2-(4-Iodo­phen­yl)-5-methyl-3-methyl­sulfinyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536808013706

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1061

doi:10.1107/S1600536808013706

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2-(4-Iodophenyl)-5-methyl-3-methylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 6 May 2008; accepted 8 May 2008; online 10 May 2008)

The title compound, C₁₆H₁₃IO₂S, was prepared by the oxidation of 2-(4-iodophenyl)-5-methyl-3-methylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The 4-iodophenyl ring makes a dihedral angle of 37.97 (9)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of this plane. The molecular packing is stabilized by C—H⋯π interactions between H atoms on the 4-iodophenyl ring and the benzofuran rings, and by an I⋯O halogen bond of 3.252 (2) Å with a nearly linear C—I⋯O angle of 163.06 (8)°. In addition, the stacked molecules exhibit inversion-related S⋯O contacts [3.209 (2) Å] involving the sulfinyl groups.

Related literature

For the crystal structures of similar 2-aryl-5-methyl-3-methylsulfinyl-1-benzofuran compounds, see: Choi et al. (2007a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2007c ). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998 ).

Experimental

Crystal data

C₁₆H₁₃IO₂S
M_r = 396.22
Monoclinic, P 2₁ /n
a = 9.258 (2) Å
b = 15.939 (3) Å
c = 10.299 (2) Å
β = 103.471 (3)°
V = 1477.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.31 mm⁻¹
T = 173 (2) K
0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.443, T_max = 0.508
8743 measured reflections
3227 independent reflections
2934 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.065
S = 1.15
3227 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg1ⁱ	0.95	3.01	3.617 (4)	125
C11—H11⋯Cg2ⁱ	0.95	2.77	3.643 (4)	148
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the O1/C8/C1/C2/C7 furan ring, respectively.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013706/sj2496sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013706/sj2496Isup2.hkl

checkCIF report

Comment top

This work is related to our preceding communications on the synthesis and structure of 2-aryl-5-methyl-3-methylsulfinyl-1-benzofuran derivatives, viz. 2-(4-bromophenyl)-5-methyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2-(4-bromophenyl)-5,7-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007b). Here we report the crystal structure of the title compound, 2-(4-iodophenyl)-5-methyl-3-methylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.008Å from the least-squares plane defined by the nine constituent atoms. The 4-iodophenyl ring (C9—C14) makes a dihedral angle of 37.97 (9)° with the plane of the benzofuran fragment. The molecular packing (Fig. 2) is stabilized by two different C—H···π interactions within each stack of molecules; one between a 4-iodophenyl H atom and the benzene ring (Cg1ⁱ), with a C10—H10···Cg1ⁱ separation of 3.617 (4) Å, and a second between a 4-iodophenyl H atom and the furan ring (Cg2ⁱ), with a C11—H11···Cg2ⁱ separation of 3.643 (4) Å, (Fig. 2 and Table 1; Cg1 and Cg2 are the centroids of the C2—C7 benzene ring and the O1/C8/C1/C2/C7 furan ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by an I···O halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen of a neighbouring S═O unit, with a I···O2ⁱⁱ distance of 3.252 (2) Å (symmetry code as Fig. 2). In addition, the crystal packing exhibits a sulfinyl-sulfinyl interaction (Choi et al., 2007c) interpreted as similar to a type-II carbonyl-carbonyl interaction (Allen et al., 1998), with S···O2ⁱⁱⁱ and O2···Sⁱⁱⁱ distance of 3.209 (2)Å (symmetry code as in Fig. 2)

Related literature top

For the crystal structures of similar 2-aryl-5-methyl-3-methylsulfinyl-1-benzofuran compounds, see: Choi et al. (2007a,b). For a review of halogen bonding, see: Politzer et al. (2007). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2007c). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998). Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the O1/C8/C1/C2/C7 furan ring, respectively

Experimental top

3-Chloroperoxybenzoic acid (77%, 247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-(4-iodophenyl)-5-methyl-3-methylsulanyl-1-benzofuran (380 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After stirring at room temperature for 2 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (ethyl acetate) to afford the title compound as a colorless solid [yield 84%, m.p. 472–473 K; R_f = 0.61 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of title compound in tetrahydrofuran at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.48 (s, 3H), 3.11 (s, 3H), 7.22 (d, J = 8.04 Hz, 1H), 7.42 (d, J = 8.44 Hz, 1H), 7.75 (d, J = 6.96 Hz, 2H), 7.85 (d, J = 6.96 Hz, 2H), 7.99 (s, 1H); EI—MS 396 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. C—H···π, I···O halogen bond and S···O interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (i) x - 1/2, -y + 3/2, z - 1/2; (ii) x + 1/2, y, z - 1; (iii) -x + 1, -y + 1, -z + 1; (iv) x + 1, y, z + 1; (v) x + 1/2, -y + 3/2, z + 1/2.]

