2-Methyl-1-(4-methyl­phenyl­sulfon­yl)naphtho­[2,1-b]furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812012159

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1193

doi:10.1107/S1600536812012159

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2-Methyl-1-(4-methylphenylsulfonyl)naphtho[2,1-b]furan

Hong Dae Choi,^a Pil Ja Seo ^a 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 20 March 2012; accepted 21 March 2012; online 28 March 2012)

In the title compound, C₂₀H₁₆O₃S, the 4-methylphenyl ring makes a dihedral angle of 83.07 (3)° with the mean plane [r.m.s. deviation = 0.020 (1) Å] of the naphthofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 , 2012 ).

Experimental

Crystal data

C₂₀H₁₆O₃S
M_r = 336.39
Monoclinic, P 2₁ /n
a = 8.6628 (2) Å
b = 6.3669 (1) Å
c = 28.9119 (6) Å
β = 96.795 (1)°
V = 1583.44 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.35 × 0.32 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.676, T_max = 0.746
14714 measured reflections
3958 independent reflections
3363 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 1.04
3958 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14–C19 4-methylphenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.98	2.54	3.503 (2)	168
C13—H13C⋯O3ⁱⁱ	0.98	2.49	3.440 (2)	164
C5—H5⋯Cgⁱⁱⁱ	0.95	2.80	3.648 (2)	149
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y-1, z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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/S1600536812012159/hb6696sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012159/hb6696Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012159/hb6696Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2-methylnaphtho[2,1-b]furan derivatives containing 1-phenylsulfonyl (Choi et al., 2008) and 1-(4-methylphenylsulfinyl) (Choi et al., 2012) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.020 (1) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the naphthofuran fragment is 83.07 (3)°. The crystal packing features weak C—H···O hydrogen bonds (Fig. 2 & Table 1). In addition, weak C—H···π interactions occur (Fig. 2 & Table 1).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2012).

Experimental top

77% 3-Chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 2-methyl-1-(4-methylphenylsulfanyl)naphtho [2,1-b]furan (273 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (benzene) to afford the title compound as a colorless solid [yield 68%, m.p. 440–441 K; R_f = 0.41 (benzene)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Structure description top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2012).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) -x + 1, - y, - z; (ii) x, y - 1, z; (iii) x, y + 1, z.]

