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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 7| July 2012| Page o2027
https://doi.org/10.1107/S1600536812024592

3-(4-Bromo­phenyl­sulfon­yl)-5-chloro-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 24 May 2012; accepted 30 May 2012; online 13 June 2012)

In the title compound, C15H10BrClO3S, the 4-bromo-substituted benzene ring forms a dihedral angle of 72.55 (6)° with the mean plane [mean deviation = 0.008 (2) Å] of the benzofuran ring system. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds into chains along [001]. There are also π–π inter­actions between the furan and benzene rings of symmetry-related benzofuran systems [centroid–centroid distances = 3.549 (3) and 3.632 (3) 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, o1190.], 2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2350.]).

[Scheme 1]

Experimental

Crystal data

  • C15H10BrClO3S

  • Mr = 385.65

  • Triclinic, [P \overline 1]

  • a = 7.1089 (2) Å

  • b = 10.4169 (3) Å

  • c = 11.0217 (3) Å

  • α = 69.659 (2)°

  • β = 89.526 (2)°

  • γ = 71.632 (1)°

  • V = 721.58 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.18 mm−1

  • T = 173 K

  • 0.38 × 0.31 × 0.27 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 = 0.448, Tmax = 0.746

  • 13182 measured reflections

  • 3570 independent reflections

  • 3007 reflections with I > 2σ(I)

  • Rint = 0.054
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.097

  • S = 1.08

  • 3570 reflections

  • 191 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11⋯O2i 0.95 2.53 3.203 (3) 128
C15—H15⋯O3ii 0.95 2.57 3.195 (3) 124
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+1, -y, -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: https://doi.org/10.1107/S1600536812024592/lh5482sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024592/lh5482Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024592/lh5482Isup3.cml

checkCIF report


Comment top

As a part of our ongoing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 3-phenylsulfonyl (Choi et al., 2008) and 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) 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 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromo substituted benzene ring and the mean plane of the benzofuran fragment is 72.55 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also exhibits offset π–π interactions between the furan and benzene rings of neighbouring molecules, with Cg1···Cg2iii & Cg1···Cg2iv distances of 3.549 (3) Å & 3.632 (3) Å [Symmetry codes: (iii) - x + 1,- y + 1,- z + 1; (iv) - x, - y + 1,- z + 1] and interplanar distances of 3.510 (3) Å & 3.343 (3) Å resulting in slippages of 0.511 (3) Å & 1.420 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively).

Related literature top

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

Experimental top

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-chloro-2-methyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (40 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 (benzene) to afford the title compound as a colorless solid [yield 76%, m.p. 454-456 K; Rf = 0.71 (benzene)]. 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.

Structure description top

As a part of our ongoing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 3-phenylsulfonyl (Choi et al., 2008) and 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) 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 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromo substituted benzene ring and the mean plane of the benzofuran fragment is 72.55 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also exhibits offset π–π interactions between the furan and benzene rings of neighbouring molecules, with Cg1···Cg2iii & Cg1···Cg2iv distances of 3.549 (3) Å & 3.632 (3) Å [Symmetry codes: (iii) - x + 1,- y + 1,- z + 1; (iv) - x, - y + 1,- z + 1] and interplanar distances of 3.510 (3) Å & 3.343 (3) Å resulting in slippages of 0.511 (3) Å & 1.420 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively).

