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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o945
doi:10.1107/S1600536812008355

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

Hong Dae Choi,a Pil Ja Seoa and Uk Leeb*

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[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o794.], 2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1813.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3359.]).

[Scheme 1]

Experimental

Crystal data

  • C17H15ClO3S

  • Mr = 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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.872, Tmax = 0.908

  • 14420 measured reflections

  • 3551 independent reflections

  • 3053 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.04

  • 3551 reflections

  • 202 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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; Rf= 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.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. Uiso(H) =1.2Ueq(C) for aryl and 1.5Ueq(C)for methyl H atoms.

Structure description 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).

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
[Figure 1] 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.
[Figure 2] 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].
[Figure 3] 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
C17H15ClO3SF(000) = 696
Mr = 334.80Dx = 1.444 Mg m−3
Monoclinic, P21/cMelting point: 413 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.5299 (3) ÅCell parameters from 7514 reflections
b = 12.9778 (2) Åθ = 2.8–27.4°
c = 8.1776 (1) ŵ = 0.39 mm−1
β = 92.615 (1)°T = 173 K
V = 1540.41 (4) Å3Block, colourless
Z = 40.36 × 0.29 × 0.25 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		3551 independent reflections
Radiation source: rotating anode3053 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.028
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.4°
φ and ω scansh = −15→18
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −15→16
Tmin = 0.872, Tmax = 0.908l = −10→10
14420 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.105H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.775P]
where P = (Fo2 + 2Fc2)/3
3551 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.41 e Å−3
0 constraints
Crystal data top
C17H15ClO3SV = 1540.41 (4) Å3
Mr = 334.80Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.5299 (3) ŵ = 0.39 mm−1
b = 12.9778 (2) ÅT = 173 K
c = 8.1776 (1) Å0.36 × 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)
Tmin = 0.872, Tmax = 0.908Rint = 0.028
14420 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.04Δρmax = 0.31 e Å−3
3551 reflectionsΔρmin = −0.41 e Å−3
202 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.11297 (3)0.26899 (4)0.95927 (6)0.03925 (14)
S10.38836 (3)0.46155 (3)0.65400 (5)0.02434 (12)
O10.32039 (8)0.75011 (9)0.56955 (15)0.0285 (3)
O20.35944 (9)0.38758 (10)0.53201 (14)0.0313 (3)
O30.48438 (8)0.47396 (10)0.69791 (15)0.0325 (3)
C10.34200 (11)0.57998 (13)0.59670 (19)0.0242 (3)
C20.25351 (11)0.59471 (13)0.51051 (18)0.0234 (3)
C30.18368 (12)0.53119 (13)0.4455 (2)0.0265 (4)
H30.18800.45840.45480.032*
C40.10747 (12)0.57732 (15)0.3666 (2)0.0297 (4)
C50.10147 (12)0.68466 (15)0.3578 (2)0.0305 (4)
H50.04850.71420.30400.037*
