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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 o942
doi:10.1107/S1600536812008525

3-(3-Chloro­phenyl­sulfon­yl)-5-iso­propyl-2-methyl-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 26 February 2012; online 3 March 2012)

In the title compound, C18H17ClO3S, the 3-chloro­benzene ring makes a dihedral angle of 82.04 (5)° with the mean plane [r.m.s. 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.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1067.], 2011[Choi, H. D., Seo, P. J. & Lee, U. (2011). Acta Cryst. E67, o1226.]).

[Scheme 1]

Experimental

Crystal data

  • C18H17ClO3S

  • Mr = 348.83

  • Triclinic, [P \overline 1]

  • a = 7.1700 (2) Å

  • b = 9.9400 (2) Å

  • c = 12.2508 (3) Å

  • α = 83.484 (1)°

  • β = 77.907 (1)°

  • γ = 85.707 (1)°

  • V = 847.05 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.36 mm−1

  • T = 173 K

  • 0.29 × 0.24 × 0.13 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 = 0.903, Tmax = 0.955

  • 16044 measured reflections

  • 4231 independent reflections

  • 3596 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.132

  • S = 1.06

  • 4231 reflections

  • 211 parameters

  • H-atom parameters constrained

  • Δρmax = 0.85 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯O3i 0.95 2.42 3.321 (2) 159
C12—H12A⋯O2ii 0.98 2.42 3.375 (2) 165
C16—H16⋯Cgiii 0.95 2.71 3.646 (2) 170
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008525/lr2052sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008525/lr2052Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008525/lr2052Isup3.cml

checkCIF report


Comment top

As a part of our ongoing study of 5-isopropyl-2-methyl-1-benzofuran derivatives containing either 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) or 3-(4-chlorophenylsufonyl) (Choi 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 3-chlorobenzene ring and the mean plane of the benzofuran fragment is 82.04 (5)°. 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. 2 & Table 1, Cg 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. (2010, 2011).

Experimental top

77% 3-Chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-5-isopropyl-2-methyl-1-benzofuran (279 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8h, 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 70%, m.p. 357–358 K; Rf = 0.51 (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 diisopropyl ether 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 5-isopropyl-2-methyl-1-benzofuran derivatives containing either 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) or 3-(4-chlorophenylsufonyl) (Choi 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 3-chlorobenzene ring and the mean plane of the benzofuran fragment is 82.04 (5)°. 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. 2 & Table 1, Cg is the centroid of the C2–C7 benzene ring).