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

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 packing of the title compound. H atoms non-participating in hydrogen-bonding are omitted for clarity. [Symmetry codes: (i) - x + 1, - y , - z + 2; (ii) - x + 1, - y , - z + 1].
[Figure 3] Fig. 3. A view of the π–π interactions (dotted lines) in the crystal packing of the title compound. All H atoms are omitted for clarity. [Symmetry codes: (iii) - x + 1,- y + 1,- z + 1; (iv) - x, - y + 1,- z + 1].
3-(4-Bromophenylsulfonyl)-5-chloro-2-methyl-1-benzofuran top
Crystal data top
C15H10BrClO3SZ = 2
Mr = 385.65F(000) = 384
Triclinic, P1Dx = 1.775 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1089 (2) ÅCell parameters from 7922 reflections
b = 10.4169 (3) Åθ = 2.5–28.3°
c = 11.0217 (3) ŵ = 3.18 mm−1
α = 69.659 (2)°T = 173 K
β = 89.526 (2)°Block, colourless
γ = 71.632 (1)°0.38 × 0.31 × 0.27 mm
V = 721.58 (4) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3570 independent reflections
Radiation source: rotating anode3007 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.054
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.0°
φ and ω scansh = −9→8
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −13→13
Tmin = 0.448, Tmax = 0.746l = −14→14
13182 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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.097H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.0238P]
where P = (Fo2 + 2Fc2)/3
3570 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C15H10BrClO3Sγ = 71.632 (1)°
Mr = 385.65V = 721.58 (4) Å3
Triclinic, P1Z = 2
a = 7.1089 (2) ÅMo Kα radiation
b = 10.4169 (3) ŵ = 3.18 mm−1
c = 11.0217 (3) ÅT = 173 K
α = 69.659 (2)°0.38 × 0.31 × 0.27 mm
β = 89.526 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3570 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3007 reflections with I > 2σ(I)
Tmin = 0.448, Tmax = 0.746Rint = 0.054
13182 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.08Δρmax = 0.45 e Å−3
3570 reflectionsΔρmin = −0.43 e Å−3
191 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
Br1−0.05797 (4)−0.23812 (2)0.82146 (3)0.03829 (11)
Cl10.31879 (13)0.47313 (9)0.12675 (7)0.0514 (2)
S10.53111 (8)0.13394 (6)0.70691 (5)0.02350 (14)
O10.1919 (2)0.53895 (17)0.62583 (18)0.0320 (4)
O20.6309 (3)0.10707 (19)0.83068 (17)0.0320 (4)
O30.6452 (2)0.10389 (17)0.60557 (16)0.0282 (4)
C10.3820 (3)0.3152 (2)0.6417 (2)0.0237 (4)
C20.3255 (3)0.4018 (2)0.5047 (2)0.0242 (5)
C30.3615 (4)0.3785 (3)0.3887 (2)0.0288 (5)
H30.43910.28630.38740.035*
