P bond as a probe (see Muller et al., 2008). The advantage of this approach is that there is no steric crowding effect, albeit crystal packing effects, as normally found in transition metal complexes with bulky ligands, e.g. in trans-[Rh(CO)Cl{P(OC₆H₅)₃}₂] cone angles variation from 156° to 167° was observed for the two phosphite ligands (Muller et al., 2006). Herein we report here the single-crystal structure of SePPh₂py, where Ph = C₆H₅ and py = C₅H₄N as part of our investigation.

Molecules of the title compound (Fig. 1) adopts a distorted tetrahedral arrangement about the P atom with average C—P—C and Se—P—C angles of 105.47° and 113.20° respectively. Describing the steric demand of phosphane ligands has been the topic of many studies and a variety of models have been developed. The Tolman cone angle (Tolman, 1977) is still the most commonly used model. Applying this model to the geometry obtained for the title compound (and adjusting the Se—P bond distance to 2.28 Å) we calculated an effective cone angle from the geometry found in the crystal structure of 163° (Otto, 2001). The angle calculated is 9° larger than that of the free phosphine (Charland et al., 1989; effective cone angle calculated as 154°), and could be ascribed to C—H···Se/N/π intra- and interactions observed in the title compound (Table 1, Fig. 2), whereas the free phosphine shows C—H···N/π interactions only. The difference in the orientation of the substituents for these two structures can be illustrated by superimposing their coordinates (Fig. 3); root mean squared deviation calculated as 0.0468 Å for P and ipso C atoms only using Mercury (Macrae et al., 2008; Weng et al., 2008a,b).

Related literature top

For background to phosphorus- and selenium-containing ligands, see: Muller et al. (2006, 2008). For the free phosphine of the title compound, see: Charland et al. (1989). For background on cone angles, see: Otto (2001); Tolman (1977). For details of the conformational fit of the two molecules using Mercury, see: Macrae et al. (2008); Weng et al. (2008a,b).

Experimental top

Diphenyl-2-pyridylphosphine and KSeCN were purchased from Sigma–Aldrich and used without purification. Eqimolar amounts of KSeCN (5.8 mg, 0.04 mmol) and the diphenylpyridylphosphine (10.5 mg, 0.04 mmol) were dissolved in the minimum amounts of methanol (10 ml). The KSeCN solution was added dropwise (5 min) to the phosphine solution with stirring at room temperature. The final solution was left to evaporate slowly until dry to give crystals suitable for a single-crystal X-ray study. Analytical data: ³¹P {H} NMR (CDCl₃, 161.99 MHz): δ = 31.47 (t, ¹J(³¹P-⁷⁷Se) = 734 Hz).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of (1). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of (1) showing the C—H···Se/N/π interactions.
	Fig. 3. Conformational similarity between the title compound (black) and the free phosphine (red).

Diphenyl(pyridin-2-yl)phosphane selenide top

Crystal data top

C₁₇H₁₄NPSe	F(000) = 688
M_r = 342.22	D_x = 1.502 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5093 reflections
a = 8.8092 (4) Å	θ = 4.8–66.6°
b = 9.4066 (4) Å	µ = 4.25 mm⁻¹
c = 18.2661 (7) Å	T = 100 K
V = 1513.61 (11) Å³	Cuboid, colourless
Z = 4	0.24 × 0.17 × 0.12 mm

Data collection top

Bruker APEX DUO 4K-CCD diffractometer	2501 independent reflections
Incoatec Quazar Multilayer Mirror monochromator	2461 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm^-1	R_int = 0.025
ϕ and ω scans	θ_max = 66.6°, θ_min = 4.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→10
T_min = 0.429, T_max = 0.629	k = −3→11
6004 measured reflections	l = −21→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.053	w = 1/[σ²(F_o²) + (0.0288P)² + 1.1995P] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max < 0.001
2501 reflections	Δρ_max = 0.43 e Å⁻³
181 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 992 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.053 (19)

Crystal data top

C₁₇H₁₄NPSe	V = 1513.61 (11) Å³
M_r = 342.22	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.8092 (4) Å	µ = 4.25 mm⁻¹
b = 9.4066 (4) Å	T = 100 K
c = 18.2661 (7) Å	0.24 × 0.17 × 0.12 mm

Data collection top

Bruker APEX DUO 4K-CCD diffractometer	2501 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2461 reflections with I > 2σ(I)
T_min = 0.429, T_max = 0.629	R_int = 0.025
6004 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.053	Δρ_max = 0.43 e Å⁻³
S = 0.87	Δρ_min = −0.27 e Å⁻³
2501 reflections	Absolute structure: Flack (1983), with 992 Friedel pairs
181 parameters	Absolute structure parameter: 0.053 (19)
0 restraints

Special details top

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 5 s/frame. A total of 287 frames were collected with a frame width of 4° covering up to θ = 66.62° with 96.7% completeness accomplished.