C60.16886 (12)0.75061 (14)0.4236 (2)0.0281 (4)
C70.24429 (11)0.70102 (13)0.49726 (19)0.0252 (3)
C80.37838 (12)0.67465 (14)0.6292 (2)0.0278 (4)
C90.03198 (14)0.51129 (17)0.2890 (3)0.0404 (5)
H9A0.04500.49810.17430.061*
H9B−0.02710.54720.29430.061*
H9C0.02910.44570.34790.061*
C100.16093 (14)0.86578 (15)0.4170 (3)0.0381 (4)
H10A0.18000.89480.52390.057*
H10B0.09690.88510.38950.057*
H10C0.20070.89270.33340.057*
C110.46509 (13)0.71222 (16)0.7113 (3)0.0385 (4)
H11A0.48540.66340.79700.058*
H11B0.45440.77980.76060.058*
H11C0.51270.71830.63080.058*
C120.33205 (11)0.42967 (13)0.83512 (19)0.0241 (3)
C130.36775 (12)0.46631 (15)0.9846 (2)0.0300 (4)
H130.42090.50900.98960.036*
C140.32471 (13)0.43965 (16)1.1264 (2)0.0335 (4)
H140.34880.46341.22960.040*
C150.24674 (13)0.37856 (14)1.1179 (2)0.0308 (4)
H150.21740.35971.21500.037*
C160.21193 (12)0.34517 (13)0.9675 (2)0.0273 (4)
C170.25354 (11)0.36921 (13)0.8236 (2)0.0253 (3)
H170.22920.34520.72080.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0390 (3)0.0409 (3)0.0380 (3)−0.0132 (2)0.0041 (2)0.0024 (2)
S10.0259 (2)0.0245 (2)0.0226 (2)0.00192 (15)0.00121 (15)0.00141 (15)
O10.0278 (6)0.0236 (6)0.0338 (7)−0.0011 (5)−0.0036 (5)0.0008 (5)
O20.0416 (7)0.0275 (7)0.0249 (6)0.0006 (5)0.0037 (5)−0.0028 (5)
O30.0252 (6)0.0372 (7)0.0352 (7)0.0032 (5)0.0020 (5)0.0056 (6)
C10.0245 (8)0.0261 (9)0.0219 (7)0.0003 (6)−0.0005 (6)0.0014 (6)
C20.0245 (8)0.0262 (8)0.0196 (7)0.0003 (6)0.0021 (6)0.0008 (6)
C30.0291 (8)0.0255 (9)0.0249 (8)−0.0021 (7)0.0016 (6)−0.0008 (7)
C40.0263 (8)0.0377 (10)0.0251 (8)−0.0039 (7)−0.0003 (7)−0.0010 (7)
C50.0242 (8)0.0373 (10)0.0298 (8)0.0037 (7)−0.0003 (7)0.0040 (7)
C60.0278 (8)0.0295 (9)0.0273 (8)0.0036 (7)0.0040 (7)0.0039 (7)
C70.0262 (8)0.0260 (9)0.0233 (8)−0.0019 (6)0.0006 (6)0.0002 (7)
C80.0275 (8)0.0283 (9)0.0273 (8)0.0005 (7)−0.0008 (7)0.0011 (7)
C90.0328 (10)0.0460 (12)0.0417 (11)−0.0079 (9)−0.0073 (8)−0.0002 (9)
C100.0379 (10)0.0305 (10)0.0456 (11)0.0052 (8)0.0001 (8)0.0059 (8)
C110.0329 (9)0.0353 (11)0.0463 (11)−0.0057 (8)−0.0092 (8)−0.0038 (9)
C120.0254 (8)0.0240 (8)0.0227 (7)0.0033 (6)0.0005 (6)0.0014 (6)
C130.0258 (8)0.0373 (10)0.0263 (8)−0.0014 (7)−0.0033 (7)−0.0013 (7)
C140.0361 (10)0.0419 (11)0.0220 (8)0.0005 (8)−0.0038 (7)−0.0032 (7)
C150.0360 (9)0.0336 (10)0.0229 (8)0.0031 (7)0.0035 (7)0.0021 (7)
C160.0285 (8)0.0235 (8)0.0298 (8)−0.0006 (7)0.0013 (7)0.0018 (7)
C170.0305 (8)0.0230 (8)0.0221 (7)0.0010 (7)−0.0019 (6)−0.0007 (6)
Geometric parameters (Å, º) top
Cl1—C161.7437 (18)C9—H9A0.9800
S1—O21.4336 (13)C9—H9B0.9800
S1—O31.4337 (13)C9—H9C0.9800
S1—C11.7341 (17)C10—H10A0.9800
S1—C121.7734 (16)C10—H10B0.9800
O1—C81.367 (2)C10—H10C0.9800
O1—C71.385 (2)C11—H11A0.9800
C1—C81.359 (2)C11—H11B0.9800
C1—C21.450 (2)C11—H11C0.9800
C2—C71.390 (2)C12—C171.384 (2)
C2—C31.394 (2)C12—C131.390 (2)
C3—C41.391 (2)C13—C141.386 (2)
C3—H30.9500C13—H130.9500
C4—C51.397 (3)C14—C151.382 (3)
C4—C91.509 (3)C14—H140.9500
C5—C61.390 (3)C15—C161.378 (2)
C5—H50.9500C15—H150.9500
C6—C71.385 (2)C16—C171.383 (2)
C6—C101.500 (3)C17—H170.9500
C8—C111.483 (2)
O2—S1—O3120.04 (8)C4—C9—H9C109.5
O2—S1—C1107.91 (8)H9A—C9—H9C109.5
O3—S1—C1109.25 (8)H9B—C9—H9C109.5
O2—S1—C12107.05 (8)C6—C10—H10A109.5
O3—S1—C12107.32 (8)C6—C10—H10B109.5
C1—S1—C12104.13 (8)H10A—C10—H10B109.5
C8—O1—C7106.84 (13)C6—C10—H10C109.5
C8—C1—C2107.71 (15)H10A—C10—H10C109.5
C8—C1—S1127.28 (13)H10B—C10—H10C109.5
