Tris[4-(methyl­sulfan­yl)phen­yl]arsine

Shawkataly, O. bin; Khan, I.A.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S160053681002876X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2116

https://doi.org/10.1107/S160053681002876X

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Tris[4-(methylsulfanyl)phenyl]arsine

Omar bin Shawkataly,^a ^*‡ Imthyaz Ahmed Khan,^a § Chin Sing Yeap ^b ¶ and Hoong-Kun Fun ^b ‡‡

^aChemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: omarsa@usm.my

(Received 17 July 2010; accepted 19 July 2010; online 24 July 2010)

In the title compound, C₂₁H₂₁AsS₃, the three benzene rings make dihedral angles of 88.41 (10), 87.75 (9) and 74.74 (10)° with each other. The methylsulfanyl groups are roughly coplanar with their attached benzene rings [C—S—C—C torsion angles = −7.6 (2), 11.2 (2) and 4.1 (2)°]. In the crystal, weak C—H⋯π interactions link the molecules.

Related literature

For related structures of trisarylarsines with osmium and ruthenium, see: Cullen et al. (1995 ); Shawkataly et al. (2009a ,b , 2010a ,b ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₁AsS₃
M_r = 444.48
Monoclinic, P 2₁ /c
a = 11.0839 (2) Å
b = 11.4556 (2) Å
c = 17.3247 (2) Å
β = 110.860 (1)°
V = 2055.58 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 100 K
0.35 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.545, T_max = 0.821
31130 measured reflections
7111 independent reflections
5098 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.097
S = 1.01
7111 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯Cg1ⁱ	0.96	2.55	3.441 (3)	155
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681002876X/hb5559sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002876X/hb5559Isup2.hkl

checkCIF report

Comment top

Trisarylarsines are used in the synthesis of osmium and ruthenium cluster derivatives (Cullen et al., 1995; Shawkataly et al., 2009a, b, 2010a, b).

The three benzene rings of the title compound (Fig. 1) make dihedral angles (C1–C6/C7–C12, C1–C6/C13–C18 and C7–C12/C13–C18) of 88.41 (10), 87.75 (9) and 74.74 (10)° with each other respectively. The methylsulfanyl groups are nearly coplanar with the attached benzene rings [torsion angles of C19–S1–C4–C3 = -7.6 (2), C20–S2–C10–C9 = 11.2 (2) and C21–S3–C16–C17 = 4.1 (2)°]. In the crystal structure, the molecules are stacked along a axis (Fig. 2). Weak intermolecular C—H···π interactions further stabilize the crystal structure (Table 1).

Related literature top

For related structures of trisarylarsines with osmium and ruthenium, see: Cullen et al. (1995); Shawkataly et al. (2009a,b, 2010a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The reactions were conducted under an atmosphere of high purity nitrogen using standard Schlenk techniques and tetrahydrofuran (THF) dried over sodium metal. Tris(4-(methylsulfanyl)phenyl)arsine was prepared from arsenic trichloride and 4-(methylsulfanyl)phenylmagnesium bromide in tetrahydrofuran. Colourless blocks of (I) were obtained by slow evaporation from a chloroform solution.

Structure description top

Trisarylarsines are used in the synthesis of osmium and ruthenium cluster derivatives (Cullen et al., 1995; Shawkataly et al., 2009a, b, 2010a, b).

For related structures of trisarylarsines with osmium and ruthenium, see: Cullen et al. (1995); Shawkataly et al. (2009a,b, 2010a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I), viewed down the a axis, showing the molecules are stacked along a axis.