2-Methyl-1-(4-methylphenylsulfonyl)naphtho[2,1-b]furan top

Crystal data top

C₂₀H₁₆O₃S	F(000) = 704
M_r = 336.39	D_x = 1.411 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5369 reflections
a = 8.6628 (2) Å	θ = 2.4–28.2°
b = 6.3669 (1) Å	µ = 0.22 mm⁻¹
c = 28.9119 (6) Å	T = 173 K
β = 96.795 (1)°	Block, colourless
V = 1583.44 (6) Å³	0.35 × 0.32 × 0.28 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3958 independent reflections
Radiation source: rotating anode	3363 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.4°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
T_min = 0.676, T_max = 0.746	l = −38→36
14714 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0592P)² + 0.6896P] where P = (F_o² + 2F_c²)/3
3958 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₀H₁₆O₃S	V = 1583.44 (6) Å³
M_r = 336.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6628 (2) Å	µ = 0.22 mm⁻¹
b = 6.3669 (1) Å	T = 173 K
c = 28.9119 (6) Å	0.35 × 0.32 × 0.28 mm
β = 96.795 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3958 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3363 reflections with I > 2σ(I)
T_min = 0.676, T_max = 0.746	R_int = 0.029
14714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
3958 reflections	Δρ_min = −0.49 e Å⁻³
219 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.27965 (4)	0.47230 (6)	0.122492 (12)	0.02209 (11)
O1	0.53486 (13)	0.23737 (18)	0.03339 (4)	0.0289 (3)
O2	0.14170 (12)	0.35873 (19)	0.10517 (4)	0.0307 (3)
O3	0.26753 (12)	0.69453 (18)	0.12988 (4)	0.0298 (3)
C1	0.41907 (16)	0.4236 (2)	0.08492 (5)	0.0219 (3)
C2	0.56531 (16)	0.5295 (2)	0.07891 (5)	0.0213 (3)
C3	0.65037 (16)	0.7128 (2)	0.09593 (5)	0.0218 (3)
C4	0.60027 (17)	0.8614 (2)	0.12726 (5)	0.0247 (3)
H4	0.5033	0.8415	0.1389	0.030*
C5	0.68864 (19)	1.0335 (3)	0.14119 (6)	0.0295 (3)
H5	0.6519	1.1313	0.1622	0.035*
C6	0.83300 (19)	1.0672 (3)	0.12478 (6)	0.0332 (4)
H6	0.8936	1.1870	0.1345	0.040*
C7	0.88506 (18)	0.9260 (3)	0.09476 (6)	0.0316 (4)
H7	0.9831	0.9485	0.0840	0.038*
C8	0.79719 (16)	0.7470 (2)	0.07925 (5)	0.0254 (3)
C9	0.85486 (18)	0.6061 (3)	0.04712 (6)	0.0305 (3)
H9	0.9540	0.6316	0.0373	0.037*
C10	0.77213 (19)	0.4364 (3)	0.03018 (6)	0.0308 (3)
H10	0.8093	0.3442	0.0082	0.037*
C11	0.62874 (18)	0.4049 (2)	0.04693 (5)	0.0251 (3)
C12	0.40872 (18)	0.2496 (2)	0.05693 (5)	0.0260 (3)
C13	0.2966 (2)	0.0750 (3)	0.04686 (6)	0.0349 (4)
H13A	0.3285	−0.0119	0.0217	0.052*
H13B	0.1927	0.1325	0.0374	0.052*
H13C	0.2943	−0.0110	0.0749	0.052*
C14	0.35605 (16)	0.3550 (2)	0.17546 (5)	0.0218 (3)
C15	0.46746 (18)	0.4594 (3)	0.20557 (5)	0.0279 (3)
H15	0.4992	0.5975	0.1985	0.033*
C16	0.53175 (19)	0.3600 (3)	0.24596 (5)	0.0320 (4)
H16	0.6078	0.4310	0.2666	0.038*
C17	0.48649 (18)	0.1574 (3)	0.25668 (5)	0.0298 (3)
C18	0.37223 (19)	0.0579 (3)	0.22656 (6)	0.0291 (3)
H18	0.3380	−0.0784	0.2340	0.035*
C19	0.30745 (17)	0.1542 (2)	0.18583 (5)	0.0253 (3)
H19	0.2308	0.0838	0.1652	0.030*
C20	0.5594 (2)	0.0488 (3)	0.30016 (6)	0.0441 (5)
H20A	0.5242	0.1161	0.3275	0.066*
H20B	0.6729	0.0591	0.3020	0.066*
H20C	0.5287	−0.0994	0.2992	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01901 (17)	0.0225 (2)	0.02499 (19)	−0.00027 (13)	0.00374 (13)	0.00294 (13)
O1	0.0367 (6)	0.0263 (6)	0.0254 (5)	−0.0045 (5)	0.0102 (4)	−0.0036 (4)
O2	0.0212 (5)	0.0360 (7)	0.0345 (6)	−0.0048 (5)	0.0009 (4)	0.0022 (5)
O3	0.0270 (5)	0.0233 (6)	0.0403 (6)	0.0038 (4)	0.0093 (5)	0.0044 (5)
C1	0.0227 (6)	0.0237 (7)	0.0195 (6)	−0.0006 (5)	0.0028 (5)	0.0026 (5)
C2	0.0217 (6)	0.0232 (7)	0.0193 (6)	0.0012 (5)	0.0031 (5)	0.0034 (5)
C3	0.0210 (6)	0.0231 (7)	0.0210 (6)	0.0007 (5)	0.0014 (5)	0.0047 (5)
C4	0.0240 (7)	0.0236 (7)	0.0266 (7)	0.0005 (6)	0.0037 (5)	0.0011 (6)
C5	0.0308 (8)	0.0261 (8)	0.0313 (8)	−0.0006 (6)	0.0030 (6)	−0.0022 (6)
C6	0.0299 (8)	0.0312 (9)	0.0375 (9)	−0.0099 (7)	0.0004 (6)	−0.0011 (7)
C7	0.0241 (7)	0.0358 (9)	0.0352 (8)	−0.0076 (6)	0.0048 (6)	0.0033 (7)
C8	0.0220 (6)	0.0291 (8)	0.0249 (7)	−0.0004 (6)	0.0026 (5)	0.0041 (6)
C9	0.0257 (7)	0.0366 (9)	0.0309 (8)	0.0011 (7)	0.0108 (6)	0.0043 (7)
C10	0.0331 (8)	0.0327 (9)	0.0286 (8)	0.0022 (7)	0.0124 (6)	0.0000 (6)
C11	0.0301 (7)	0.0234 (7)	0.0225 (7)	−0.0016 (6)	0.0056 (6)	0.0014 (6)
C12	0.0316 (7)	0.0256 (8)	0.0210 (7)	−0.0037 (6)	0.0042 (5)	0.0015 (6)
C13	0.0430 (9)	0.0297 (9)	0.0326 (8)	−0.0117 (7)	0.0066 (7)	−0.0041 (7)
C14	0.0233 (6)	0.0215 (7)	0.0216 (6)	0.0020 (5)	0.0061 (5)	0.0003 (5)
C15	0.0312 (7)	0.0259 (8)	0.0268 (7)	−0.0050 (6)	0.0048 (6)	−0.0002 (6)
C16	0.0334 (8)	0.0370 (9)	0.0250 (7)	−0.0034 (7)	0.0007 (6)	−0.0018 (7)
C17	0.0316 (8)	0.0362 (9)	0.0227 (7)	0.0050 (7)	0.0080 (6)	0.0045 (6)
C18	0.0339 (8)	0.0253 (8)	0.0297 (8)	0.0003 (6)	0.0097 (6)	0.0033 (6)
C19	0.0274 (7)	0.0231 (7)	0.0262 (7)	−0.0024 (6)	0.0069 (6)	0.0000 (6)
C20	0.0469 (10)	0.0543 (12)	0.0306 (9)	0.0023 (9)	0.0021 (8)	0.0138 (8)

