3-(3-Chloro­phenyl­sulfon­yl)-2,5,7-trimethyl-1-benzofuran

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

doi:10.1107/S1600536812008355

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o945

doi:10.1107/S1600536812008355

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3-(3-Chlorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran

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 21 February 2012; accepted 24 February 2012; online 3 March 2012)

In the title compound, C₁₇H₁₅ClO₃S, the 3-chlorophenyl ring makes a dihedral angle of 77.76 (6)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular 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 , 2010 ); Seo et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₅ClO₃S
M_r = 334.80
Monoclinic, P 2₁ /c
a = 14.5299 (3) Å
b = 12.9778 (2) Å
c = 8.1776 (1) Å
β = 92.615 (1)°
V = 1540.41 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 173 K
0.36 × 0.29 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.872, T_max = 0.908
14420 measured reflections
3551 independent reflections
3053 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.04
3551 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.31 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/C2/C7/O1/C8 furan ring and the C12–C17 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3ⁱ	0.95	2.60	3.264 (2)	127
C10—H10A⋯Cg2ⁱⁱ	0.98	2.86	3.704 (2)	145
C10—H10C⋯Cg1ⁱⁱ	0.98	3.08	3.536 (2)	110
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536812008355/bh2417sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008355/bh2417Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008355/bh2417Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2,5,7-trimethyl-1-benzofuran derivatives containing 3-phenylsulfonyl (Choi et al., 2008), 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) and 3-(3-fluorophenylsulfonyl) (Seo et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-chlorophenyl ring and the mean plane of the benzofuran fragment is 77.76 (6)°. The crystal packing is stabilized by weak intermolecular C–H···O hydrogen bonds (Fig. 2 & Table 1). The crystal packing is further stabilized by intermolecular C–H···π interactions (Fig.3 & Table 1, Cg1 and Cg2 are the centroids of the C1/C2/ C7/O1/C8 furan ring and the C12-C17 benzene ring, respectively).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2010); Seo et al. (2011).

Experimental top

77% 3-Chloroperoxybenzoic acid (493 mg, 2.2 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (333 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10 h., 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 71%, m.p. 413-414 K; R_f= 0.46 (benzene)]. Single crystals suitable for X-ray diffraction 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, 2010); Seo et al. (2011).

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 interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. Symmetry code: (i) -x+1, -y+1, -z+2].
	Fig. 3. A view of the 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: (ii) x, -y +3/2, z-1/2; (iii) x, -y+3/2, z+1/2].

3-(3-Chlorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅ClO₃S	F(000) = 696
M_r = 334.80	D_x = 1.444 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 413 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.5299 (3) Å	Cell parameters from 7514 reflections
b = 12.9778 (2) Å	θ = 2.8–27.4°
c = 8.1776 (1) Å	µ = 0.39 mm⁻¹
β = 92.615 (1)°	T = 173 K
V = 1540.41 (4) Å³	Block, colourless
Z = 4	0.36 × 0.29 × 0.25 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3551 independent reflections
Radiation source: rotating anode	3053 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.028
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.4°
φ and ω scans	h = −15→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→16
T_min = 0.872, T_max = 0.908	l = −10→10
14420 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0542P)² + 0.775P] where P = (F_o² + 2F_c²)/3
3551 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³
0 constraints