Tris[4-(methylsulfanyl)phenyl]arsine top

Crystal data top

C₂₁H₂₁AsS₃	F(000) = 912
M_r = 444.48	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6720 reflections
a = 11.0839 (2) Å	θ = 2.7–31.0°
b = 11.4556 (2) Å	µ = 1.96 mm⁻¹
c = 17.3247 (2) Å	T = 100 K
β = 110.860 (1)°	Block, colourless
V = 2055.58 (6) Å³	0.35 × 0.13 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	7111 independent reflections
Radiation source: fine-focus sealed tube	5098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
φ and ω scans	θ_max = 32.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.545, T_max = 0.821	k = −11→17
31130 measured reflections	l = −25→25

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0486P)²] where P = (F_o² + 2F_c²)/3
7111 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₁H₂₁AsS₃	V = 2055.58 (6) Å³
M_r = 444.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0839 (2) Å	µ = 1.96 mm⁻¹
b = 11.4556 (2) Å	T = 100 K
c = 17.3247 (2) Å	0.35 × 0.13 × 0.11 mm
β = 110.860 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7111 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5098 reflections with I > 2σ(I)
T_min = 0.545, T_max = 0.821	R_int = 0.051
31130 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.01	Δρ_max = 0.86 e Å⁻³
7111 reflections	Δρ_min = −0.51 e Å⁻³
229 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
As1	0.851830 (19)	0.703422 (18)	0.496255 (12)	0.01802 (6)
S1	0.60863 (5)	1.03859 (5)	0.17158 (3)	0.03019 (13)
S2	0.83788 (6)	1.05708 (5)	0.78874 (3)	0.02996 (13)
S3	1.44348 (5)	0.76333 (6)	0.50798 (4)	0.03192 (14)
C1	0.78015 (19)	0.80668 (17)	0.40006 (12)	0.0183 (4)
C2	0.64685 (19)	0.81069 (18)	0.35944 (13)	0.0224 (4)
H2A	0.5944	0.7653	0.3790	0.027*
C3	0.59018 (19)	0.88051 (19)	0.29053 (12)	0.0234 (4)
H3A	0.5008	0.8824	0.2651	0.028*
C4	0.66768 (19)	0.94822 (18)	0.25918 (12)	0.0204 (4)
C5	0.80152 (19)	0.94533 (17)	0.29981 (11)	0.0192 (4)
H5A	0.8542	0.9905	0.2802	0.023*
C6	0.85652 (18)	0.87601 (17)	0.36893 (11)	0.0183 (4)
H6A	0.9458	0.8754	0.3952	0.022*
C7	0.84768 (18)	0.81425 (17)	0.58127 (12)	0.0178 (4)
C8	0.8544 (2)	0.77177 (19)	0.65816 (13)	0.0262 (5)
H8A	0.8605	0.6918	0.6680	0.031*
C9	0.8520 (2)	0.8473 (2)	0.71996 (13)	0.0286 (5)
H9A	0.8567	0.8174	0.7709	0.034*
C10	0.84255 (19)	0.96751 (18)	0.70672 (12)	0.0204 (4)
C11	0.83575 (18)	1.01047 (18)	0.63009 (12)	0.0197 (4)
H11A	0.8293	1.0904	0.6201	0.024*
C12	0.83859 (18)	0.93414 (17)	0.56862 (12)	0.0186 (4)
H12A	0.8343	0.9639	0.5178	0.022*
C13	1.03380 (18)	0.72022 (17)	0.50883 (12)	0.0178 (4)
C14	1.0843 (2)	0.64556 (18)	0.46419 (12)	0.0214 (4)
H14A	1.0332	0.5857	0.4330	0.026*
