(4-Ethenylphen­yl)diphenyl­phosphine selenide

Phasha, Z.H.; Makhoba, S.; Muller, A.

doi:10.1107/S1600536812034289

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2690

doi:10.1107/S1600536812034289

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(4-Ethenylphenyl)diphenylphosphine selenide

Zanele H. Phasha,^a Sizwe Makhoba ^a and Alfred Muller ^a ^*

^aResearch Center 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 26 July 2012; accepted 1 August 2012; online 11 August 2012)

In the title molecule, C₁₀H₁₇PSe, the P atom has a distorted tetrahedral environment resulting in an effective cone angle of 165°. The benzene ring makes dihedral angles of 70.04 (8) and 77.28 (8)° with the phenyl rings, while the dihedral angle between the phenyl rings is 62.95 (8)°. In the crystal, molecules are linked by C—H⋯π interactions.

Related literature

For background to our investigation of the steric and electronic effects of group 15 ligands, see: Roodt et al. (2003 ); Muller et al. (2006 , 2008 ). For background to cone angles, see: Bunten et al. (2002 ); Tolman (1977 ); Otto (2001 ).

Experimental

Crystal data

C₂₀H₁₇PSe
M_r = 367.27
Monoclinic, P 2₁ /c
a = 10.5310 (7) Å
b = 11.1477 (7) Å
c = 17.2187 (9) Å
β = 124.562 (3)°
V = 1664.66 (18) Å³
Z = 4
Mo Kα radiation
μ = 2.35 mm⁻¹
T = 100 K
0.3 × 0.25 × 0.13 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.526, T_max = 0.737
20089 measured reflections
4166 independent reflections
3921 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.063
S = 1.03
4166 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 1.37 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯Cg1ⁱ	0.95	2.62	3.383 (2)	137
C3—H3⋯Cg2ⁱⁱ	0.95	2.88	3.5889 (19)	133
C12—H12⋯Cg2ⁱⁱⁱ	0.95	2.85	3.614 (2)	138
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034289/is5175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034289/is5175Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034289/is5175Isup3.cml

checkCIF report

Comment top

Various techniques such as crystallography, multi nuclear NMR and IR have been used to extensively study the transition metal phosphorous bond (Roodt et al., 2003). As part of this systematic investigation we have extended this study to selenium derivatives of the phosphorus ligands (see Muller et al., 2008). This way 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). The ¹J(³¹P-⁷⁷Se) coupling can also be used as an additional probe to obtain more information regarding the nature of the phosphorous bond. Reported as part of the above continuing study, the single-crystal structure of the phosphorus containing compound, SePPh₂(4-C₂H₃—C₆H₄), where Ph = C₆H₅ and 4-C₂H₃—C₆H₄ = 4-vinylbenzene, is reported here.

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 105.74 and 112.98°, respectively. Describing the steric demand of phosphine ligands has been the topic of many studies and a variety of models have been developed (Bunten et al., 2002). Of these 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 as described by Tolman), we calculated an effective cone angle from the geometry found in the crystal structure of 165° (Otto, 2001). Intermolecular C—H···π interactions (Table 1 and Fig. 2) are observed in the crystal.

Related literature top

For background to our investigation of the steric and electronic effects of group 15 ligands, see: Roodt et al. (2003); Muller et al. (2006, 2008). For background to cone angles, see: Bunten et al. (2002); Tolman (1977); Otto (2001).

Experimental top

Diphenylphosphino styrene and KSeCN were purchased from Sigma-Aldrich and used without purification. Eqimolar amounts of KSeCN (5.8 mg, 0.04 mmol) and the diphenylphosphino styrene (11.5 mg, 0.04 mmol) were dissolved in the minimum amounts of methanol (10 ml). The KSeCN solution was added drop wise (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: ¹H NMR (CDCl₃, 400 MHz): δ 7.74–7.68 (m, 6H), 7.45–7.42 (m, 8H), 6.75–6.68 (m, 1H), 5.82(d,J = 17.6 Hz, 1H), 5.36 (d, J = 4.8 Hz, 3H); ¹³C {H} NMR (CDCl₃, 400 MHz) δ 135.8,116.7 (ethylene), 133.0,132.9,132.7,132.6,131.6,128.6,128.5,126.3,126,2 (Ar) ³¹P {H} NMR (CDCl₃, 161.99 MHz): δ = 34.71 (t, ¹J(³¹P-⁷⁷Se) = 729 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound, showing the C—H···π interactions.