Crystal data top

C₁₇H₁₅ClO₃S	V = 1540.41 (4) Å³
M_r = 334.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5299 (3) Å	µ = 0.39 mm⁻¹
b = 12.9778 (2) Å	T = 173 K
c = 8.1776 (1) Å	0.36 × 0.29 × 0.25 mm
β = 92.615 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3551 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3053 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.908	R_int = 0.028
14420 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	Δρ_max = 0.31 e Å⁻³
3551 reflections	Δρ_min = −0.41 e Å⁻³
202 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.11297 (3)	0.26899 (4)	0.95927 (6)	0.03925 (14)
S1	0.38836 (3)	0.46155 (3)	0.65400 (5)	0.02434 (12)
O1	0.32039 (8)	0.75011 (9)	0.56955 (15)	0.0285 (3)
O2	0.35944 (9)	0.38758 (10)	0.53201 (14)	0.0313 (3)
O3	0.48438 (8)	0.47396 (10)	0.69791 (15)	0.0325 (3)
C1	0.34200 (11)	0.57998 (13)	0.59670 (19)	0.0242 (3)
C2	0.25351 (11)	0.59471 (13)	0.51051 (18)	0.0234 (3)
C3	0.18368 (12)	0.53119 (13)	0.4455 (2)	0.0265 (4)
H3	0.1880	0.4584	0.4548	0.032*
C4	0.10747 (12)	0.57732 (15)	0.3666 (2)	0.0297 (4)
C5	0.10147 (12)	0.68466 (15)	0.3578 (2)	0.0305 (4)
H5	0.0485	0.7142	0.3040	0.037*
C6	0.16886 (12)	0.75061 (14)	0.4236 (2)	0.0281 (4)
C7	0.24429 (11)	0.70102 (13)	0.49726 (19)	0.0252 (3)
C8	0.37838 (12)	0.67465 (14)	0.6292 (2)	0.0278 (4)
C9	0.03198 (14)	0.51129 (17)	0.2890 (3)	0.0404 (5)
H9A	0.0450	0.4981	0.1743	0.061*
H9B	−0.0271	0.5472	0.2943	0.061*
H9C	0.0291	0.4457	0.3479	0.061*
C10	0.16093 (14)	0.86578 (15)	0.4170 (3)	0.0381 (4)
H10A	0.1800	0.8948	0.5239	0.057*
H10B	0.0969	0.8851	0.3895	0.057*
H10C	0.2007	0.8927	0.3334	0.057*
C11	0.46509 (13)	0.71222 (16)	0.7113 (3)	0.0385 (4)
H11A	0.4854	0.6634	0.7970	0.058*
H11B	0.4544	0.7798	0.7606	0.058*
H11C	0.5127	0.7183	0.6308	0.058*
C12	0.33205 (11)	0.42967 (13)	0.83512 (19)	0.0241 (3)
C13	0.36775 (12)	0.46631 (15)	0.9846 (2)	0.0300 (4)
H13	0.4209	0.5090	0.9896	0.036*
C14	0.32471 (13)	0.43965 (16)	1.1264 (2)	0.0335 (4)
H14	0.3488	0.4634	1.2296	0.040*
C15	0.24674 (13)	0.37856 (14)	1.1179 (2)	0.0308 (4)
H15	0.2174	0.3597	1.2150	0.037*
C16	0.21193 (12)	0.34517 (13)	0.9675 (2)	0.0273 (4)
C17	0.25354 (11)	0.36921 (13)	0.8236 (2)	0.0253 (3)
H17	0.2292	0.3452	0.7208	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0390 (3)	0.0409 (3)	0.0380 (3)	−0.0132 (2)	0.0041 (2)	0.0024 (2)
S1	0.0259 (2)	0.0245 (2)	0.0226 (2)	0.00192 (15)	0.00121 (15)	0.00141 (15)
O1	0.0278 (6)	0.0236 (6)	0.0338 (7)	−0.0011 (5)	−0.0036 (5)	0.0008 (5)
O2	0.0416 (7)	0.0275 (7)	0.0249 (6)	0.0006 (5)	0.0037 (5)	−0.0028 (5)
O3	0.0252 (6)	0.0372 (7)	0.0352 (7)	0.0032 (5)	0.0020 (5)	0.0056 (6)
C1	0.0245 (8)	0.0261 (9)	0.0219 (7)	0.0003 (6)	−0.0005 (6)	0.0014 (6)
C2	0.0245 (8)	0.0262 (8)	0.0196 (7)	0.0003 (6)	0.0021 (6)	0.0008 (6)
C3	0.0291 (8)	0.0255 (9)	0.0249 (8)	−0.0021 (7)	0.0016 (6)	−0.0008 (7)
C4	0.0263 (8)	0.0377 (10)	0.0251 (8)	−0.0039 (7)	−0.0003 (7)	−0.0010 (7)
C5	0.0242 (8)	0.0373 (10)	0.0298 (8)	0.0037 (7)	−0.0003 (7)	0.0040 (7)
C6	0.0278 (8)	0.0295 (9)	0.0273 (8)	0.0036 (7)	0.0040 (7)	0.0039 (7)
C7	0.0262 (8)	0.0260 (9)	0.0233 (8)	−0.0019 (6)	0.0006 (6)	0.0002 (7)
C8	0.0275 (8)	0.0283 (9)	0.0273 (8)	0.0005 (7)	−0.0008 (7)	0.0011 (7)
C9	0.0328 (10)	0.0460 (12)	0.0417 (11)	−0.0079 (9)	−0.0073 (8)	−0.0002 (9)
C10	0.0379 (10)	0.0305 (10)	0.0456 (11)	0.0052 (8)	0.0001 (8)	0.0059 (8)
C11	0.0329 (9)	0.0353 (11)	0.0463 (11)	−0.0057 (8)	−0.0092 (8)	−0.0038 (9)
C12	0.0254 (8)	0.0240 (8)	0.0227 (7)	0.0033 (6)	0.0005 (6)	0.0014 (6)
C13	0.0258 (8)	0.0373 (10)	0.0263 (8)	−0.0014 (7)	−0.0033 (7)	−0.0013 (7)
C14	0.0361 (10)	0.0419 (11)	0.0220 (8)	0.0005 (8)	−0.0038 (7)	−0.0032 (7)
C15	0.0360 (9)	0.0336 (10)	0.0229 (8)	0.0031 (7)	0.0035 (7)	0.0021 (7)
C16	0.0285 (8)	0.0235 (8)	0.0298 (8)	−0.0006 (7)	0.0013 (7)	0.0018 (7)
C17	0.0305 (8)	0.0230 (8)	0.0221 (7)	0.0010 (7)	−0.0019 (6)	−0.0007 (6)

