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

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ISSN: 2056-9890

2,5,7-Tri­methyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzo­furan

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 2 May 2012; accepted 5 May 2012; online 16 May 2012)

In the title compound, C18H18O3S, the 4-methyl­phenyl ring makes a dihedral angle of 86.35 (3)° with the mean plane [mean deviation = 0.006 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits weak ππ inter­actions between the furan and benzene rings of neighbouring benzofuran systems [centroid–centroid distance = 3.685 (2), inter­planar distance = 3.572 (2) and slippage = 0.906 (2) Å].

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
  • C18H18O3S

  • Mr = 314.38

  • Monoclinic, P 21 /c

  • a = 9.7666 (2) Å

  • b = 19.4511 (5) Å

  • c = 8.2979 (2) Å

  • β = 98.541 (1)°

  • V = 1558.88 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 173 K

  • 0.41 × 0.39 × 0.20 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 = 0.916, Tmax = 0.958

  • 15446 measured reflections

  • 3868 independent reflections

  • 3258 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.04

  • 3868 reflections

  • 203 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10C⋯O3i 0.98 2.46 3.310 (2) 146
C9—H9CCg1ii 0.98 2.93 3.907 (2) 179
C10—H10BCg2iii 0.98 2.92 3.800 (2) 150
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+2, -y+1, -z+2; (iii) -x+1, -y+1, -z+1.

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


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 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the benzofuran fragment is 86.35 (3)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C—H···O and C—H···π interactions (Table 1). The crystal packing (Fig. 2) also exhibits weak π···π interactions between the furan and benzene rings of neighbouring benzofuran systems, with a Cg2···Cg3i distance of 3.685 (2) Å and an interplanar distance of 3.572 (2) Å resulting in a slippage of 0.906 (2) Å (Cg3 is the centroid of the C2–C7 benzene ring).

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

3-Chloroperoxybenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 2,5,7-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (338 mg, 1.2 mmol) in dichloromethane (30 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 (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 413–414 K; Rf = 0.48 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate 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. The positions of methyl hydrogens were optimized rotationally.