C40.2782 (4)0.4967 (3)0.2754 (3)0.0345 (6)
C50.1640 (4)0.6333 (3)0.2737 (3)0.0406 (7)
H50.10980.71080.19290.049*
C60.1294 (4)0.6564 (3)0.3885 (3)0.0378 (7)
H60.05390.74910.38980.045*
C70.2097 (4)0.5387 (3)0.5014 (3)0.0293 (5)
C80.2974 (4)0.4014 (3)0.7101 (3)0.0297 (5)
C90.2938 (4)0.3784 (3)0.8495 (3)0.0400 (6)
H9A0.16130.37800.87440.060*
H9B0.32380.45680.86610.060*
H9C0.39400.28500.90080.060*
C100.3644 (3)0.0345 (2)0.7367 (2)0.0246 (5)
C110.2993 (4)−0.0064 (3)0.8589 (2)0.0333 (6)
H110.34250.02020.92520.040*
C120.1709 (4)−0.0863 (3)0.8835 (3)0.0364 (6)
H120.1249−0.11460.96670.044*
C130.1106 (4)−0.1243 (2)0.7867 (3)0.0291 (5)
C140.1743 (4)−0.0834 (3)0.6636 (2)0.0305 (5)
H140.1313−0.11050.59760.037*
C150.3008 (4)−0.0028 (3)0.6388 (2)0.0286 (5)
H150.34440.02720.55500.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03630 (17)0.02806 (14)0.0493 (2)−0.01477 (11)0.00645 (13)−0.00910 (12)
Cl10.0655 (5)0.0720 (5)0.0242 (3)−0.0428 (4)0.0035 (3)−0.0084 (3)
S10.0238 (3)0.0256 (3)0.0201 (3)−0.0069 (2)0.0006 (2)−0.0082 (2)
O10.0265 (9)0.0271 (8)0.0463 (11)−0.0081 (7)0.0063 (8)−0.0187 (8)
O20.0309 (9)0.0384 (9)0.0253 (9)−0.0116 (7)−0.0032 (7)−0.0097 (7)
O30.0263 (9)0.0290 (8)0.0267 (9)−0.0060 (7)0.0046 (7)−0.0101 (7)
C10.0205 (11)0.0259 (10)0.0255 (12)−0.0089 (9)0.0020 (9)−0.0092 (9)
C20.0192 (11)0.0253 (10)0.0294 (12)−0.0104 (9)0.0007 (9)−0.0088 (9)
C30.0286 (12)0.0300 (11)0.0274 (13)−0.0130 (10)0.0027 (10)−0.0071 (10)
C40.0331 (14)0.0455 (14)0.0267 (13)−0.0246 (11)0.0010 (11)−0.0051 (11)
C50.0333 (14)0.0357 (13)0.0408 (17)−0.0189 (11)−0.0064 (12)0.0071 (12)
C60.0244 (13)0.0228 (11)0.0604 (19)−0.0103 (9)−0.0014 (12)−0.0059 (12)
C70.0219 (11)0.0290 (11)0.0397 (14)−0.0129 (9)0.0030 (10)−0.0116 (10)
C80.0235 (12)0.0351 (12)0.0354 (14)−0.0120 (10)0.0042 (10)−0.0165 (11)
C90.0392 (15)0.0550 (16)0.0365 (15)−0.0181 (13)0.0100 (12)−0.0274 (13)
C100.0260 (12)0.0228 (10)0.0225 (11)−0.0069 (9)0.0015 (9)−0.0061 (9)
C110.0420 (15)0.0394 (13)0.0227 (12)−0.0190 (11)0.0048 (11)−0.0114 (11)
C120.0431 (15)0.0384 (13)0.0251 (13)−0.0182 (12)0.0050 (11)−0.0042 (11)
C130.0275 (12)0.0215 (10)0.0334 (13)−0.0065 (9)0.0051 (10)−0.0059 (9)
C140.0316 (13)0.0337 (12)0.0297 (13)−0.0111 (10)0.0020 (11)−0.0153 (10)
C150.0312 (13)0.0307 (11)0.0242 (12)−0.0097 (10)0.0057 (10)−0.0108 (10)
Geometric parameters (Å, º) top
Br1—C131.887 (2)C6—C71.374 (4)
Cl1—C41.748 (3)C6—H60.9500
S1—O21.4380 (18)C8—C91.472 (4)
S1—O31.4392 (17)C9—H9A0.9800
S1—C11.735 (2)C9—H9B0.9800
S1—C101.765 (2)C9—H9C0.9800
O1—C81.374 (3)C10—C111.387 (3)
O1—C71.378 (3)C10—C151.389 (3)
C1—C81.364 (3)C11—C121.385 (4)
