5-Iodo-2,7-dimethyl-3-phenyl­sulfonyl-1-benzofuran

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

doi:10.1107/S1600536808011240

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o930

doi:10.1107/S1600536808011240

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5-Iodo-2,7-dimethyl-3-phenylsulfonyl-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 18 April 2008; accepted 20 April 2008; online 30 April 2008)

The title compound, C₁₆H₁₃IO₃S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π–π interactions between the furan and benzene rings of neighbouring molecules, and between the benzene rings of neighbouring molecules; the centroid–centroid distances within the stack are 3.700 (4) and 3.788 (4) Å. In addition, the crystal structure exhibits inter- and intramolecular C—H⋯O interactions, and an I⋯O halogen bond with an I⋯O distance of 3.282 (2) Å and a nearly linear C—I⋯O angle of 165.69 (8)°.

Related literature

For the crystal structures of similar 3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₃IO₃S
M_r = 412.22
Monoclinic, P 2₁ /n
a = 8.1165 (5) Å
b = 14.0295 (9) Å
c = 13.2470 (8) Å
β = 90.320 (1)°
V = 1508.42 (16) Å³
Z = 4
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 173 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.579, T_max = 0.641
9110 measured reflections
3285 independent reflections
3069 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.074
S = 0.99
3285 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 1.13 e Å⁻³
Δρ_min = −1.01 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.95	2.59	3.382 (4)	141
C13—H13⋯O3ⁱⁱ	0.95	2.44	3.342 (4)	159
C14—H14⋯O2	0.95	2.58	2.931 (4)	103
C16—H16B⋯O3	0.98	2.48	3.191 (4)	129
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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 global, I. DOI: 10.1107/S1600536808011240/zl2112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011240/zl2112Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing studies on the synthesis and structure of 3-phenyl-sulfonyl-1-benzofuran analogues, the crystal structure of 5-bromo-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008a) and 2,5,7-trimethyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008b) have been recently described in the literature. Herein we report the molecular and crystal structure of the title ompound, 5-iodo-2,7-dimethyl-3-phenylsulfonyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.009 Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9—C14) makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by two different π—π interactions within each stack of molecules; one between the furan ring (Cg1) and an adjacent benzene ring (Cg2^v) of a benzofuran unit {distance 3.700 (4) Å}, and a second between the benzene ring (Cg2) and an adjacent benzene ring (Cg2ⁱⁱⁱ) of the benzofuran unit {distance 3.788 (4) Å}(Cg1 and Cg2 are the centroids of the O1/C8/C1/C2/C7 furan ring and the C2—C7 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by inter- and intramolecular C—H···O interactions (Table 1), and by a halogen bond (Politzer et al., 2007) between the iodine atom and the oxygen atom of the S═O unit (Fig. 2; symmetry code as in Fig, 2).

Related literature top

For the crystal structures of similar 3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (471 mg, 2.1 mmol) was added in small portions to a stirred solution of 5-iodo-2,7-dimethyl 3-phenylsulfanyl-1-benzofuran (380 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, 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 (hexane-ethyl acetate, 2: 1 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 431–432 K; R_f = 0.61 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.41 (s, 3H), 2.80 (s, 3H), 7.42 (s, 1H), 7.50–7.32 (m, 3H), 7.98 (d, J = 7.32 Hz, 2H), 8.06 (s, 1H); EI—MS 412 [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. π—π interactions, C—H···O hydrogen bonds, and I···O halogen bond (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, y, z; (iii) -x, -y + 1, -z + 1; (iv) x - 1/2, -y + 1/2, z - 1/2; (v) -x + 1, -y + 1, -z + 1; (vi) x + 1/2, -y + 3/2, z - 1/2; (vii) x + 1/2, -y + 1/2, z + 1/2; (viii) x + 1, y, z.]

5-Iodo-2,7-dimethyl-3-phenylsulfonyl-1-benzofuran top

Crystal data top

C₁₆H₁₃IO₃S	F(000) = 808
M_r = 412.22	D_x = 1.815 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 431–432 K
Hall symbol: -P_2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.1165 (5) Å	Cell parameters from 6912 reflections
b = 14.0295 (9) Å	θ = 2.9–28.3°
c = 13.2470 (8) Å	µ = 2.27 mm⁻¹
β = 90.320 (1)°	T = 173 K
V = 1508.42 (16) Å³	Block, colorless
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	3285 independent reflections
Radiation source: fine-focus sealed tube	3069 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.9°
ϕ and ω scans	h = −10→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −17→16
T_min = 0.579, T_max = 0.641	l = −16→16
9110 measured reflections