C2—C1—S1124.96 (13)C8—C11—H11A109.5
C7—C2—C3119.44 (15)C8—C11—H11B109.5
C7—C2—C1104.41 (15)H11A—C11—H11B109.5
C3—C2—C1136.15 (16)C8—C11—H11C109.5
C4—C3—C2118.20 (16)H11A—C11—H11C109.5
C4—C3—H3120.9H11B—C11—H11C109.5
C2—C3—H3120.9C17—C12—C13121.80 (15)
C3—C4—C5119.95 (16)C17—C12—S1119.06 (12)
C3—C4—C9119.90 (17)C13—C12—S1119.14 (13)
C5—C4—C9120.15 (17)C14—C13—C12119.07 (16)
C6—C5—C4123.56 (16)C14—C13—H13120.5
C6—C5—H5118.2C12—C13—H13120.5
C4—C5—H5118.2C15—C14—C13120.09 (16)
C7—C6—C5114.31 (16)C15—C14—H14120.0
C7—C6—C10122.45 (17)C13—C14—H14120.0
C5—C6—C10123.24 (17)C16—C15—C14119.46 (16)
C6—C7—O1124.92 (16)C16—C15—H15120.3
C6—C7—C2124.52 (16)C14—C15—H15120.3
O1—C7—C2110.55 (14)C15—C16—C17122.10 (16)
C1—C8—O1110.49 (14)C15—C16—Cl1118.76 (13)
C1—C8—C11134.48 (17)C17—C16—Cl1119.14 (13)
O1—C8—C11115.03 (15)C16—C17—C12117.46 (15)
C4—C9—H9A109.5C16—C17—H17121.3
C4—C9—H9B109.5C12—C17—H17121.3
H9A—C9—H9B109.5
O2—S1—C1—C8−149.77 (15)C1—C2—C7—C6−179.53 (15)
O3—S1—C1—C8−17.69 (18)C3—C2—C7—O1179.81 (14)
C12—S1—C1—C896.71 (17)C1—C2—C7—O1−0.22 (18)
O2—S1—C1—C233.36 (16)C2—C1—C8—O1−0.38 (19)
O3—S1—C1—C2165.44 (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—C70.36 (18)S1—C1—C8—C113.0 (3)
S1—C1—C2—C7177.75 (12)C7—O1—C8—C10.25 (18)
C8—C1—C2—C3−179.68 (18)C7—O1—C8—C11179.72 (15)
S1—C1—C2—C3−2.3 (3)O2—S1—C12—C17−20.30 (15)
C7—C2—C3—C41.1 (2)O3—S1—C12—C17−150.40 (13)
C1—C2—C3—C4−178.86 (17)C1—S1—C12—C1793.83 (14)
C2—C3—C4—C5−1.6 (2)O2—S1—C12—C13159.90 (14)
C2—C3—C4—C9177.74 (16)O3—S1—C12—C1329.80 (16)
C3—C4—C5—C60.5 (3)C1—S1—C12—C13−85.96 (15)
C9—C4—C5—C6−178.82 (17)C17—C12—C13—C141.5 (3)
C4—C5—C6—C71.0 (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—O1179.26 (15)C13—C14—C15—C16−0.5 (3)
C10—C6—C7—O1−1.2 (3)C14—C15—C16—C171.2 (3)
C5—C6—C7—C2−1.5 (2)C14—C15—C16—Cl1−179.50 (15)
C10—C6—C7—C2178.05 (17)C15—C16—C17—C12−0.6 (3)
C8—O1—C7—C6179.31 (16)Cl1—C16—C17—C12−179.88 (13)
C8—O1—C7—C20.00 (18)C13—C12—C17—C16−0.8 (2)
C3—C2—C7—C60.5 (3)S1—C12—C17—C16179.45 (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···AD—HH···AD···AD—H···A
C14—H14···O3i0.952.603.264 (2)127
C10—H10A···Cg2ii0.982.863.704 (2)145
C10—H10C···Cg1ii0.983.083.536 (2)110
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC17H15ClO3S
Mr334.80
Crystal system, space groupMonoclinic, 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)
Z4
Radiation typeMo Kα
µ (mm−1)0.39
Crystal size (mm)0.36 × 0.29 × 0.25
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.872, 0.908
No. of measured, independent and
observed [I > 2σ(I)] reflections		14420, 3551, 3053
Rint0.028
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.105, 1.04
No. of reflections3551
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (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···AD—HH···AD···AD—H···A
C14—H14···O3i0.952.603.264 (2)127.4
C10—H10A···Cg2ii0.982.863.704 (2)144.9
C10—H10C···Cg1ii0.983.083.536 (2)109.7
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2.
 

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o794.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1813.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationSeo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3359.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o945
doi:10.1107/S1600536812008355
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