2-(4-Iodophenyl)-5-methyl-3-methylsulfinyl-1-benzofuran top

Crystal data top

C₁₆H₁₃IO₂S	F(000) = 776
M_r = 396.22	D_x = 1.781 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 472–473 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.258 (2) Å	Cell parameters from 6653 reflections
b = 15.939 (3) Å	θ = 2.4–28.2°
c = 10.299 (2) Å	µ = 2.31 mm⁻¹
β = 103.471 (3)°	T = 173 K
V = 1477.9 (5) Å³	Block, colorless
Z = 4	0.40 × 0.30 × 0.30 mm

Data collection top

Bruker SMART CCD diffractometer	3227 independent reflections
Radiation source: fine-focus sealed tube	2934 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.4°
ϕ and ω scans	h = −11→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −20→20
T_min = 0.443, T_max = 0.508	l = −11→13
8743 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0226P)² + 1.1637P] where P = (F_o² + 2F_c²)/3
3227 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.94 e Å⁻³

Crystal data top

C₁₆H₁₃IO₂S	V = 1477.9 (5) Å³
M_r = 396.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.258 (2) Å	µ = 2.31 mm⁻¹
b = 15.939 (3) Å	T = 173 K
c = 10.299 (2) Å	0.40 × 0.30 × 0.30 mm
β = 103.471 (3)°

Data collection top

Bruker SMART CCD diffractometer	3227 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2934 reflections with I > 2σ(I)
T_min = 0.443, T_max = 0.508	R_int = 0.030
8743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.15	Δρ_max = 0.54 e Å⁻³
3227 reflections	Δρ_min = −0.94 e Å⁻³
183 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
I	−0.134684 (19)	0.613119 (11)	−0.281817 (17)	0.03372 (7)
S	0.51165 (7)	0.54138 (4)	0.32703 (6)	0.02482 (13)
O1	0.61196 (19)	0.66982 (11)	0.02820 (17)	0.0251 (4)
O2	0.5977 (2)	0.57384 (14)	0.45895 (18)	0.0389 (5)
C1	0.5913 (3)	0.59181 (15)	0.2070 (2)	0.0220 (5)
C2	0.7456 (3)	0.61452 (15)	0.2246 (2)	0.0231 (5)
C3	0.8760 (3)	0.60093 (15)	0.3218 (3)	0.0262 (5)
H3	0.8746	0.5687	0.3991	0.031*
C4	1.0087 (3)	0.63528 (17)	0.3040 (3)	0.0309 (6)
C5	1.0091 (3)	0.68158 (17)	0.1884 (3)	0.0329 (6)
H5	1.1006	0.7038	0.1771	0.039*
C6	0.8810 (3)	0.69632 (16)	0.0895 (3)	0.0308 (6)
H6	0.8824	0.7277	0.0114	0.037*
C7	0.7515 (3)	0.66243 (15)	0.1120 (2)	0.0249 (5)
C8	0.5155 (3)	0.62626 (14)	0.0892 (2)	0.0228 (5)
C9	0.3610 (3)	0.62508 (15)	0.0136 (2)	0.0217 (5)