C15	1.2091 (2)	0.65933 (19)	0.46564 (12)	0.0230 (4)
H15A	1.2408	0.6092	0.4351	0.028*
C16	1.28772 (19)	0.74795 (19)	0.51259 (12)	0.0209 (4)
C17	1.24043 (19)	0.81979 (18)	0.56012 (12)	0.0198 (4)
H17A	1.2931	0.8768	0.5938	0.024*
C18	1.11392 (19)	0.80605 (17)	0.55710 (11)	0.0190 (4)
H18A	1.0825	0.8555	0.5881	0.023*
C19	0.4396 (2)	1.0054 (2)	0.12929 (14)	0.0353 (6)
H19A	0.4018	1.0427	0.0765	0.053*
H19B	0.3984	1.0333	0.1660	0.053*
H19C	0.4281	0.9225	0.1228	0.053*
C20	0.7909 (3)	1.1960 (2)	0.73922 (14)	0.0367 (6)
H20A	0.7705	1.2484	0.7761	0.055*
H20B	0.7164	1.1862	0.6899	0.055*
H20C	0.8606	1.2276	0.7252	0.055*
C21	1.5139 (2)	0.8774 (3)	0.58105 (19)	0.0518 (8)
H21A	1.5994	0.8937	0.5821	0.078*
H21B	1.5180	0.8531	0.6350	0.078*
H21C	1.4619	0.9465	0.5652	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
As1	0.01501 (10)	0.01771 (11)	0.02239 (10)	−0.00177 (8)	0.00793 (8)	−0.00007 (8)
S1	0.0216 (3)	0.0365 (3)	0.0284 (3)	−0.0021 (2)	0.0039 (2)	0.0102 (2)
S2	0.0388 (3)	0.0320 (3)	0.0207 (2)	0.0064 (3)	0.0126 (2)	−0.0011 (2)
S3	0.0181 (3)	0.0435 (4)	0.0390 (3)	0.0006 (2)	0.0161 (2)	−0.0026 (3)
C1	0.0159 (9)	0.0198 (10)	0.0199 (9)	−0.0017 (8)	0.0074 (7)	−0.0023 (7)
C2	0.0152 (9)	0.0263 (11)	0.0274 (10)	−0.0050 (8)	0.0096 (8)	0.0010 (8)
C3	0.0136 (9)	0.0296 (12)	0.0265 (10)	−0.0020 (8)	0.0065 (8)	0.0013 (9)
C4	0.0186 (10)	0.0214 (10)	0.0210 (9)	0.0002 (8)	0.0069 (8)	−0.0015 (8)
C5	0.0176 (9)	0.0208 (10)	0.0208 (9)	−0.0029 (8)	0.0088 (7)	−0.0033 (8)
C6	0.0135 (9)	0.0216 (10)	0.0210 (9)	−0.0027 (7)	0.0075 (7)	−0.0029 (8)
C7	0.0122 (9)	0.0209 (10)	0.0220 (9)	0.0005 (7)	0.0081 (7)	0.0017 (7)
C8	0.0351 (13)	0.0199 (11)	0.0282 (11)	0.0051 (9)	0.0168 (9)	0.0061 (8)
C9	0.0379 (13)	0.0277 (12)	0.0230 (10)	0.0047 (10)	0.0143 (9)	0.0071 (9)
C10	0.0164 (9)	0.0260 (11)	0.0199 (9)	0.0016 (8)	0.0077 (7)	0.0003 (8)
C11	0.0166 (9)	0.0191 (10)	0.0243 (9)	0.0007 (8)	0.0085 (8)	0.0010 (8)
C12	0.0175 (9)	0.0197 (10)	0.0210 (9)	−0.0007 (8)	0.0097 (7)	0.0037 (7)
C13	0.0145 (9)	0.0195 (10)	0.0196 (9)	−0.0002 (7)	0.0061 (7)	0.0016 (7)
C14	0.0210 (10)	0.0200 (10)	0.0232 (9)	0.0013 (8)	0.0078 (8)	−0.0015 (8)
C15	0.0215 (10)	0.0256 (11)	0.0239 (10)	0.0044 (9)	0.0106 (8)	−0.0015 (8)
C16	0.0156 (9)	0.0248 (11)	0.0238 (10)	0.0037 (8)	0.0087 (8)	0.0046 (8)
C17	0.0137 (9)	0.0239 (11)	0.0215 (9)	0.0006 (7)	0.0059 (7)	0.0019 (8)
C18	0.0169 (9)	0.0215 (10)	0.0194 (9)	0.0011 (8)	0.0076 (7)	0.0001 (7)
C19	0.0242 (12)	0.0306 (13)	0.0392 (13)	0.0000 (10)	−0.0033 (10)	0.0034 (10)
C20	0.0505 (16)	0.0318 (14)	0.0249 (11)	0.0106 (11)	0.0100 (11)	−0.0038 (9)
C21	0.0193 (12)	0.069 (2)	0.0692 (19)	−0.0159 (13)	0.0189 (12)	−0.0260 (16)