Geometric parameters (Å, º) top

S1—O2	1.4354 (11)	C9—H9	0.9500
S1—O3	1.4366 (12)	C10—C11	1.400 (2)
S1—C1	1.7450 (15)	C10—H10	0.9500
S1—C14	1.7611 (15)	C12—C13	1.483 (2)
O1—C12	1.3562 (18)	C13—H13A	0.9800
O1—C11	1.3700 (18)	C13—H13B	0.9800
C1—C12	1.369 (2)	C13—H13C	0.9800
C1—C2	1.4632 (19)	C14—C19	1.390 (2)
C2—C11	1.381 (2)	C14—C15	1.390 (2)
C2—C3	1.436 (2)	C15—C16	1.386 (2)
C3—C4	1.413 (2)	C15—H15	0.9500
C3—C8	1.4293 (19)	C16—C17	1.394 (2)
C4—C5	1.370 (2)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.391 (2)
C5—C6	1.405 (2)	C17—C20	1.506 (2)
C5—H5	0.9500	C18—C19	1.386 (2)
C6—C7	1.363 (2)	C18—H18	0.9500
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.414 (2)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C8—C9	1.424 (2)	C20—H20C	0.9800
C9—C10	1.355 (2)

O2—S1—O3	118.39 (7)	O1—C11—C2	111.64 (13)
O2—S1—C1	107.60 (7)	O1—C11—C10	122.26 (14)
O3—S1—C1	109.60 (7)	C2—C11—C10	126.08 (15)
O2—S1—C14	107.55 (7)	O1—C12—C1	110.07 (13)
O3—S1—C14	108.36 (7)	O1—C12—C13	113.98 (13)
C1—S1—C14	104.45 (7)	C1—C12—C13	135.95 (15)
C12—O1—C11	107.34 (11)	C12—C13—H13A	109.5
C12—C1—C2	107.44 (13)	C12—C13—H13B	109.5
C12—C1—S1	120.67 (11)	H13A—C13—H13B	109.5
C2—C1—S1	131.67 (11)	C12—C13—H13C	109.5
C11—C2—C3	117.89 (13)	H13A—C13—H13C	109.5
C11—C2—C1	103.51 (13)	H13B—C13—H13C	109.5
C3—C2—C1	138.60 (13)	C19—C14—C15	120.70 (14)
C4—C3—C8	117.86 (13)	C19—C14—S1	119.04 (11)
C4—C3—C2	125.43 (13)	C15—C14—S1	120.22 (12)
C8—C3—C2	116.70 (13)	C16—C15—C14	119.28 (15)
C5—C4—C3	121.38 (14)	C16—C15—H15	120.4
C5—C4—H4	119.3	C14—C15—H15	120.4
C3—C4—H4	119.3	C15—C16—C17	120.97 (15)
C4—C5—C6	120.75 (15)	C15—C16—H16	119.5
C4—C5—H5	119.6	C17—C16—H16	119.5
C6—C5—H5	119.6	C18—C17—C16	118.70 (14)
C7—C6—C5	119.30 (15)	C18—C17—C20	120.71 (16)
C7—C6—H6	120.4	C16—C17—C20	120.59 (16)
C5—C6—H6	120.4	C19—C18—C17	121.13 (15)
C6—C7—C8	121.82 (15)	C19—C18—H18	119.4
C6—C7—H7	119.1	C17—C18—H18	119.4
C8—C7—H7	119.1	C18—C19—C14	119.19 (14)
C7—C8—C9	119.84 (14)	C18—C19—H19	120.4
C7—C8—C3	118.89 (14)	C14—C19—H19	120.4
C9—C8—C3	121.26 (14)	C17—C20—H20A	109.5
C10—C9—C8	121.78 (14)	C17—C20—H20B	109.5
C10—C9—H9	119.1	H20A—C20—H20B	109.5
C8—C9—H9	119.1	C17—C20—H20C	109.5
C9—C10—C11	116.24 (15)	H20A—C20—H20C	109.5
C9—C10—H10	121.9	H20B—C20—H20C	109.5
C11—C10—H10	121.9