C10	0.3001 (3)	0.69536 (16)	−0.0607 (3)	0.0270 (5)
H10	0.3572	0.7453	−0.0564	0.032*
C11	0.1575 (3)	0.69273 (16)	−0.1403 (3)	0.0284 (5)
H11	0.1162	0.7410	−0.1893	0.034*
C12	0.0746 (3)	0.61946 (15)	−0.1483 (2)	0.0235 (5)
C13	0.1323 (3)	0.54923 (15)	−0.0743 (2)	0.0230 (5)
H13	0.0746	0.4995	−0.0797	0.028*
C14	0.2744 (3)	0.55201 (15)	0.0075 (2)	0.0218 (5)
H14	0.3134	0.5044	0.0595	0.026*
C15	1.1498 (3)	0.62338 (19)	0.4100 (3)	0.0417 (7)
H15A	1.1345	0.6425	0.4962	0.063*
H15B	1.2298	0.6561	0.3867	0.063*
H15C	1.1769	0.5638	0.4160	0.063*
C16	0.5769 (3)	0.43689 (17)	0.3073 (3)	0.0317 (6)
H16A	0.6833	0.4386	0.3096	0.048*
H16B	0.5227	0.4139	0.2216	0.048*
H16C	0.5604	0.4013	0.3801	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.02443 (11)	0.04004 (12)	0.03256 (11)	−0.00188 (7)	−0.00175 (7)	0.00229 (7)
S	0.0250 (3)	0.0303 (3)	0.0206 (3)	−0.0021 (2)	0.0083 (2)	−0.0031 (2)
O1	0.0205 (8)	0.0272 (9)	0.0277 (9)	−0.0025 (7)	0.0057 (7)	0.0030 (7)
O2	0.0418 (12)	0.0538 (13)	0.0214 (9)	−0.0143 (10)	0.0082 (8)	−0.0077 (9)
C1	0.0224 (12)	0.0229 (11)	0.0215 (11)	−0.0001 (9)	0.0066 (9)	−0.0038 (9)
C2	0.0239 (13)	0.0225 (11)	0.0233 (11)	0.0009 (9)	0.0062 (10)	−0.0069 (9)
C3	0.0251 (13)	0.0251 (12)	0.0274 (12)	0.0031 (9)	0.0039 (10)	−0.0077 (9)
C4	0.0231 (13)	0.0290 (13)	0.0382 (14)	0.0037 (10)	0.0024 (11)	−0.0142 (11)
C5	0.0209 (13)	0.0293 (13)	0.0497 (16)	−0.0028 (10)	0.0108 (11)	−0.0095 (12)
C6	0.0257 (13)	0.0281 (13)	0.0413 (15)	−0.0005 (10)	0.0133 (11)	−0.0007 (11)
C7	0.0212 (12)	0.0227 (12)	0.0313 (12)	−0.0002 (9)	0.0067 (10)	−0.0042 (10)
C8	0.0217 (12)	0.0216 (11)	0.0259 (12)	−0.0013 (9)	0.0076 (10)	−0.0025 (9)
C9	0.0208 (12)	0.0245 (12)	0.0203 (11)	−0.0006 (9)	0.0055 (9)	−0.0019 (9)
C10	0.0252 (13)	0.0236 (12)	0.0319 (13)	−0.0040 (10)	0.0062 (10)	0.0030 (10)
C11	0.0286 (13)	0.0250 (12)	0.0308 (13)	0.0012 (10)	0.0051 (11)	0.0068 (10)
C12	0.0190 (11)	0.0295 (13)	0.0221 (11)	0.0002 (9)	0.0046 (9)	−0.0014 (9)
C13	0.0252 (12)	0.0211 (11)	0.0245 (11)	−0.0034 (9)	0.0095 (10)	−0.0024 (9)
C14	0.0247 (12)	0.0209 (11)	0.0202 (11)	0.0007 (9)	0.0062 (9)	0.0014 (9)
C15	0.0240 (14)	0.0445 (17)	0.0514 (18)	0.0020 (12)	−0.0017 (13)	−0.0162 (14)
C16	0.0351 (15)	0.0325 (14)	0.0296 (13)	0.0038 (11)	0.0116 (11)	0.0046 (11)