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 the atom numbering scheme. Displacement ellipsoids are 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, C—H···π and π···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 + 1, - z + 2; (ii) - x + 2, - y + 1, - z + 2; (iii) - x + 1, - y + 1, - z + 1.]
2,5,7-Trimethyl-3-(4-methylphenylsulfonyl)-1-benzofuran top
Crystal data top
C18H18O3SF(000) = 664
Mr = 314.38Dx = 1.340 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5168 reflections
a = 9.7666 (2) Åθ = 2.4–28.2°
b = 19.4511 (5) ŵ = 0.22 mm1
c = 8.2979 (2) ÅT = 173 K
β = 98.541 (1)°Block, colourless
V = 1558.88 (6) Å30.41 × 0.39 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
3868 independent reflections
Radiation source: rotating anode3258 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.030
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.1°
ϕ and ω scansh = 1312
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 2125
Tmin = 0.916, Tmax = 0.958l = 1110
15446 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)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.116H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.5651P]
where P = (Fo2 + 2Fc2)/3
3868 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C18H18O3SV = 1558.88 (6) Å3
Mr = 314.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.7666 (2) ŵ = 0.22 mm1
b = 19.4511 (5) ÅT = 173 K
c = 8.2979 (2) Å0.41 × 0.39 × 0.20 mm
β = 98.541 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3868 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3258 reflections with I > 2σ(I)
Tmin = 0.916, Tmax = 0.958Rint = 0.030
15446 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.04Δρmax = 0.30 e Å3
3868 reflectionsΔρmin = 0.43 e Å3
203 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
xyzUiso*/Ueq
S10.77821 (4)0.617621 (19)0.95912 (5)0.03124 (12)
O10.44316 (10)0.54239 (6)0.69953 (13)0.0335 (3)
O20.73376 (14)0.68604 (6)0.99116 (16)0.0445 (3)
O30.84855 (13)0.57685 (6)1.09059 (14)0.0401 (3)
C10.63766 (15)0.56994 (7)0.86672 (18)0.0281 (3)
C20.62873 (14)0.49571 (7)0.86149 (17)0.0259 (3)
C30.70807 (15)0.44093 (8)0.93316 (18)0.0295 (3)
H30.79070.44901.00670.035*
C40.66347 (16)0.37470 (8)0.8946 (2)0.0328 (3)
C50.54034 (16)0.36373 (8)0.7862 (2)0.0342 (3)
H50.51220.31770.76120.041*
C60.45823 (15)0.41655 (9)0.71436 (19)0.0321 (3)
C70.50737 (14)0.48180 (8)0.75612 (18)0.0276 (3)
C80.52485 (16)0.59479 (8)0.7677 (2)0.0329 (3)
C90.7482 (2)0.31384 (9)0.9655 (3)0.0463 (4)
H9A0.79370.29240.88060.069*
H9B0.68730.28031.00710.069*
H9C0.81850.32941.05470.069*
C100.32615 (17)0.40458 (11)0.5996 (2)0.0438 (4)
H10A0.31800.35570.57130.066*
H10B0.32730.43180.50030.066*
H10C0.24710.41850.65220.066*
C110.4770 (2)0.66466 (10)0.7171 (3)0.0498 (5)
H11A0.48700.67180.60260.075*
H11B0.53280.69870.78490.075*
H11C0.37950.66980.73050.075*
C120.88605 (15)0.62242 (7)0.80711 (18)0.0281 (3)
C151.04793 (16)0.62512 (9)0.55823 (19)0.0355 (4)
C160.97063 (16)0.68243 (9)0.5909 (2)0.0360 (4)
H160.97380.72280.52730.043*
C170.88939 (16)0.68161 (8)0.71428 (19)0.0323 (3)
H170.83690.72090.73500.039*