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)] = 0.027	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0428P)² + 1.8205P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
3285 reflections	Δρ_max = 1.13 e Å⁻³
193 parameters	Δρ_min = −1.02 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0204 (8)

Crystal data top

C₁₆H₁₃IO₃S	V = 1508.42 (16) Å³
M_r = 412.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.1165 (5) Å	µ = 2.27 mm⁻¹
b = 14.0295 (9) Å	T = 173 K
c = 13.2470 (8) Å	0.40 × 0.20 × 0.20 mm
β = 90.320 (1)°

Data collection top

Bruker SMART CCD diffractometer	3285 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	3069 reflections with I > 2σ(I)
T_min = 0.579, T_max = 0.641	R_int = 0.032
9110 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 0.99	Δρ_max = 1.13 e Å⁻³
3285 reflections	Δρ_min = −1.02 e Å⁻³
193 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	0.01644 (2)	0.271298 (12)	0.412327 (13)	0.03036 (10)
S	0.31859 (7)	0.47908 (4)	0.80435 (4)	0.02106 (14)
O1	0.3994 (2)	0.62669 (12)	0.55765 (13)	0.0216 (3)
O2	0.2767 (3)	0.38039 (13)	0.79316 (14)	0.0304 (4)
O3	0.4628 (2)	0.50442 (16)	0.86163 (15)	0.0343 (4)
C1	0.3367 (3)	0.52624 (17)	0.68298 (18)	0.0196 (5)
C2	0.2699 (3)	0.48622 (17)	0.59100 (18)	0.0192 (5)
C3	0.1833 (3)	0.40340 (17)	0.56413 (18)	0.0216 (5)
H3	0.1530	0.3570	0.6128	0.026*
C4	0.1444 (3)	0.39292 (18)	0.46308 (19)	0.0236 (5)
C5	0.1860 (3)	0.46045 (18)	0.39014 (19)	0.0240 (5)
H5	0.1549	0.4497	0.3218	0.029*
C6	0.2718 (3)	0.54330 (18)	0.41501 (18)	0.0224 (5)
C7	0.3120 (3)	0.55133 (17)	0.51657 (18)	0.0204 (5)
C8	0.4119 (3)	0.60993 (18)	0.65900 (18)	0.0216 (5)
C9	0.1490 (3)	0.53904 (18)	0.85741 (18)	0.0240 (5)
C10	0.1754 (4)	0.6275 (2)	0.9019 (2)	0.0381 (7)
H10	0.2825	0.6548	0.9033	0.046*
C11	0.0447 (5)	0.6749 (3)	0.9437 (3)	0.0508 (9)
H11	0.0610	0.7355	0.9741	0.061*
C12	−0.1097 (5)	0.6348 (3)	0.9418 (2)	0.0497 (10)
H12	−0.1996	0.6682	0.9707	0.060*
C13	−0.1359 (4)	0.5464 (3)	0.8984 (2)	0.0456 (9)
H13	−0.2432	0.5193	0.8978	0.055*
C14	−0.0047 (3)	0.4970 (2)	0.85537 (19)	0.0311 (6)
H14	−0.0207	0.4361	0.8255	0.037*
C15	0.3140 (4)	0.6191 (2)	0.3392 (2)	0.0308 (6)
H15A	0.2394	0.6735	0.3474	0.046*
H15B	0.3021	0.5933	0.2708	0.046*
H15C	0.4279	0.6401	0.3500	0.046*
C16	0.4982 (3)	0.6852 (2)	0.7172 (2)	0.0284 (5)
H16A	0.6032	0.7001	0.6846	0.043*
H16B	0.5189	0.6626	0.7861	0.043*
H16C	0.4295	0.7426	0.7193	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.02777 (13)	0.02830 (13)	0.03502 (14)	−0.00635 (6)	0.00123 (8)	−0.00964 (7)
S	0.0220 (3)	0.0220 (3)	0.0192 (3)	0.0029 (2)	0.0004 (2)	0.0016 (2)
O1	0.0229 (8)	0.0197 (8)	0.0224 (8)	−0.0016 (7)	0.0032 (7)	0.0006 (7)
O2	0.0432 (12)	0.0204 (9)	0.0275 (9)	0.0044 (8)	0.0045 (8)	0.0035 (7)
O3	0.0264 (10)	0.0488 (12)	0.0277 (9)	−0.0001 (9)	−0.0064 (8)	0.0021 (9)
C1	0.0192 (11)	0.0205 (11)	0.0190 (11)	0.0006 (9)	0.0015 (9)	−0.0001 (9)
C2	0.0169 (10)	0.0208 (11)	0.0200 (11)	0.0020 (9)	0.0024 (8)	−0.0003 (9)
C3	0.0208 (11)	0.0198 (11)	0.0243 (11)	−0.0006 (9)	0.0030 (9)	−0.0005 (9)
C4	0.0196 (11)	0.0228 (12)	0.0285 (12)	0.0002 (9)	0.0019 (9)	−0.0051 (10)
C5	0.0243 (12)	0.0274 (12)	0.0203 (11)	0.0035 (10)	−0.0015 (9)	−0.0028 (10)
C6	0.0222 (12)	0.0232 (12)	0.0219 (11)	0.0054 (9)	0.0025 (9)	0.0018 (10)
C7	0.0178 (11)	0.0185 (11)	0.0250 (11)	0.0004 (8)	0.0027 (9)	−0.0012 (9)
C8	0.0212 (11)	0.0213 (11)	0.0222 (11)	0.0010 (9)	0.0028 (9)	−0.0005 (9)
C9	0.0296 (13)	0.0250 (12)	0.0174 (10)	0.0053 (10)	0.0046 (10)	0.0042 (9)
C10	0.0479 (18)	0.0284 (14)	0.0383 (15)	−0.0016 (13)	0.0175 (14)	−0.0031 (12)
C11	0.073 (3)	0.0323 (16)	0.0474 (19)	0.0140 (16)	0.0297 (18)	0.0001 (14)
C12	0.058 (2)	0.059 (2)	0.0323 (16)	0.0347 (18)	0.0188 (15)	0.0125 (15)
C13	0.0245 (14)	0.085 (3)	0.0269 (14)	0.0115 (15)	0.0020 (11)	0.0152 (16)
C14	0.0261 (13)	0.0458 (16)	0.0214 (12)	0.0018 (12)	−0.0038 (10)	0.0030 (11)
C15	0.0378 (15)	0.0302 (14)	0.0245 (12)	0.0014 (11)	0.0019 (11)	0.0068 (11)
C16	0.0288 (13)	0.0264 (13)	0.0299 (13)	−0.0052 (11)	0.0018 (10)	−0.0049 (11)