O2—S1—C1—C12	−21.68 (14)	C12—O1—C11—C10	178.08 (15)
O3—S1—C1—C12	−151.66 (12)	C3—C2—C11—O1	−179.34 (12)
C14—S1—C1—C12	92.43 (13)	C1—C2—C11—O1	0.22 (16)
O2—S1—C1—C2	164.56 (13)	C3—C2—C11—C10	2.0 (2)
O3—S1—C1—C2	34.58 (16)	C1—C2—C11—C10	−178.40 (15)
C14—S1—C1—C2	−81.34 (15)	C9—C10—C11—O1	−178.71 (15)
C12—C1—C2—C11	0.24 (16)	C9—C10—C11—C2	−0.2 (2)
S1—C1—C2—C11	174.62 (12)	C11—O1—C12—C1	0.76 (16)
C12—C1—C2—C3	179.65 (17)	C11—O1—C12—C13	−178.63 (13)
S1—C1—C2—C3	−6.0 (3)	C2—C1—C12—O1	−0.62 (17)
C11—C2—C3—C4	177.50 (14)	S1—C1—C12—O1	−175.75 (10)
C1—C2—C3—C4	−1.8 (3)	C2—C1—C12—C13	178.57 (17)
C11—C2—C3—C8	−2.0 (2)	S1—C1—C12—C13	3.4 (3)
C1—C2—C3—C8	178.65 (16)	O2—S1—C14—C19	17.39 (14)
C8—C3—C4—C5	0.3 (2)	O3—S1—C14—C19	146.47 (11)
C2—C3—C4—C5	−179.20 (14)	C1—S1—C14—C19	−96.75 (12)
C3—C4—C5—C6	−0.3 (2)	O2—S1—C14—C15	−164.89 (12)
C4—C5—C6—C7	−0.1 (3)	O3—S1—C14—C15	−35.81 (14)
C5—C6—C7—C8	0.6 (3)	C1—S1—C14—C15	80.97 (13)
C6—C7—C8—C9	178.71 (15)	C19—C14—C15—C16	0.9 (2)
C6—C7—C8—C3	−0.6 (2)	S1—C14—C15—C16	−176.78 (12)
C4—C3—C8—C7	0.1 (2)	C14—C15—C16—C17	0.1 (2)
C2—C3—C8—C7	179.66 (13)	C15—C16—C17—C18	−1.6 (2)
C4—C3—C8—C9	−179.15 (14)	C15—C16—C17—C20	178.72 (16)
C2—C3—C8—C9	0.4 (2)	C16—C17—C18—C19	2.1 (2)
C7—C8—C9—C10	−177.80 (16)	C20—C17—C18—C19	−178.24 (15)
C3—C8—C9—C10	1.5 (2)	C17—C18—C19—C14	−1.1 (2)
C8—C9—C10—C11	−1.5 (2)	C15—C14—C19—C18	−0.4 (2)
C12—O1—C11—C2	−0.60 (17)	S1—C14—C19—C18	177.28 (11)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C14–C19 4-methylphenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.98	2.54	3.503 (2)	168
C13—H13C···O3ⁱⁱ	0.98	2.49	3.440 (2)	164
C5—H5···Cgⁱⁱⁱ	0.95	2.80	3.648 (2)	149

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₃S
M_r	336.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	8.6628 (2), 6.3669 (1), 28.9119 (6)
β (°)	96.795 (1)
V (Å³)	1583.44 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.35 × 0.32 × 0.28

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.676, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14714, 3958, 3363
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 1.04
No. of reflections	3958
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.49

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C14–C19 4-methylphenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.98	2.54	3.503 (2)	168
C13—H13C···O3ⁱⁱ	0.98	2.49	3.440 (2)	164
C5—H5···Cgⁱⁱⁱ	0.95	2.80	3.648 (2)	149

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

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o549. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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 68| Part 4| April 2012| Page o1193

doi:10.1107/S1600536812012159

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