C181.1300 (2)0.62519 (11)0.4184 (2)0.0504 (5)
H18A1.07140.60890.31960.076*
H18B1.21020.59480.44390.076*
H18C1.16170.67200.40060.076*
C130.96346 (15)0.56489 (8)0.77825 (19)0.0317 (3)
H130.96090.52470.84260.038*
C141.04408 (16)0.56690 (8)0.6550 (2)0.0355 (3)
H141.09790.52790.63590.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0373 (2)0.0257 (2)0.0299 (2)0.00632 (14)0.00250 (15)0.00488 (14)
O10.0277 (5)0.0347 (6)0.0360 (6)0.0051 (4)0.0020 (4)0.0004 (5)
O20.0568 (7)0.0282 (6)0.0508 (7)0.0068 (5)0.0156 (6)0.0142 (5)
O30.0457 (6)0.0439 (7)0.0279 (6)0.0111 (5)0.0041 (5)0.0011 (5)
C10.0300 (7)0.0248 (7)0.0295 (7)0.0007 (5)0.0039 (6)0.0024 (6)
C20.0259 (6)0.0257 (7)0.0256 (7)0.0019 (5)0.0022 (5)0.0022 (5)
C30.0268 (6)0.0281 (7)0.0321 (8)0.0014 (5)0.0005 (5)0.0012 (6)
C40.0333 (7)0.0275 (8)0.0373 (8)0.0011 (6)0.0046 (6)0.0016 (6)
C50.0350 (8)0.0270 (7)0.0410 (9)0.0067 (6)0.0072 (6)0.0072 (6)
C60.0263 (7)0.0385 (9)0.0314 (8)0.0060 (6)0.0040 (6)0.0091 (6)
C70.0242 (6)0.0306 (7)0.0273 (7)0.0022 (5)0.0016 (5)0.0013 (6)
C80.0334 (7)0.0299 (8)0.0355 (8)0.0045 (6)0.0051 (6)0.0001 (6)
C90.0503 (10)0.0282 (9)0.0590 (12)0.0037 (7)0.0032 (8)0.0053 (8)
C100.0293 (7)0.0596 (11)0.0405 (9)0.0081 (7)0.0009 (7)0.0155 (8)
C110.0514 (10)0.0350 (9)0.0611 (12)0.0153 (8)0.0022 (9)0.0067 (9)
C120.0283 (7)0.0251 (7)0.0287 (7)0.0043 (5)0.0030 (5)0.0012 (6)
C150.0278 (7)0.0457 (9)0.0311 (8)0.0095 (6)0.0021 (6)0.0032 (7)
C160.0346 (8)0.0359 (8)0.0349 (8)0.0085 (6)0.0028 (6)0.0068 (7)
C170.0312 (7)0.0262 (7)0.0375 (8)0.0023 (6)0.0018 (6)0.0019 (6)
C180.0444 (10)0.0665 (13)0.0418 (10)0.0132 (9)0.0108 (8)0.0055 (9)
C130.0313 (7)0.0272 (7)0.0342 (8)0.0014 (5)0.0033 (6)0.0018 (6)
C140.0305 (7)0.0343 (8)0.0400 (9)0.0008 (6)0.0008 (6)0.0046 (7)
Geometric parameters (Å, º) top
S1—O21.4369 (12)C9—H9C0.9800
S1—O31.4382 (12)C10—H10A0.9800
S1—C11.7377 (15)C10—H10B0.9800
S1—C121.7617 (16)C10—H10C0.9800
O1—C81.3643 (19)C11—H11A0.9800
O1—C71.3840 (17)C11—H11B0.9800
C1—C81.361 (2)C11—H11C0.9800
C1—C21.447 (2)C12—C171.388 (2)
C2—C71.3909 (19)C12—C131.391 (2)
C2—C31.397 (2)C15—C141.392 (2)
C3—C41.382 (2)C15—C161.395 (2)
C3—H30.9500C15—C181.505 (2)
C4—C51.407 (2)C16—C171.385 (2)
C4—C91.513 (2)C16—H160.9500
C5—C61.383 (2)C17—H170.9500
C5—H50.9500C18—H18A0.9800
C6—C71.383 (2)C18—H18B0.9800
C6—C101.504 (2)C18—H18C0.9800
C8—C111.478 (2)C13—C141.381 (2)
C9—H9A0.9800C13—H130.9500
C9—H9B0.9800C14—H140.9500
O2—S1—O3119.59 (8)C6—C10—H10A109.5
O2—S1—C1109.59 (7)C6—C10—H10B109.5
O3—S1—C1107.30 (7)H10A—C10—H10B109.5
O2—S1—C12108.21 (7)C6—C10—H10C109.5
O3—S1—C12107.66 (7)H10A—C10—H10C109.5
C1—S1—C12103.27 (7)H10B—C10—H10C109.5
C8—O1—C7106.73 (11)C8—C11—H11A109.5
C8—C1—C2107.24 (13)C8—C11—H11B109.5
C8—C1—S1126.32 (12)H11A—C11—H11B109.5
C2—C1—S1125.87 (11)C8—C11—H11C109.5
C7—C2—C3119.08 (13)H11A—C11—H11C109.5
C7—C2—C1104.77 (12)H11B—C11—H11C109.5
C3—C2—C1136.15 (13)C17—C12—C13120.90 (15)
C4—C3—C2118.45 (13)C17—C12—S1120.47 (12)
C4—C3—H3120.8C13—C12—S1118.59 (11)
C2—C3—H3120.8C14—C15—C16118.43 (15)
C3—C4—C5119.97 (14)C14—C15—C18120.57 (16)
C3—C4—C9120.27 (15)C16—C15—C18120.97 (16)