Geometric parameters (Å, º) top

Cl1—C16	1.7437 (18)	C9—H9A	0.9800
S1—O2	1.4336 (13)	C9—H9B	0.9800
S1—O3	1.4337 (13)	C9—H9C	0.9800
S1—C1	1.7341 (17)	C10—H10A	0.9800
S1—C12	1.7734 (16)	C10—H10B	0.9800
O1—C8	1.367 (2)	C10—H10C	0.9800
O1—C7	1.385 (2)	C11—H11A	0.9800
C1—C8	1.359 (2)	C11—H11B	0.9800
C1—C2	1.450 (2)	C11—H11C	0.9800
C2—C7	1.390 (2)	C12—C17	1.384 (2)
C2—C3	1.394 (2)	C12—C13	1.390 (2)
C3—C4	1.391 (2)	C13—C14	1.386 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.397 (3)	C14—C15	1.382 (3)
C4—C9	1.509 (3)	C14—H14	0.9500
C5—C6	1.390 (3)	C15—C16	1.378 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.385 (2)	C16—C17	1.383 (2)
C6—C10	1.500 (3)	C17—H17	0.9500
C8—C11	1.483 (2)

O2—S1—O3	120.04 (8)	C4—C9—H9C	109.5
O2—S1—C1	107.91 (8)	H9A—C9—H9C	109.5
O3—S1—C1	109.25 (8)	H9B—C9—H9C	109.5
O2—S1—C12	107.05 (8)	C6—C10—H10A	109.5
O3—S1—C12	107.32 (8)	C6—C10—H10B	109.5
C1—S1—C12	104.13 (8)	H10A—C10—H10B	109.5
C8—O1—C7	106.84 (13)	C6—C10—H10C	109.5
C8—C1—C2	107.71 (15)	H10A—C10—H10C	109.5
C8—C1—S1	127.28 (13)	H10B—C10—H10C	109.5
C2—C1—S1	124.96 (13)	C8—C11—H11A	109.5
C7—C2—C3	119.44 (15)	C8—C11—H11B	109.5
C7—C2—C1	104.41 (15)	H11A—C11—H11B	109.5
C3—C2—C1	136.15 (16)	C8—C11—H11C	109.5
C4—C3—C2	118.20 (16)	H11A—C11—H11C	109.5
C4—C3—H3	120.9	H11B—C11—H11C	109.5
C2—C3—H3	120.9	C17—C12—C13	121.80 (15)
C3—C4—C5	119.95 (16)	C17—C12—S1	119.06 (12)
C3—C4—C9	119.90 (17)	C13—C12—S1	119.14 (13)
C5—C4—C9	120.15 (17)	C14—C13—C12	119.07 (16)
C6—C5—C4	123.56 (16)	C14—C13—H13	120.5
C6—C5—H5	118.2	C12—C13—H13	120.5
C4—C5—H5	118.2	C15—C14—C13	120.09 (16)
C7—C6—C5	114.31 (16)	C15—C14—H14	120.0
C7—C6—C10	122.45 (17)	C13—C14—H14	120.0
C5—C6—C10	123.24 (17)	C16—C15—C14	119.46 (16)
C6—C7—O1	124.92 (16)	C16—C15—H15	120.3
C6—C7—C2	124.52 (16)	C14—C15—H15	120.3
O1—C7—C2	110.55 (14)	C15—C16—C17	122.10 (16)
C1—C8—O1	110.49 (14)	C15—C16—Cl1	118.76 (13)
C1—C8—C11	134.48 (17)	C17—C16—Cl1	119.14 (13)
O1—C8—C11	115.03 (15)	C16—C17—C12	117.46 (15)
C4—C9—H9A	109.5	C16—C17—H17	121.3
C4—C9—H9B	109.5	C12—C17—H17	121.3
H9A—C9—H9B	109.5