(4-Ethenylphenyl)diphenylphosphine selenide top

Crystal data top

C₂₀H₁₇PSe	F(000) = 744
M_r = 367.27	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9906 reflections
a = 10.5310 (7) Å	θ = 2.5–28.4°
b = 11.1477 (7) Å	µ = 2.35 mm⁻¹
c = 17.2187 (9) Å	T = 100 K
β = 124.562 (3)°	Plate, colourless
V = 1664.66 (18) Å³	0.3 × 0.25 × 0.13 mm
Z = 4

Data collection top

Bruker APEX DUO 4K-CCD diffractometer	4166 independent reflections
Graphite monochromator	3921 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm^-1	R_int = 0.028
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
T_min = 0.526, T_max = 0.737	k = −14→14
20089 measured reflections	l = −16→22

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.032P)² + 1.0912P] where P = (F_o² + 2F_c²)/3
4166 reflections	(Δ/σ)_max = 0.002
199 parameters	Δρ_max = 1.37 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₀H₁₇PSe	V = 1664.66 (18) Å³
M_r = 367.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5310 (7) Å	µ = 2.35 mm⁻¹
b = 11.1477 (7) Å	T = 100 K
c = 17.2187 (9) Å	0.3 × 0.25 × 0.13 mm
β = 124.562 (3)°

Data collection top

Bruker APEX DUO 4K-CCD diffractometer	4166 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3921 reflections with I > 2σ(I)
T_min = 0.526, T_max = 0.737	R_int = 0.028
20089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.03	Δρ_max = 1.37 e Å⁻³
4166 reflections	Δρ_min = −0.41 e Å⁻³
199 parameters