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
Se1	0.16691 (3)	0.13803 (3)	0.059243 (13)	0.01846 (8)
P1	0.28195 (7)	−0.00265 (7)	0.12974 (3)	0.01351 (13)
N1	0.5564 (3)	−0.0376 (2)	0.19118 (12)	0.0211 (5)
C1	0.2066 (3)	−0.0007 (3)	0.22196 (12)	0.0155 (5)
C2	0.2524 (3)	0.1080 (3)	0.26909 (13)	0.0222 (6)
H2	0.3282	0.1737	0.2541	0.027*
C3	0.1867 (3)	0.1197 (3)	0.33781 (14)	0.0279 (6)
H3	0.2185	0.1927	0.3703	0.034*
C4	0.0749 (3)	0.0250 (3)	0.35923 (14)	0.0271 (6)
H4	0.0292	0.0341	0.4061	0.033*
C5	0.0295 (3)	−0.0826 (3)	0.31256 (14)	0.0226 (6)
H5	−0.0465	−0.1479	0.3276	0.027*
C6	0.0953 (3)	−0.0952 (3)	0.24349 (14)	0.0192 (6)
H6	0.0636	−0.1687	0.2113	0.023*
C7	0.2834 (3)	−0.1863 (3)	0.09839 (13)	0.0165 (5)
C12	0.2168 (3)	−0.2192 (3)	0.03143 (13)	0.0218 (6)
H12	0.1654	−0.1481	0.0041	0.026*
C11	0.2266 (3)	−0.3580 (3)	0.00496 (13)	0.0257 (6)
H11	0.1802	−0.382	−0.0403	0.031*
C10	0.3034 (3)	−0.4608 (3)	0.04429 (14)	0.0249 (6)
H10	0.3129	−0.5543	0.0252	0.03*
C9	0.3666 (3)	−0.4276 (3)	0.11135 (15)	0.0271 (6)
H9	0.417	−0.499	0.1389	0.033*
C8	0.3567 (3)	−0.2906 (3)	0.13858 (14)	0.0216 (6)
H8	0.4001	−0.2681	0.1848	0.026*
C13	0.4816 (3)	0.0441 (3)	0.14240 (13)	0.0153 (5)
C17	0.7046 (3)	−0.0092 (3)	0.20170 (14)	0.0222 (6)
H17	0.7597	−0.0657	0.2356	0.027*
C16	0.7802 (3)	0.0985 (3)	0.16541 (14)	0.0203 (6)
H16	0.8851	0.1146	0.1741	0.024*
C15	0.7021 (3)	0.1817 (3)	0.11670 (14)	0.0221 (6)
H15	0.7518	0.2571	0.0917	0.026*
C14	0.5494 (3)	0.1544 (3)	0.10432 (13)	0.0193 (5)
H14	0.4928	0.21	0.0706	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.01952 (13)	0.01885 (13)	0.01701 (12)	0.00321 (11)	−0.00156 (10)	0.00276 (10)
P1	0.0138 (3)	0.0140 (3)	0.0127 (3)	0.0002 (3)	0.0005 (2)	0.0005 (2)
N1	0.0168 (11)	0.0207 (12)	0.0257 (11)	0.0009 (9)	−0.0010 (9)	0.0027 (9)
C1	0.0160 (13)	0.0164 (12)	0.0142 (10)	0.0031 (11)	−0.0007 (9)	0.0023 (9)
C2	0.0217 (14)	0.0247 (16)	0.0201 (13)	−0.0027 (11)	0.0031 (10)	−0.0015 (10)
C3	0.0336 (16)	0.0306 (15)	0.0196 (13)	0.0013 (15)	0.0005 (11)	−0.0057 (11)
C4	0.0285 (16)	0.0351 (17)	0.0178 (13)	0.0114 (13)	0.0059 (11)	0.0033 (11)
C5	0.0170 (13)	0.0280 (15)	0.0229 (13)	0.0036 (11)	0.0054 (11)	0.0099 (11)
C6	0.0185 (13)	0.0200 (15)	0.0193 (12)	0.0024 (11)	−0.0020 (10)	0.0028 (10)
C7	0.0141 (12)	0.0161 (13)	0.0194 (12)	−0.0012 (10)	0.0058 (10)	−0.0019 (9)
C12	0.0256 (13)	0.0230 (14)	0.0167 (12)	−0.0026 (12)	0.0021 (10)	0.0000 (10)
C11	0.0360 (14)	0.0233 (13)	0.0176 (12)	−0.0096 (14)	0.0010 (11)	−0.0032 (11)
C10	0.0329 (16)	0.0172 (13)	0.0246 (13)	−0.0034 (11)	0.0103 (11)	−0.0040 (10)
C9	0.0273 (17)	0.0213 (14)	0.0327 (15)	0.0037 (12)	0.0009 (12)	0.0000 (11)
C8	0.0216 (14)	0.0233 (13)	0.0199 (12)	−0.0015 (12)	−0.0043 (11)	−0.0036 (10)
C13	0.0142 (12)	0.0168 (13)	0.0149 (11)	0.0028 (10)	0.0030 (9)	−0.0026 (9)
C17	0.0210 (14)	0.0206 (13)	0.0250 (13)	−0.0015 (13)	−0.0041 (10)	0.0007 (11)
C16	0.0140 (12)	0.0222 (15)	0.0248 (13)	−0.0042 (11)	0.0014 (10)	−0.0057 (10)
C15	0.0191 (14)	0.0244 (14)	0.0227 (12)	−0.0061 (11)	0.0025 (10)	0.0026 (10)
C14	0.0185 (12)	0.0213 (14)	0.0179 (12)	0.0000 (12)	−0.0007 (9)	0.0002 (10)