O2—S1—C1—C8	−149.77 (15)	C1—C2—C7—C6	−179.53 (15)
O3—S1—C1—C8	−17.69 (18)	C3—C2—C7—O1	179.81 (14)
C12—S1—C1—C8	96.71 (17)	C1—C2—C7—O1	−0.22 (18)
O2—S1—C1—C2	33.36 (16)	C2—C1—C8—O1	−0.38 (19)
O3—S1—C1—C2	165.44 (13)	S1—C1—C8—O1	−177.69 (12)
C12—S1—C1—C2	−80.16 (15)	C2—C1—C8—C11	−179.72 (19)
C8—C1—C2—C7	0.36 (18)	S1—C1—C8—C11	3.0 (3)
S1—C1—C2—C7	177.75 (12)	C7—O1—C8—C1	0.25 (18)
C8—C1—C2—C3	−179.68 (18)	C7—O1—C8—C11	179.72 (15)
S1—C1—C2—C3	−2.3 (3)	O2—S1—C12—C17	−20.30 (15)
C7—C2—C3—C4	1.1 (2)	O3—S1—C12—C17	−150.40 (13)
C1—C2—C3—C4	−178.86 (17)	C1—S1—C12—C17	93.83 (14)
C2—C3—C4—C5	−1.6 (2)	O2—S1—C12—C13	159.90 (14)
C2—C3—C4—C9	177.74 (16)	O3—S1—C12—C13	29.80 (16)
C3—C4—C5—C6	0.5 (3)	C1—S1—C12—C13	−85.96 (15)
C9—C4—C5—C6	−178.82 (17)	C17—C12—C13—C14	1.5 (3)
C4—C5—C6—C7	1.0 (3)	S1—C12—C13—C14	−178.74 (14)
C4—C5—C6—C10	−178.55 (18)	C12—C13—C14—C15	−0.8 (3)
C5—C6—C7—O1	179.26 (15)	C13—C14—C15—C16	−0.5 (3)
C10—C6—C7—O1	−1.2 (3)	C14—C15—C16—C17	1.2 (3)
C5—C6—C7—C2	−1.5 (2)	C14—C15—C16—Cl1	−179.50 (15)
C10—C6—C7—C2	178.05 (17)	C15—C16—C17—C12	−0.6 (3)
C8—O1—C7—C6	179.31 (16)	Cl1—C16—C17—C12	−179.88 (13)
C8—O1—C7—C2	0.00 (18)	C13—C12—C17—C16	−0.8 (2)
C3—C2—C7—C6	0.5 (3)	S1—C12—C17—C16	179.45 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C12-C17 benzene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3ⁱ	0.95	2.60	3.264 (2)	127
C10—H10A···Cg2ⁱⁱ	0.98	2.86	3.704 (2)	145
C10—H10C···Cg1ⁱⁱ	0.98	3.08	3.536 (2)	110

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClO₃S
M_r	334.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	14.5299 (3), 12.9778 (2), 8.1776 (1)
β (°)	92.615 (1)
V (Å³)	1540.41 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.36 × 0.29 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.872, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	14420, 3551, 3053
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.04
No. of reflections	3551
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.41

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

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C12-C17 benzene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3ⁱ	0.95	2.60	3.264 (2)	127.4
C10—H10A···Cg2ⁱⁱ	0.98	2.86	3.704 (2)	144.9
C10—H10C···Cg1ⁱⁱ	0.98	3.08	3.536 (2)	109.7

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

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., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o794. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1813. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3359. Web of Science CSD 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 o945

doi:10.1107/S1600536812008355

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