Geometric parameters (Å, º) top

I—O2ⁱ	3.282 (2)	C8—C16	1.481 (3)
I—C4	2.106 (3)	C9—C14	1.380 (4)
S—O2	1.433 (2)	C9—C10	1.390 (4)
S—O3	1.436 (2)	C10—C11	1.371 (4)
S—C1	1.746 (2)	C10—H10	0.9500
S—C9	1.762 (3)	C11—C12	1.374 (6)
O1—C8	1.366 (3)	C11—H11	0.9500
O1—C7	1.383 (3)	C12—C13	1.383 (6)
C1—C8	1.362 (3)	C12—H12	0.9500
C1—C2	1.444 (3)	C13—C14	1.395 (4)
C2—C7	1.388 (3)	C13—H13	0.9500
C2—C3	1.403 (3)	C14—H14	0.9500
C3—C4	1.381 (3)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.396 (4)	C15—H15C	0.9800
C5—C6	1.394 (4)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.387 (3)	C16—H16C	0.9800
C6—C15	1.504 (3)

C4—I—O2ⁱ	165.69 (8)	O1—C8—C16	114.9 (2)
O2—S—O3	119.1 (1)	C14—C9—C10	121.8 (3)
O2—S—C1	107.0 (1)	C14—C9—S	119.7 (2)
O3—S—C1	108.7 (1)	C10—C9—S	118.5 (2)
O2—S—C9	108.5 (1)	C11—C10—C9	119.1 (3)
O3—S—C9	107.9 (1)	C11—C10—H10	120.4
C1—S—C9	104.9 (1)	C9—C10—H10	120.4
C8—O1—C7	106.9 (2)	C10—C11—C12	120.1 (3)
C8—C1—C2	107.7 (2)	C10—C11—H11	120.0
C8—C1—S	125.6 (2)	C12—C11—H11	120.0
C2—C1—S	126.6 (2)	C11—C12—C13	120.9 (3)
C7—C2—C3	119.3 (2)	C11—C12—H12	119.6
C7—C2—C1	104.5 (2)	C13—C12—H12	119.6
C3—C2—C1	136.1 (2)	C12—C13—C14	119.9 (3)
C4—C3—C2	116.5 (2)	C12—C13—H13	120.0
C4—C3—H3	121.8	C14—C13—H13	120.0
C2—C3—H3	121.8	C9—C14—C13	118.2 (3)
C3—C4—C5	122.9 (2)	C9—C14—H14	120.9
C3—C4—I	120.4 (2)	C13—C14—H14	120.9
C5—C4—I	116.7 (2)	C6—C15—H15A	109.5
C6—C5—C4	121.7 (2)	C6—C15—H15B	109.5
C6—C5—H5	119.2	H15A—C15—H15B	109.5
C4—C5—H5	119.2	C6—C15—H15C	109.5
C7—C6—C5	114.3 (2)	H15A—C15—H15C	109.5
C7—C6—C15	122.5 (2)	H15B—C15—H15C	109.5
C5—C6—C15	123.2 (2)	C8—C16—H16A	109.5
O1—C7—C2	110.6 (2)	C8—C16—H16B	109.5
O1—C7—C6	124.1 (2)	H16A—C16—H16B	109.5
C2—C7—C6	125.3 (2)	C8—C16—H16C	109.5
C1—C8—O1	110.3 (2)	H16A—C16—H16C	109.5
C1—C8—C16	134.8 (2)	H16B—C16—H16C	109.5