Geometric parameters (Å, º) top

As1—C7	1.9574 (19)	C9—H9A	0.9300
As1—C13	1.960 (2)	C10—C11	1.392 (3)
As1—C1	1.9660 (19)	C11—C12	1.387 (3)
S1—C4	1.760 (2)	C11—H11A	0.9300
S1—C19	1.793 (2)	C12—H12A	0.9300
S2—C10	1.768 (2)	C13—C18	1.388 (3)
S2—C20	1.795 (2)	C13—C14	1.397 (3)
S3—C16	1.765 (2)	C14—C15	1.384 (3)
S3—C21	1.793 (3)	C14—H14A	0.9300
C1—C2	1.393 (3)	C15—C16	1.395 (3)
C1—C6	1.401 (3)	C15—H15A	0.9300
C2—C3	1.388 (3)	C16—C17	1.392 (3)
C2—H2A	0.9300	C17—C18	1.393 (3)
C3—C4	1.402 (3)	C17—H17A	0.9300
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.398 (3)	C19—H19A	0.9600
C5—C6	1.384 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—H6A	0.9300	C20—H20A	0.9600
C7—C12	1.389 (3)	C20—H20B	0.9600
C7—C8	1.395 (3)	C20—H20C	0.9600
C8—C9	1.384 (3)	C21—H21A	0.9600
C8—H8A	0.9300	C21—H21B	0.9600
C9—C10	1.394 (3)	C21—H21C	0.9600

C7—As1—C13	98.73 (8)	C11—C12—C7	121.50 (18)
C7—As1—C1	97.87 (8)	C11—C12—H12A	119.2
C13—As1—C1	97.15 (8)	C7—C12—H12A	119.2
C4—S1—C19	103.97 (10)	C18—C13—C14	118.11 (18)
C10—S2—C20	102.53 (10)	C18—C13—As1	123.30 (15)
C16—S3—C21	103.15 (11)	C14—C13—As1	118.53 (15)
C2—C1—C6	117.67 (18)	C15—C14—C13	121.01 (19)
C2—C1—As1	118.95 (14)	C15—C14—H14A	119.5
C6—C1—As1	123.38 (14)	C13—C14—H14A	119.5
C3—C2—C1	121.84 (18)	C14—C15—C16	120.41 (19)
C3—C2—H2A	119.1	C14—C15—H15A	119.8
C1—C2—H2A	119.1	C16—C15—H15A	119.8
C2—C3—C4	120.00 (19)	C17—C16—C15	119.12 (18)
C2—C3—H3A	120.0	C17—C16—S3	123.24 (16)
C4—C3—H3A	120.0	C15—C16—S3	117.64 (16)
C5—C4—C3	118.59 (18)	C16—C17—C18	119.79 (19)
C5—C4—S1	116.77 (15)	C16—C17—H17A	120.1
C3—C4—S1	124.64 (15)	C18—C17—H17A	120.1
C6—C5—C4	120.71 (18)	C13—C18—C17	121.48 (19)
C6—C5—H5A	119.6	C13—C18—H18A	119.3
C4—C5—H5A	119.6	C17—C18—H18A	119.3
C5—C6—C1	121.18 (18)	S1—C19—H19A	109.5
C5—C6—H6A	119.4	S1—C19—H19B	109.5
C1—C6—H6A	119.4	H19A—C19—H19B	109.5
C12—C7—C8	118.15 (18)	S1—C19—H19C	109.5
C12—C7—As1	122.86 (14)	H19A—C19—H19C	109.5
C8—C7—As1	118.99 (15)	H19B—C19—H19C	109.5
C9—C8—C7	120.8 (2)	S2—C20—H20A	109.5
C9—C8—H8A	119.6	S2—C20—H20B	109.5
C7—C8—H8A	119.6	H20A—C20—H20B	109.5
C8—C9—C10	120.74 (19)	S2—C20—H20C	109.5
C8—C9—H9A	119.6	H20A—C20—H20C	109.5
C10—C9—H9A	119.6	H20B—C20—H20C	109.5
C11—C10—C9	118.78 (18)	S3—C21—H21A	109.5
C11—C10—S2	123.63 (16)	S3—C21—H21B	109.5
C9—C10—S2	117.58 (15)	H21A—C21—H21B	109.5
C12—C11—C10	120.06 (19)	S3—C21—H21C	109.5
C12—C11—H11A	120.0	H21A—C21—H21C	109.5
C10—C11—H11A	120.0	H21B—C21—H21C	109.5