C5—C4—C9119.75 (15)C17—C16—C15121.36 (15)
C6—C5—C4123.28 (14)C17—C16—H16119.3
C6—C5—H5118.4C15—C16—H16119.3
C4—C5—H5118.4C16—C17—C12118.87 (15)
C7—C6—C5114.61 (13)C16—C17—H17120.6
C7—C6—C10122.29 (16)C12—C17—H17120.6
C5—C6—C10123.10 (15)C15—C18—H18A109.5
C6—C7—O1125.01 (13)C15—C18—H18B109.5
C6—C7—C2124.59 (14)H18A—C18—H18B109.5
O1—C7—C2110.40 (13)C15—C18—H18C109.5
C1—C8—O1110.86 (13)H18A—C18—H18C109.5
C1—C8—C11133.75 (16)H18B—C18—H18C109.5
O1—C8—C11115.37 (14)C14—C13—C12119.27 (14)
C4—C9—H9A109.5C14—C13—H13120.4
C4—C9—H9B109.5C12—C13—H13120.4
H9A—C9—H9B109.5C13—C14—C15121.17 (15)
C4—C9—H9C109.5C13—C14—H14119.4
H9A—C9—H9C109.5C15—C14—H14119.4
H9B—C9—H9C109.5
O2—S1—C1—C830.29 (16)C1—C2—C7—C6179.59 (14)
O3—S1—C1—C8161.58 (14)C3—C2—C7—O1179.33 (13)
C12—S1—C1—C884.84 (15)C1—C2—C7—O10.47 (16)
O2—S1—C1—C2159.46 (13)C2—C1—C8—O10.35 (17)
O3—S1—C1—C228.17 (15)S1—C1—C8—O1172.09 (11)
C12—S1—C1—C285.40 (14)C2—C1—C8—C11177.50 (19)
C8—C1—C2—C70.08 (16)S1—C1—C8—C115.8 (3)
S1—C1—C2—C7171.71 (11)C7—O1—C8—C10.64 (17)
C8—C1—C2—C3179.68 (17)C7—O1—C8—C11177.64 (14)
S1—C1—C2—C38.5 (3)O2—S1—C12—C1714.89 (14)
C7—C2—C3—C40.8 (2)O3—S1—C12—C17145.45 (12)
C1—C2—C3—C4179.43 (16)C1—S1—C12—C17101.24 (13)
C2—C3—C4—C50.4 (2)O2—S1—C12—C13167.49 (12)
C2—C3—C4—C9178.24 (15)O3—S1—C12—C1336.93 (13)
C3—C4—C5—C60.4 (3)C1—S1—C12—C1376.38 (13)
C9—C4—C5—C6179.01 (16)C14—C15—C16—C171.3 (2)
C4—C5—C6—C70.6 (2)C18—C15—C16—C17176.77 (15)
C4—C5—C6—C10179.54 (16)C15—C16—C17—C120.3 (2)
C5—C6—C7—O1179.95 (14)C13—C12—C17—C160.5 (2)
C10—C6—C7—O10.1 (2)S1—C12—C17—C16177.10 (11)
C5—C6—C7—C20.1 (2)C17—C12—C13—C140.3 (2)
C10—C6—C7—C2179.97 (15)S1—C12—C13—C14177.35 (11)
C8—O1—C7—C6179.37 (15)C12—C13—C14—C150.7 (2)
C8—O1—C7—C20.69 (16)C16—C15—C14—C131.5 (2)
C3—C2—C7—C60.6 (2)C18—C15—C14—C13176.57 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C12–C17 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively
D—H···AD—HH···AD···AD—H···A
C10—H10C···O3i0.982.463.310 (2)146
C9—H9C···Cg1ii0.982.933.907 (2)179
C10—H10B···Cg2iii0.982.923.800 (2)150
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+2, y+1, z+2; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC18H18O3S
Mr314.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)9.7666 (2), 19.4511 (5), 8.2979 (2)
β (°) 98.541 (1)
V3)1558.88 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.41 × 0.39 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.916, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
15446, 3868, 3258
Rint0.030
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.116, 1.04
No. of reflections3868
No. of parameters203
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.43

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 C12–C17 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively
D—H···AD—HH···AD···AD—H···A
C10—H10C···O3i0.982.463.310 (2)145.5
C9—H9C···Cg1ii0.982.933.907 (2)178.7
C10—H10B···Cg2iii0.982.923.800 (2)149.8
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+2, y+1, z+2; (iii) x+1, y+1, z+1.
 

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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