Geometric parameters (Å, º) top

Se1—P1	2.1063 (6)	C7—C12	1.391 (3)
P1—C1	1.811 (2)	C12—C11	1.395 (4)
P1—C7	1.820 (2)	C12—H12	0.95
P1—C13	1.828 (3)	C11—C10	1.381 (4)
N1—C13	1.349 (3)	C11—H11	0.95
N1—C17	1.347 (3)	C10—C9	1.381 (4)
C1—C6	1.380 (4)	C10—H10	0.95
C1—C2	1.397 (4)	C9—C8	1.384 (4)
C2—C3	1.387 (4)	C9—H9	0.95
C2—H2	0.95	C8—H8	0.95
C3—C4	1.384 (4)	C13—C14	1.384 (4)
C3—H3	0.95	C17—C16	1.381 (4)
C4—C5	1.382 (4)	C17—H17	0.95
C4—H4	0.95	C16—C15	1.370 (4)
C5—C6	1.393 (4)	C16—H16	0.95
C5—H5	0.95	C15—C14	1.388 (4)
C6—H6	0.95	C15—H15	0.95
C7—C8	1.385 (4)	C14—H14	0.95

C1—P1—C7	107.75 (11)	C7—C12—H12	120.4
C1—P1—C13	103.46 (11)	C11—C12—H12	120.4
C7—P1—C13	105.15 (11)	C10—C11—C12	120.3 (2)
C1—P1—Se1	112.71 (8)	C10—C11—H11	119.8
C7—P1—Se1	114.04 (9)	C12—C11—H11	119.8
C13—P1—Se1	112.90 (8)	C11—C10—C9	120.0 (2)
C13—N1—C17	117.0 (2)	C11—C10—H10	120
C6—C1—C2	120.1 (2)	C9—C10—H10	120
C6—C1—P1	121.27 (19)	C10—C9—C8	120.3 (3)
C2—C1—P1	118.34 (19)	C10—C9—H9	119.9
C3—C2—C1	119.7 (2)	C8—C9—H9	119.9
C3—C2—H2	120.2	C7—C8—C9	119.9 (2)
C1—C2—H2	120.2	C7—C8—H8	120.1
C4—C3—C2	120.2 (3)	C9—C8—H8	120.1
C4—C3—H3	119.9	N1—C13—C14	123.3 (2)
C2—C3—H3	119.9	N1—C13—P1	114.59 (18)
C3—C4—C5	120.1 (2)	C14—C13—P1	122.12 (19)
C3—C4—H4	119.9	N1—C17—C16	123.0 (2)
C5—C4—H4	119.9	N1—C17—H17	118.5
C4—C5—C6	120.1 (3)	C16—C17—H17	118.5
C4—C5—H5	120	C15—C16—C17	119.2 (2)
C6—C5—H5	120	C15—C16—H16	120.4
C1—C6—C5	119.9 (2)	C17—C16—H16	120.4
C1—C6—H6	120.1	C16—C15—C14	119.1 (2)
C5—C6—H6	120.1	C16—C15—H15	120.4
C8—C7—C12	120.3 (2)	C14—C15—H15	120.4
C8—C7—P1	120.58 (19)	C13—C14—C15	118.3 (2)
C12—C7—P1	119.0 (2)	C13—C14—H14	120.8
C7—C12—C11	119.1 (3)	C15—C14—H14	120.8