Special details top

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 1.5 s/frame. A total of 1478 frames were collected with a frame width of 0.5° covering up to θ = 28.40° with 99.9% 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
C1	0.32208 (15)	0.17035 (12)	0.77818 (9)	0.0137 (2)
C2	0.42929 (16)	0.09481 (13)	0.85112 (10)	0.0168 (3)
H2	0.534	0.119	0.8916	0.02*
C3	0.38312 (16)	−0.01578 (13)	0.86458 (10)	0.0179 (3)
H3	0.4572	−0.0668	0.9139	0.021*
C4	0.22952 (17)	−0.05274 (12)	0.80657 (10)	0.0165 (3)
C5	0.12331 (16)	0.02363 (13)	0.73350 (10)	0.0178 (3)
H5	0.0186	−0.0005	0.693	0.021*
C6	0.16804 (16)	0.13364 (13)	0.71908 (10)	0.0165 (3)
H6	0.0942	0.1841	0.6691	0.02*
C7	0.17416 (18)	−0.16732 (13)	0.81962 (11)	0.0222 (3)
H7	0.0663	−0.1817	0.7798	0.027*
C8	0.2598 (2)	−0.25211 (14)	0.88126 (13)	0.0269 (3)
H8A	0.3683	−0.242	0.9226	0.032*
H8B	0.2129	−0.3232	0.8842	0.032*
C9	0.58097 (15)	0.32505 (12)	0.83389 (9)	0.0151 (2)
C10	0.66759 (16)	0.24875 (14)	0.81638 (10)	0.0198 (3)
H10	0.6167	0.1951	0.7644	0.024*
C11	0.82745 (17)	0.25109 (14)	0.87468 (11)	0.0226 (3)
H11	0.8857	0.1982	0.8631	0.027*
C12	0.90255 (17)	0.33079 (15)	0.95012 (11)	0.0242 (3)
H12	1.012	0.3324	0.99	0.029*
C13	0.81748 (18)	0.40761 (15)	0.96690 (11)	0.0243 (3)
H13	0.8689	0.4629	1.0178	0.029*
C14	0.65719 (17)	0.40446 (13)	0.90988 (10)	0.0195 (3)
H14	0.5996	0.4563	0.9227	0.023*
C15	0.30934 (15)	0.32151 (12)	0.63898 (9)	0.0148 (2)
C16	0.23401 (16)	0.42233 (13)	0.58296 (10)	0.0189 (3)
H16	0.2133	0.4892	0.6084	0.023*
C17	0.18938 (18)	0.42445 (15)	0.48962 (11)	0.0238 (3)
H17	0.1383	0.4929	0.4515	0.029*
C18	0.21944 (18)	0.32687 (15)	0.45237 (11)	0.0241 (3)
H18	0.1895	0.3289	0.3889	0.029*
C19	0.29308 (17)	0.22632 (14)	0.50744 (10)	0.0216 (3)
H19	0.3136	0.1597	0.4817	0.026*
C20	0.33703 (16)	0.22300 (13)	0.60052 (10)	0.0177 (3)
H20	0.3859	0.1535	0.6379	0.021*
P1	0.37156 (4)	0.31925 (3)	0.76149 (2)	0.01286 (8)
Se1	0.270418 (17)	0.457326 (12)	0.793367 (11)	0.01969 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0185 (6)	0.0122 (6)	0.0146 (6)	−0.0004 (5)	0.0119 (5)	−0.0007 (5)
C2	0.0169 (6)	0.0158 (6)	0.0193 (6)	0.0008 (5)	0.0113 (5)	0.0007 (5)
C3	0.0205 (6)	0.0144 (6)	0.0207 (7)	0.0033 (5)	0.0130 (6)	0.0033 (5)
C4	0.0233 (7)	0.0135 (6)	0.0183 (7)	−0.0012 (5)	0.0152 (6)	−0.0012 (5)
C5	0.0188 (6)	0.0190 (7)	0.0160 (6)	−0.0039 (5)	0.0102 (5)	−0.0018 (5)
C6	0.0195 (6)	0.0165 (6)	0.0135 (6)	−0.0002 (5)	0.0094 (5)	0.0010 (5)
C7	0.0278 (7)	0.0178 (7)	0.0266 (8)	−0.0043 (6)	0.0187 (6)	−0.0013 (6)
C8	0.0375 (9)	0.0177 (7)	0.0359 (9)	−0.0010 (6)	0.0271 (8)	0.0024 (6)
C9	0.0162 (6)	0.0147 (6)	0.0138 (6)	−0.0016 (5)	0.0082 (5)	0.0012 (5)
C10	0.0187 (6)	0.0215 (7)	0.0192 (7)	−0.0013 (5)	0.0108 (6)	−0.0024 (5)
C11	0.0188 (7)	0.0267 (8)	0.0235 (7)	0.0011 (6)	0.0127 (6)	0.0033 (6)
C12	0.0172 (6)	0.0288 (8)	0.0204 (7)	−0.0038 (6)	0.0070 (6)	0.0061 (6)
C13	0.0250 (7)	0.0234 (7)	0.0172 (7)	−0.0081 (6)	0.0074 (6)	−0.0018 (6)
C14	0.0236 (7)	0.0165 (6)	0.0170 (7)	−0.0024 (5)	0.0107 (6)	−0.0003 (5)
C15	0.0155 (6)	0.0165 (6)	0.0137 (6)	−0.0023 (5)	0.0091 (5)	0.0004 (5)
C16	0.0179 (6)	0.0190 (7)	0.0194 (7)	−0.0011 (5)	0.0103 (5)	0.0029 (5)
C17	0.0214 (7)	0.0273 (8)	0.0189 (7)	−0.0022 (6)	0.0093 (6)	0.0081 (6)
C18	0.0236 (7)	0.0352 (9)	0.0140 (7)	−0.0090 (6)	0.0110 (6)	0.0006 (6)
C19	0.0241 (7)	0.0269 (7)	0.0179 (7)	−0.0074 (6)	0.0145 (6)	−0.0060 (6)
C20	0.0197 (6)	0.0192 (6)	0.0157 (6)	−0.0024 (5)	0.0108 (5)	−0.0014 (5)
P1	0.01563 (15)	0.01136 (15)	0.01348 (16)	−0.00006 (11)	0.00938 (13)	−0.00031 (12)
Se1	0.02669 (9)	0.01456 (8)	0.02525 (9)	0.00329 (5)	0.01918 (7)	−0.00012 (5)