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 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. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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, y + 1, z; (ii) x + 1, y, z; (iii) - x + 1, - y + 1, - z + 1 (iv) x, y - 1, z; (v) x - 1, y, z.]
3-(3-Chlorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran top
Crystal data top
C18H17ClO3SZ = 2
Mr = 348.83F(000) = 364
Triclinic, P1Dx = 1.368 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1700 (2) ÅCell parameters from 7011 reflections
b = 9.9400 (2) Åθ = 2.6–28.4°
c = 12.2508 (3) ŵ = 0.36 mm−1
α = 83.484 (1)°T = 173 K
β = 77.907 (1)°Block, colourless
γ = 85.707 (1)°0.29 × 0.24 × 0.13 mm
V = 847.05 (4) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		4231 independent reflections
Radiation source: rotating anode3596 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.027
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 1.7°
φ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −13→13
Tmin = 0.903, Tmax = 0.955l = −16→16
16044 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)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.132H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0688P)2 + 0.4272P]
where P = (Fo2 + 2Fc2)/3
4231 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.85 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C18H17ClO3Sγ = 85.707 (1)°
Mr = 348.83V = 847.05 (4) Å3
Triclinic, P1Z = 2
a = 7.1700 (2) ÅMo Kα radiation
b = 9.9400 (2) ŵ = 0.36 mm−1
c = 12.2508 (3) ÅT = 173 K
α = 83.484 (1)°0.29 × 0.24 × 0.13 mm
β = 77.907 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		4231 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3596 reflections with I > 2σ(I)
Tmin = 0.903, Tmax = 0.955Rint = 0.027
16044 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.06Δρmax = 0.85 e Å−3
4231 reflectionsΔρmin = −0.46 e Å−3
211 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
Cl10.22055 (7)0.49026 (6)0.63396 (4)0.04596 (16)
S10.34765 (7)0.31464 (4)0.22246 (3)0.03083 (13)
O10.71701 (19)0.58220 (14)0.07545 (10)0.0376 (3)
O20.1494 (2)0.35118 (15)0.22738 (12)0.0418 (3)
O30.4313 (3)0.19619 (14)0.17075 (12)0.0470 (4)
C10.4757 (2)0.45364 (16)0.16032 (13)0.0269 (3)
C20.4074 (3)0.59381 (16)0.16760 (13)0.0287 (3)
C30.2339 (3)0.66147 (18)0.21091 (15)0.0350 (4)
H30.12630.61160.24710.042*
C40.2210 (3)0.8016 (2)0.20043 (17)0.0424 (5)
C50.3805 (4)0.8721 (2)0.14704 (18)0.0485 (5)
H50.37050.96840.14130.058*
C60.5538 (4)0.8085 (2)0.10175 (18)0.0476 (5)
H60.66070.85850.06450.057*
C70.5627 (3)0.66778 (19)0.11380 (14)0.0346 (4)
C80.6615 (3)0.45245 (18)0.10554 (14)0.0314 (4)
C90.0286 (4)0.8735 (2)0.2472 (2)0.0510 (5)
H9−0.07150.80550.25890.061*
C100.0305 (5)0.9199 (4)0.3600 (2)0.0800 (10)
H10A0.12770.98670.35130.120*
H10B0.06010.84190.41120.120*
H10C−0.09520.96120.39070.120*
C11−0.0257 (5)0.9892 (3)0.1681 (3)0.0735 (8)
H11A−0.15721.02230.19650.110*
H11B−0.01620.95820.09390.110*
H11C0.06081.06260.16220.110*
C120.8097 (3)0.3445 (2)0.07479 (18)0.0445 (5)
H12A0.89500.33380.12850.067*
H12B0.88360.3690−0.00080.067*
H12C0.74900.25900.07630.067*
C130.3857 (3)0.29535 (17)0.36169 (14)0.0301 (3)
C140.2933 (2)0.38686 (17)0.43515 (14)0.0300 (3)