O2—S—C1—C8	−163.4 (2)	C5—C6—C7—O1	178.8 (2)
O3—S—C1—C8	−33.6 (3)	C15—C6—C7—O1	−2.7 (4)
C9—S—C1—C8	81.5 (2)	C5—C6—C7—C2	−1.7 (4)
O2—S—C1—C2	19.2 (2)	C15—C6—C7—C2	176.8 (2)
O3—S—C1—C2	149.0 (2)	C2—C1—C8—O1	−0.4 (3)
C9—S—C1—C2	−95.8 (2)	S—C1—C8—O1	−178.2 (2)
C8—C1—C2—C7	0.1 (3)	C2—C1—C8—C16	178.1 (3)
S—C1—C2—C7	177.8 (2)	S—C1—C8—C16	0.3 (4)
C8—C1—C2—C3	178.8 (3)	C7—O1—C8—C1	0.5 (3)
S—C1—C2—C3	−3.4 (4)	C7—O1—C8—C16	−178.3 (2)
C7—C2—C3—C4	−0.4 (3)	O2—S—C9—C14	−17.4 (2)
C1—C2—C3—C4	−179.1 (3)	O3—S—C9—C14	−147.6 (2)
C2—C3—C4—C5	−0.7 (4)	C1—S—C9—C14	96.7 (2)
C2—C3—C4—I	179.5 (2)	O2—S—C9—C10	161.6 (2)
C3—C4—C5—C6	0.7 (4)	O3—S—C9—C10	31.4 (2)
I—C4—C5—C6	−179.5 (2)	C1—S—C9—C10	−84.4 (2)
C4—C5—C6—C7	0.5 (4)	C14—C9—C10—C11	−0.9 (5)
C4—C5—C6—C15	−178.0 (2)	S—C9—C10—C11	−179.8 (3)
C8—O1—C7—C2	−0.5 (3)	C9—C10—C11—C12	0.3 (5)
C8—O1—C7—C6	179.0 (2)	C10—C11—C12—C13	0.3 (5)
C3—C2—C7—O1	−178.7 (2)	C11—C12—C13—C14	−0.3 (5)
C1—C2—C7—O1	0.3 (3)	C10—C9—C14—C13	0.8 (4)
C3—C2—C7—C6	1.7 (4)	S—C9—C14—C13	179.8 (2)
C1—C2—C7—C6	−179.3 (2)	C12—C13—C14—C9	−0.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱⁱ	0.95	2.59	3.382 (4)	141
C13—H13···O3ⁱⁱⁱ	0.95	2.44	3.342 (4)	159
C14—H14···O2	0.95	2.58	2.931 (4)	103
C16—H16B···O3	0.98	2.48	3.191 (4)	129

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃IO₃S
M_r	412.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	8.1165 (5), 14.0295 (9), 13.2470 (8)
β (°)	90.320 (1)
V (Å³)	1508.42 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.579, 0.641
No. of measured, independent and observed [I > 2σ(I)] reflections	9110, 3285, 3069
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.074, 0.99
No. of reflections	3285
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.13, −1.02

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
C11—H11···O1ⁱ	0.95	2.59	3.382 (4)	141.3
C13—H13···O3ⁱⁱ	0.95	2.44	3.342 (4)	158.6
C14—H14···O2	0.95	2.58	2.931 (4)	102.5
C16—H16B···O3	0.98	2.48	3.191 (4)	129.4

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

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o793. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o794. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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 5| May 2008| Page o930

doi:10.1107/S1600536808011240

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