C7—P1—C1—C6	−34.1 (2)	P1—C7—C12—C11	175.8 (2)
C13—P1—C1—C6	−145.1 (2)	C7—C12—C11—C10	−1.0 (4)
Se1—P1—C1—C6	92.6 (2)	C12—C11—C10—C9	2.2 (4)
C7—P1—C1—C2	152.3 (2)	C11—C10—C9—C8	−1.7 (4)
C13—P1—C1—C2	41.3 (2)	C12—C7—C8—C9	1.4 (4)
Se1—P1—C1—C2	−81.0 (2)	P1—C7—C8—C9	−175.2 (2)
C6—C1—C2—C3	0.7 (4)	C10—C9—C8—C7	−0.1 (4)
P1—C1—C2—C3	174.4 (2)	C17—N1—C13—C14	−0.7 (4)
C1—C2—C3—C4	−0.8 (4)	C17—N1—C13—P1	178.94 (19)
C2—C3—C4—C5	0.8 (4)	C1—P1—C13—N1	53.4 (2)
C3—C4—C5—C6	−0.6 (4)	C7—P1—C13—N1	−59.5 (2)
C2—C1—C6—C5	−0.5 (4)	Se1—P1—C13—N1	175.59 (16)
P1—C1—C6—C5	−174.0 (2)	C1—P1—C13—C14	−126.9 (2)
C4—C5—C6—C1	0.5 (4)	C7—P1—C13—C14	120.2 (2)
C1—P1—C7—C8	−55.0 (2)	Se1—P1—C13—C14	−4.7 (2)
C13—P1—C7—C8	54.9 (2)	C13—N1—C17—C16	0.3 (4)
Se1—P1—C7—C8	179.09 (18)	N1—C17—C16—C15	0.5 (4)
C1—P1—C7—C12	128.4 (2)	C17—C16—C15—C14	−0.9 (4)
C13—P1—C7—C12	−121.7 (2)	N1—C13—C14—C15	0.4 (4)
Se1—P1—C7—C12	2.5 (2)	P1—C13—C14—C15	−179.30 (19)
C8—C7—C12—C11	−0.8 (4)	C16—C15—C14—C13	0.5 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Se1	0.95	2.87	3.427 (3)	118
C8—H8···N1	0.95	2.57	3.111 (3)	116
C14—H14···Se1	0.95	2.96	3.472 (2)	115
C5—H5···Se1ⁱ	0.95	3.07	3.923 (3)	150
C16—H16···Se1ⁱⁱ	0.95	3.26	3.938 (3)	130
C11—H11···Cg1ⁱⁱⁱ	0.95	2.77	3.630 (3)	151

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄NPSe
M_r	342.22
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	8.8092 (4), 9.4066 (4), 18.2661 (7)
V (Å³)	1513.61 (11)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.25
Crystal size (mm)	0.24 × 0.17 × 0.12

Data collection
Diffractometer	Bruker APEX DUO 4K-CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.429, 0.629
No. of measured, independent and observed [I > 2σ(I)] reflections	6004, 2501, 2461
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.053, 0.87
No. of reflections	2501
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.27
Absolute structure	Flack (1983), with 992 Friedel pairs
Absolute structure parameter	0.053 (19)

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Se1	0.95	2.87	3.427 (3)	118.2
C8—H8···N1	0.95	2.57	3.111 (3)	116.3
C14—H14···Se1	0.95	2.96	3.472 (2)	115.4
C5—H5···Se1ⁱ	0.95	3.07	3.923 (3)	149.5
C16—H16···Se1ⁱⁱ	0.95	3.26	3.938 (3)	130.1
C11—H11···Cg1ⁱⁱⁱ	0.95	2.77	3.630 (3)	151

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

Acknowledgements

Financial assistance from the Research Fund of the University of Johannesburg is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Charland, J.-P., Roustan, J.-L. & Ansari, N. (1989). Acta Cryst. C45, 680–681. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Muller, A., Meijboom, R. & Roodt, A. (2006). J. Organomet. Chem. 691, 5794–5801. Web of Science CSD CrossRef CAS Google Scholar
Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650–657. Web of Science CSD CrossRef PubMed Google Scholar
Otto, S. (2001). Acta Cryst. C57, 793–795. 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
Tolman, C. A. (1977). Chem. Rev. 77, 313–348. CrossRef CAS Web of Science Google Scholar
Weng, Z. F., Motherwell, W. D. S., Allen, F. H. & Cole, J. M. (2008a). Acta Cryst. B64, 348–362. Web of Science CrossRef IUCr Journals Google Scholar
Weng, Z. F., Motherwell, W. D. S. & Cole, J. M. (2008b). J. Appl. Cryst. 41, 955–957. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3073

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