Geometric parameters (Å, º) top

C1—C2	1.3973 (19)	C11—C12	1.392 (2)
C1—C6	1.4005 (19)	C11—H11	0.95
C1—P1	1.8108 (14)	C12—C13	1.383 (2)
C2—C3	1.392 (2)	C12—H12	0.95
C2—H2	0.95	C13—C14	1.391 (2)
C3—C4	1.397 (2)	C13—H13	0.95
C3—H3	0.95	C14—H14	0.95
C4—C5	1.401 (2)	C15—C20	1.3959 (19)
C4—C7	1.4733 (19)	C15—C16	1.3981 (19)
C5—C6	1.3857 (19)	C15—P1	1.8198 (14)
C5—H5	0.95	C16—C17	1.396 (2)
C6—H6	0.95	C16—H16	0.95
C7—C8	1.322 (2)	C17—C18	1.388 (2)
C7—H7	0.95	C17—H17	0.95
C8—H8A	0.95	C18—C19	1.387 (2)
C8—H8B	0.95	C18—H18	0.95
C9—C14	1.396 (2)	C19—C20	1.394 (2)
C9—C10	1.399 (2)	C19—H19	0.95
C9—P1	1.8173 (14)	C20—H20	0.95
C10—C11	1.387 (2)	P1—Se1	2.1138 (4)
C10—H10	0.95

C2—C1—C6	119.29 (12)	C13—C12—C11	119.86 (14)
C2—C1—P1	122.45 (10)	C13—C12—H12	120.1
C6—C1—P1	118.13 (10)	C11—C12—H12	120.1
C3—C2—C1	120.20 (13)	C12—C13—C14	120.49 (14)
C3—C2—H2	119.9	C12—C13—H13	119.8
C1—C2—H2	119.9	C14—C13—H13	119.8
C2—C3—C4	120.95 (13)	C13—C14—C9	120.00 (14)
C2—C3—H3	119.5	C13—C14—H14	120
C4—C3—H3	119.5	C9—C14—H14	120
C3—C4—C5	118.28 (13)	C20—C15—C16	119.64 (13)
C3—C4—C7	123.00 (13)	C20—C15—P1	120.28 (10)
C5—C4—C7	118.72 (13)	C16—C15—P1	120.07 (11)
C6—C5—C4	121.30 (13)	C17—C16—C15	119.78 (14)
C6—C5—H5	119.4	C17—C16—H16	120.1
C4—C5—H5	119.4	C15—C16—H16	120.1
C5—C6—C1	119.98 (13)	C18—C17—C16	120.19 (14)
C5—C6—H6	120	C18—C17—H17	119.9
C1—C6—H6	120	C16—C17—H17	119.9
C8—C7—C4	126.41 (15)	C19—C18—C17	120.23 (14)
C8—C7—H7	116.8	C19—C18—H18	119.9
C4—C7—H7	116.8	C17—C18—H18	119.9
C7—C8—H8A	120	C18—C19—C20	119.99 (14)
C7—C8—H8B	120	C18—C19—H19	120
H8A—C8—H8B	120	C20—C19—H19	120
C14—C9—C10	119.27 (13)	C19—C20—C15	120.14 (14)
C14—C9—P1	119.62 (11)	C19—C20—H20	119.9
C10—C9—P1	121.08 (11)	C15—C20—H20	119.9
C11—C10—C9	120.29 (14)	C1—P1—C9	105.68 (6)
C11—C10—H10	119.9	C1—P1—C15	104.47 (6)
C9—C10—H10	119.9	C9—P1—C15	107.07 (6)
C10—C11—C12	120.08 (14)	C1—P1—Se1	113.17 (4)
C10—C11—H11	120	C9—P1—Se1	112.96 (5)
C12—C11—H11	120	C15—P1—Se1	112.82 (5)