H140.20600.45590.41270.036*
C150.3317 (3)0.3750 (2)0.54204 (14)0.0337 (4)
C160.4560 (3)0.2732 (2)0.57601 (17)0.0448 (5)
H160.48090.26610.64970.054*
C170.5430 (4)0.1826 (2)0.50199 (19)0.0509 (5)
H170.62680.11170.52540.061*
C180.5105 (3)0.1929 (2)0.39347 (17)0.0425 (4)
H180.57270.13090.34220.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0426 (3)0.0637 (3)0.0318 (2)−0.0110 (2)0.00138 (19)−0.0171 (2)
S10.0390 (2)0.0288 (2)0.0274 (2)−0.00753 (17)−0.00952 (17)−0.00579 (15)
O10.0365 (7)0.0478 (8)0.0290 (6)−0.0133 (6)−0.0028 (5)−0.0056 (6)
O20.0366 (7)0.0537 (8)0.0395 (7)−0.0132 (6)−0.0144 (6)−0.0029 (6)
O30.0747 (11)0.0293 (6)0.0396 (7)−0.0061 (7)−0.0112 (7)−0.0126 (6)
C10.0312 (8)0.0283 (7)0.0227 (7)−0.0026 (6)−0.0075 (6)−0.0047 (6)
C20.0369 (9)0.0279 (8)0.0223 (7)−0.0019 (7)−0.0080 (6)−0.0036 (6)
C30.0419 (10)0.0341 (9)0.0295 (8)0.0035 (7)−0.0087 (7)−0.0057 (7)
C40.0611 (13)0.0339 (9)0.0339 (9)0.0078 (9)−0.0154 (9)−0.0060 (7)
C50.0783 (16)0.0285 (9)0.0412 (11)0.0013 (10)−0.0184 (11)−0.0053 (8)
C60.0684 (15)0.0405 (10)0.0359 (10)−0.0230 (10)−0.0118 (10)0.0035 (8)
C70.0452 (10)0.0355 (9)0.0241 (8)−0.0089 (8)−0.0070 (7)−0.0032 (6)
C80.0336 (9)0.0399 (9)0.0230 (7)−0.0023 (7)−0.0084 (6)−0.0084 (7)
C90.0598 (14)0.0427 (11)0.0509 (12)0.0112 (10)−0.0137 (11)−0.0104 (9)
C100.0746 (19)0.110 (3)0.0598 (16)0.0405 (18)−0.0238 (15)−0.0397 (17)
C110.0756 (19)0.0659 (17)0.080 (2)0.0106 (15)−0.0291 (16)0.0048 (15)
C120.0342 (10)0.0599 (13)0.0421 (10)0.0094 (9)−0.0111 (8)−0.0176 (9)
C130.0352 (9)0.0282 (8)0.0275 (8)−0.0057 (7)−0.0076 (7)−0.0010 (6)
C140.0290 (8)0.0333 (8)0.0284 (8)−0.0054 (7)−0.0060 (6)−0.0035 (6)
C150.0316 (9)0.0432 (10)0.0258 (8)−0.0117 (7)−0.0018 (7)−0.0031 (7)
C160.0506 (12)0.0543 (12)0.0317 (9)−0.0072 (10)−0.0153 (9)0.0032 (8)
C170.0606 (14)0.0468 (12)0.0465 (12)0.0093 (10)−0.0224 (11)0.0039 (9)
C180.0513 (12)0.0353 (9)0.0404 (10)0.0065 (8)−0.0114 (9)−0.0040 (8)
Geometric parameters (Å, º) top
Cl1—C151.7307 (19)C9—C101.509 (4)
S1—O21.4308 (15)C9—H91.0000
S1—O31.4325 (14)C10—H10A0.9800
S1—C11.7290 (17)C10—H10B0.9800
S1—C131.7700 (18)C10—H10C0.9800
O1—C81.366 (2)C11—H11A0.9800
O1—C71.379 (2)C11—H11B0.9800
C1—C81.360 (2)C11—H11C0.9800
C1—C21.448 (2)C12—H12A0.9800
C2—C71.386 (3)C12—H12B0.9800
C2—C31.400 (2)C12—H12C0.9800
C3—C41.382 (3)C13—C181.382 (3)
C3—H30.9500C13—C141.386 (2)
C4—C51.389 (3)C14—C151.384 (2)
C4—C91.534 (3)C14—H140.9500
C5—C61.387 (3)C15—C161.385 (3)
C5—H50.9500C16—C171.374 (3)
C6—C71.387 (3)C16—H160.9500
C6—H60.9500C17—C181.388 (3)
C8—C121.475 (3)C17—H170.9500
C9—C111.501 (3)C18—H180.9500
O2—S1—O3119.69 (9)C9—C10—H10A109.5
O2—S1—C1107.76 (8)C9—C10—H10B109.5
O3—S1—C1109.52 (9)H10A—C10—H10B109.5
O2—S1—C13107.50 (8)C9—C10—H10C109.5
O3—S1—C13107.43 (9)H10A—C10—H10C109.5
C1—S1—C13103.79 (8)H10B—C10—H10C109.5
C8—O1—C7107.30 (14)C9—C11—H11A109.5
C8—C1—C2107.79 (15)C9—C11—H11B109.5
C8—C1—S1126.80 (14)H11A—C11—H11B109.5
C2—C1—S1125.15 (13)C9—C11—H11C109.5
C7—C2—C3119.77 (16)H11A—C11—H11C109.5
C7—C2—C1104.46 (16)H11B—C11—H11C109.5
C3—C2—C1135.75 (17)C8—C12—H12A109.5
C4—C3—C2119.30 (19)C8—C12—H12B109.5
C4—C3—H3120.3H12A—C12—H12B109.5
C2—C3—H3120.3C8—C12—H12C109.5
C3—C4—C5119.2 (2)H12A—C12—H12C109.5
C3—C4—C9118.4 (2)H12B—C12—H12C109.5
C5—C4—C9122.43 (19)C18—C13—C14121.69 (17)