Geometric parameters (Å, º) top

I—O2ⁱ	3.252 (2)	C6—H6	0.9500
I—C12	2.101 (3)	C8—C9	1.461 (3)
S—O2	1.4981 (19)	C9—C10	1.399 (3)
S—O2ⁱⁱ	3.209 (2)	C9—C14	1.407 (3)
S—C1	1.773 (2)	C10—C11	1.383 (4)
S—C16	1.799 (3)	C10—H10	0.9500
O1—C7	1.381 (3)	C11—C12	1.389 (3)
O1—C8	1.391 (3)	C11—H11	0.9500
C1—C8	1.367 (3)	C12—C13	1.389 (3)
C1—C2	1.444 (3)	C13—C14	1.388 (3)
C2—C3	1.394 (4)	C13—H13	0.9500
C2—C7	1.400 (3)	C14—H14	0.9500
C3—C4	1.395 (4)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.402 (4)	C15—H15C	0.9800
C4—C15	1.507 (4)	C16—H16A	0.9800
C5—C6	1.391 (4)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.383 (4)

C12—I—O2ⁱ	163.06 (8)	C10—C9—C8	120.1 (2)
O2—S—C1	104.84 (12)	C14—C9—C8	120.7 (2)
O2—S—C16	107.47 (13)	C11—C10—C9	120.5 (2)
C1—S—C16	97.80 (12)	C11—C10—H10	119.8
C7—O1—C8	106.30 (18)	C9—C10—H10	119.8
C8—C1—C2	107.4 (2)	C10—C11—C12	119.9 (2)
C8—C1—S	126.1 (2)	C10—C11—H11	120.1
C2—C1—S	125.89 (18)	C12—C11—H11	120.1
C3—C2—C7	119.1 (2)	C13—C12—C11	120.6 (2)
C3—C2—C1	135.8 (2)	C13—C12—I	119.88 (18)
C7—C2—C1	105.1 (2)	C11—C12—I	119.44 (18)
C2—C3—C4	119.1 (2)	C14—C13—C12	119.7 (2)
C2—C3—H3	120.5	C14—C13—H13	120.1
C4—C3—H3	120.5	C12—C13—H13	120.1
C3—C4—C5	119.7 (2)	C13—C14—C9	120.2 (2)
C3—C4—C15	119.8 (3)	C13—C14—H14	119.9
C5—C4—C15	120.6 (3)	C9—C14—H14	119.9
C6—C5—C4	122.7 (2)	C4—C15—H15A	109.5
C6—C5—H5	118.7	C4—C15—H15B	109.5
C4—C5—H5	118.7	H15A—C15—H15B	109.5
C7—C6—C5	115.9 (3)	C4—C15—H15C	109.5
C7—C6—H6	122.1	H15A—C15—H15C	109.5
C5—C6—H6	122.1	H15B—C15—H15C	109.5
O1—C7—C6	125.7 (2)	S—C16—H16A	109.5
O1—C7—C2	110.7 (2)	S—C16—H16B	109.5
C6—C7—C2	123.6 (2)	H16A—C16—H16B	109.5
C1—C8—O1	110.5 (2)	S—C16—H16C	109.5
C1—C8—C9	134.8 (2)	H16A—C16—H16C	109.5
O1—C8—C9	114.6 (2)	H16B—C16—H16C	109.5
C10—C9—C14	119.1 (2)

O2—S—C1—C8	−136.9 (2)	C1—C2—C7—C6	−179.6 (2)
C16—S—C1—C8	112.7 (2)	C2—C1—C8—O1	0.4 (3)
O2—S—C1—C2	33.6 (2)	S—C1—C8—O1	172.33 (17)
C16—S—C1—C2	−76.9 (2)	C2—C1—C8—C9	178.0 (3)
C8—C1—C2—C3	178.7 (3)	S—C1—C8—C9	−10.1 (4)
S—C1—C2—C3	6.8 (4)	C7—O1—C8—C1	−0.5 (3)
C8—C1—C2—C7	−0.2 (3)	C7—O1—C8—C9	−178.63 (19)
S—C1—C2—C7	−172.09 (18)	C1—C8—C9—C10	146.5 (3)
C7—C2—C3—C4	−0.1 (3)	O1—C8—C9—C10	−36.0 (3)
C1—C2—C3—C4	−178.9 (3)	C1—C8—C9—C14	−37.5 (4)
C2—C3—C4—C5	−0.9 (4)	O1—C8—C9—C14	140.0 (2)
C2—C3—C4—C15	178.2 (2)	C14—C9—C10—C11	−0.8 (4)
C3—C4—C5—C6	1.0 (4)	C8—C9—C10—C11	175.3 (2)
C15—C4—C5—C6	−178.1 (2)	C9—C10—C11—C12	−1.0 (4)
C4—C5—C6—C7	0.1 (4)	C10—C11—C12—C13	1.7 (4)
C8—O1—C7—C6	179.8 (2)	C10—C11—C12—I	−174.85 (19)
C8—O1—C7—C2	0.4 (2)	C11—C12—C13—C14	−0.6 (4)
C5—C6—C7—O1	179.4 (2)	I—C12—C13—C14	175.94 (17)
C5—C6—C7—C2	−1.2 (4)	C12—C13—C14—C9	−1.2 (3)
C3—C2—C7—O1	−179.3 (2)	C10—C9—C14—C13	1.9 (3)
C1—C2—C7—O1	−0.2 (3)	C8—C9—C14—C13	−174.2 (2)
C3—C2—C7—C6	1.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱⁱⁱ	0.95	3.01	3.617 (4)	125
C11—H11···Cg2ⁱⁱⁱ	0.95	2.77	3.643 (4)	148

Symmetry code: (iii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃IO₂S
M_r	396.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.258 (2), 15.939 (3), 10.299 (2)
β (°)	103.471 (3)
V (Å³)	1477.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.31
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.443, 0.508
No. of measured, independent and observed [I > 2σ(I)] reflections	8743, 3227, 2934
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.065, 1.15
No. of reflections	3227
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.94

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.95	3.01	3.617 (4)	125.0
C11—H11···Cg2ⁱ	0.95	2.77	3.643 (4)	148.4

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (1998). DIAMOND, Crystal Impact GbR. Bonn, Germany. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3295. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o4282. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007c). Acta Cryst. E63, o4811. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Page o1061

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