C6—C1—C2—C3	0.1 (2)	C16—C17—C18—C19	0.4 (2)
P1—C1—C2—C3	175.86 (11)	C17—C18—C19—C20	0.1 (2)
C1—C2—C3—C4	−0.7 (2)	C18—C19—C20—C15	−1.0 (2)
C2—C3—C4—C5	0.9 (2)	C16—C15—C20—C19	1.5 (2)
C2—C3—C4—C7	−178.22 (14)	P1—C15—C20—C19	−178.21 (11)
C3—C4—C5—C6	−0.6 (2)	C2—C1—P1—C9	14.26 (13)
C7—C4—C5—C6	178.61 (13)	C6—C1—P1—C9	−169.95 (11)
C4—C5—C6—C1	0.0 (2)	C2—C1—P1—C15	127.04 (12)
C2—C1—C6—C5	0.2 (2)	C6—C1—P1—C15	−57.17 (12)
P1—C1—C6—C5	−175.69 (11)	C2—C1—P1—Se1	−109.86 (11)
C3—C4—C7—C8	−4.9 (2)	C6—C1—P1—Se1	65.93 (11)
C5—C4—C7—C8	175.95 (16)	C14—C9—P1—C1	−115.72 (12)
C14—C9—C10—C11	0.8 (2)	C10—C9—P1—C1	62.47 (13)
P1—C9—C10—C11	−177.41 (11)	C14—C9—P1—C15	133.33 (11)
C9—C10—C11—C12	−1.0 (2)	C10—C9—P1—C15	−48.48 (13)
C10—C11—C12—C13	0.0 (2)	C14—C9—P1—Se1	8.54 (13)
C11—C12—C13—C14	1.1 (2)	C10—C9—P1—Se1	−173.27 (10)
C12—C13—C14—C9	−1.3 (2)	C20—C15—P1—C1	−42.60 (12)
C10—C9—C14—C13	0.4 (2)	C16—C15—P1—C1	137.66 (11)
P1—C9—C14—C13	178.59 (11)	C20—C15—P1—C9	69.18 (12)
C20—C15—C16—C17	−1.0 (2)	C16—C15—P1—C9	−110.55 (11)
P1—C15—C16—C17	178.70 (11)	C20—C15—P1—Se1	−165.94 (10)
C15—C16—C17—C18	0.1 (2)	C16—C15—P1—Se1	14.33 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1ⁱ	0.95	2.62	3.383 (2)	137
C3—H3···Cg2ⁱⁱ	0.95	2.88	3.5889 (19)	133
C12—H12···Cg2ⁱⁱⁱ	0.95	2.85	3.614 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇PSe
M_r	367.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.5310 (7), 11.1477 (7), 17.2187 (9)
β (°)	124.562 (3)
V (Å³)	1664.66 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.35
Crystal size (mm)	0.3 × 0.25 × 0.13

Data collection
Diffractometer	Bruker APEX DUO 4K-CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.526, 0.737
No. of measured, independent and observed [I > 2σ(I)] reflections	20089, 4166, 3921
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.063, 1.03
No. of reflections	4166
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.37, −0.41

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1ⁱ	0.95	2.62	3.383 (2)	137
C3—H3···Cg2ⁱⁱ	0.95	2.88	3.5889 (19)	133
C12—H12···Cg2ⁱⁱⁱ	0.95	2.85	3.614 (2)	138

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

Acknowledgements

Research funds of the University of Johannesburg is gratefully acknowledged.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). SADABS, SAINT and XPREP. BrukerAXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bunten, K. A., Chen, L., Fernandez, A. L. & Poë, A. J. (2002). Coord. Chem. Rev. 233–234, 41–51. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. 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
Roodt, A., Otto, S. & Steyl, G. (2003). Coord. Chem. Rev. 245, 121–137. Web of Science CSD CrossRef CAS 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

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Volume 68| Part 9| September 2012| Page o2690

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