C7—As1—C1—C2	−89.18 (16)	C8—C9—C10—S2	179.13 (18)
C13—As1—C1—C2	170.93 (16)	C20—S2—C10—C11	11.2 (2)
C7—As1—C1—C6	91.80 (17)	C20—S2—C10—C9	−167.94 (19)
C13—As1—C1—C6	−8.09 (17)	C9—C10—C11—C12	−0.1 (3)
C6—C1—C2—C3	−0.1 (3)	S2—C10—C11—C12	−179.27 (15)
As1—C1—C2—C3	−179.13 (16)	C10—C11—C12—C7	0.2 (3)
C1—C2—C3—C4	1.0 (3)	C8—C7—C12—C11	−0.2 (3)
C2—C3—C4—C5	−1.3 (3)	As1—C7—C12—C11	179.94 (14)
C2—C3—C4—S1	179.00 (16)	C7—As1—C13—C18	−9.49 (18)
C19—S1—C4—C5	172.71 (16)	C1—As1—C13—C18	89.65 (17)
C19—S1—C4—C3	−7.6 (2)	C7—As1—C13—C14	173.47 (16)
C3—C4—C5—C6	0.8 (3)	C1—As1—C13—C14	−87.39 (16)
S1—C4—C5—C6	−179.54 (15)	C18—C13—C14—C15	−2.3 (3)
C4—C5—C6—C1	0.2 (3)	As1—C13—C14—C15	174.91 (15)
C2—C1—C6—C5	−0.5 (3)	C13—C14—C15—C16	0.6 (3)
As1—C1—C6—C5	178.50 (14)	C14—C15—C16—C17	2.2 (3)
C13—As1—C7—C12	79.74 (17)	C14—C15—C16—S3	−177.57 (16)
C1—As1—C7—C12	−18.79 (18)	C21—S3—C16—C17	4.1 (2)
C13—As1—C7—C8	−100.12 (17)	C21—S3—C16—C15	−176.15 (18)
C1—As1—C7—C8	161.35 (16)	C15—C16—C17—C18	−3.1 (3)
C12—C7—C8—C9	0.0 (3)	S3—C16—C17—C18	176.61 (15)
As1—C7—C8—C9	179.87 (17)	C14—C13—C18—C17	1.3 (3)
C7—C8—C9—C10	0.1 (3)	As1—C13—C18—C17	−175.74 (14)
C8—C9—C10—C11	−0.1 (3)	C16—C17—C18—C13	1.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···Cg1ⁱ	0.96	2.55	3.441 (3)	155

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁AsS₃
M_r	444.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.0839 (2), 11.4556 (2), 17.3247 (2)
β (°)	110.860 (1)
V (Å³)	2055.58 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.96
Crystal size (mm)	0.35 × 0.13 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.545, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	31130, 7111, 5098
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.746

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.097, 1.01
No. of reflections	7111
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.51

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···Cg1ⁱ	0.96	2.55	3.441 (3)	155

Symmetry code: (i) x+1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: B-6034-2009. On secondment to: Multimedia University, Melaka Campus, Jalan Ayer Keroh Lama, 74750 Melaka, Malaysia.

§Thomson Reuters ResearcherID: E-2833-2010.

¶Thomson Reuters ResearcherID: A-5523-2009.

‡‡Thomson Reuters ResearcherID: A-3561-2009. Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research grant No. 1001/PJJAUH/811115. IAK is grateful to USM for a Visiting Researcher position. HKF and CSY thank USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY also thanks USM for the award of a USM Fellowship.

References

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