C6—C5—C4123.05 (18)C18—C13—S1119.55 (14)
C6—C5—H5118.5C14—C13—S1118.73 (14)
C4—C5—H5118.5C15—C14—C13118.22 (17)
C7—C6—C5116.5 (2)C15—C14—H14120.9
C7—C6—H6121.8C13—C14—H14120.9
C5—C6—H6121.8C14—C15—C16121.22 (18)
O1—C7—C2110.48 (15)C14—C15—Cl1118.77 (15)
O1—C7—C6127.30 (18)C16—C15—Cl1120.01 (15)
C2—C7—C6122.21 (19)C17—C16—C15119.26 (19)
C1—C8—O1109.96 (15)C17—C16—H16120.4
C1—C8—C12134.29 (18)C15—C16—H16120.4
O1—C8—C12115.74 (16)C16—C17—C18121.1 (2)
C11—C9—C10111.0 (2)C16—C17—H17119.5
C11—C9—C4112.9 (2)C18—C17—H17119.5
C10—C9—C4110.2 (2)C13—C18—C17118.53 (19)
C11—C9—H9107.5C13—C18—H18120.7
C10—C9—H9107.5C17—C18—H18120.7
C4—C9—H9107.5
O2—S1—C1—C8−156.03 (15)S1—C1—C8—O1−175.31 (11)
O3—S1—C1—C8−24.32 (18)C2—C1—C8—C12178.02 (19)
C13—S1—C1—C890.16 (16)S1—C1—C8—C123.6 (3)
O2—S1—C1—C230.48 (16)C7—O1—C8—C10.90 (19)
O3—S1—C1—C2162.19 (14)C7—O1—C8—C12−178.25 (15)
C13—S1—C1—C2−83.33 (16)C3—C4—C9—C11−135.1 (2)
C8—C1—C2—C70.54 (18)C5—C4—C9—C1144.1 (3)
S1—C1—C2—C7175.07 (13)C3—C4—C9—C10100.2 (3)
C8—C1—C2—C3178.83 (19)C5—C4—C9—C10−80.7 (3)
S1—C1—C2—C3−6.6 (3)O2—S1—C13—C18141.75 (16)
C7—C2—C3—C4−0.7 (3)O3—S1—C13—C1811.71 (19)
C1—C2—C3—C4−178.83 (18)C1—S1—C13—C18−104.25 (17)
C2—C3—C4—C50.0 (3)O2—S1—C13—C14−40.32 (16)
C2—C3—C4—C9179.19 (17)O3—S1—C13—C14−170.36 (14)
C3—C4—C5—C60.9 (3)C1—S1—C13—C1473.68 (15)
C9—C4—C5—C6−178.2 (2)C18—C13—C14—C151.1 (3)
C4—C5—C6—C7−1.1 (3)S1—C13—C14—C15−176.74 (13)
C8—O1—C7—C2−0.54 (19)C13—C14—C15—C16−1.2 (3)
C8—O1—C7—C6−179.70 (19)C13—C14—C15—Cl1178.92 (13)
C3—C2—C7—O1−178.62 (15)C14—C15—C16—C170.1 (3)
C1—C2—C7—O10.00 (19)Cl1—C15—C16—C17−179.99 (17)
C3—C2—C7—C60.6 (3)C15—C16—C17—C181.0 (4)
C1—C2—C7—C6179.21 (17)C14—C13—C18—C170.0 (3)
C5—C6—C7—O1179.36 (18)S1—C13—C18—C17177.84 (17)
C5—C6—C7—C20.3 (3)C16—C17—C18—C13−1.1 (4)
C2—C1—C8—O1−0.90 (19)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.952.423.321 (2)159
C12—H12A···O2ii0.982.423.375 (2)165
C16—H16···Cgiii0.952.713.646 (2)170
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC18H17ClO3S
Mr348.83
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.1700 (2), 9.9400 (2), 12.2508 (3)
α, β, γ (°)83.484 (1), 77.907 (1), 85.707 (1)
V (Å3)847.05 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.36
Crystal size (mm)0.29 × 0.24 × 0.13
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.903, 0.955
No. of measured, independent and
observed [I > 2σ(I)] reflections		16044, 4231, 3596
Rint0.027
(sin θ/λ)max (Å−1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.132, 1.06
No. of reflections4231
No. of parameters211
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.85, −0.46

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 C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.952.423.321 (2)158.6
C12—H12A···O2ii0.982.423.375 (2)165.2
C16—H16···Cgiii0.952.713.646 (2)170.4
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (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. & Lee, U. (2011). Acta Cryst. E67, o1226.  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, o1067.  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 citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o942
doi:10.1107/S1600536812008525
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