C1—C21.446 (3)C11—H110.9500
C2—C31.389 (3)C12—C131.373 (4)
C2—C71.392 (3)C12—H120.9500
C3—C41.383 (4)C13—C141.393 (4)
C3—H30.9500C14—C151.378 (4)
C4—C51.392 (4)C14—H140.9500
C5—C61.375 (4)C15—H150.9500
C5—H50.9500
O2—S1—O3120.14 (11)C1—C8—O1110.0 (2)
O2—S1—C1108.61 (11)C1—C8—C9134.5 (2)
O3—S1—C1106.53 (10)O1—C8—C9115.6 (2)
O2—S1—C10107.53 (11)C8—C9—H9A109.5
O3—S1—C10107.70 (10)C8—C9—H9B109.5
C1—S1—C10105.43 (11)H9A—C9—H9B109.5
C8—O1—C7107.14 (17)C8—C9—H9C109.5
C8—C1—C2107.8 (2)H9A—C9—H9C109.5
C8—C1—S1126.30 (19)H9B—C9—H9C109.5
C2—C1—S1125.94 (17)C11—C10—C15120.7 (2)
C3—C2—C7119.6 (2)C11—C10—S1119.19 (19)
C3—C2—C1135.8 (2)C15—C10—S1120.08 (18)
C7—C2—C1104.6 (2)C12—C11—C10119.5 (2)
C4—C3—C2116.4 (2)C12—C11—H11120.3
C4—C3—H3121.8C10—C11—H11120.3
C2—C3—H3121.8C13—C12—C11119.5 (2)
C3—C4—C5123.4 (3)C13—C12—H12120.2
C3—C4—Cl1118.2 (2)C11—C12—H12120.2
C5—C4—Cl1118.4 (2)C12—C13—C14121.5 (2)
C6—C5—C4120.2 (2)C12—C13—Br1119.62 (19)
C6—C5—H5119.9C14—C13—Br1118.8 (2)
C4—C5—H5119.9C15—C14—C13118.9 (2)
C7—C6—C5116.6 (2)C15—C14—H14120.5
C7—C6—H6121.7C13—C14—H14120.5
C5—C6—H6121.7C14—C15—C10119.8 (2)
C6—C7—O1125.6 (2)C14—C15—H15120.1
C6—C7—C2123.9 (2)C10—C15—H15120.1
O1—C7—C2110.5 (2)
O2—S1—C1—C8−27.8 (2)C1—C2—C7—O1−0.6 (2)
O3—S1—C1—C8−158.5 (2)C2—C1—C8—O1−0.8 (3)
C10—S1—C1—C887.2 (2)S1—C1—C8—O1179.12 (16)
O2—S1—C1—C2152.06 (19)C2—C1—C8—C9178.4 (3)
O3—S1—C1—C221.3 (2)S1—C1—C8—C9−1.7 (4)
C10—S1—C1—C2−92.9 (2)C7—O1—C8—C10.4 (2)
C8—C1—C2—C3−179.8 (3)C7—O1—C8—C9−179.0 (2)
S1—C1—C2—C30.3 (4)O2—S1—C10—C1122.3 (2)
C8—C1—C2—C70.8 (2)O3—S1—C10—C11153.12 (19)
S1—C1—C2—C7−179.05 (17)C1—S1—C10—C11−93.4 (2)
C7—C2—C3—C40.4 (3)O2—S1—C10—C15−157.24 (19)
C1—C2—C3—C4−178.8 (2)O3—S1—C10—C15−26.4 (2)
C2—C3—C4—C50.1 (4)C1—S1—C10—C1587.0 (2)
C2—C3—C4—Cl1−179.96 (17)C15—C10—C11—C120.5 (4)
C3—C4—C5—C60.3 (4)S1—C10—C11—C12−179.0 (2)
Cl1—C4—C5—C6−179.7 (2)C10—C11—C12—C130.3 (4)
C4—C5—C6—C7−1.1 (4)C11—C12—C13—C14−0.5 (4)
C5—C6—C7—O1−179.8 (2)C11—C12—C13—Br1178.11 (19)
C5—C6—C7—C21.7 (4)C12—C13—C14—C150.0 (4)
C8—O1—C7—C6−178.5 (2)Br1—C13—C14—C15−178.66 (18)
C8—O1—C7—C20.2 (2)C13—C14—C15—C100.8 (4)
C3—C2—C7—C6−1.4 (4)C11—C10—C15—C14−1.1 (4)
C1—C2—C7—C6178.1 (2)S1—C10—C15—C14178.47 (18)
C3—C2—C7—O1179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O2i0.952.533.203 (3)128
C15—H15···O3ii0.952.573.195 (3)124
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC15H10BrClO3S
Mr385.65
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)7.1089 (2), 10.4169 (3), 11.0217 (3)
α, β, γ (°)69.659 (2), 89.526 (2), 71.632 (1)
V (Å3)721.58 (4)
Z2
Radiation typeMo Kα
µ (mm−1)3.18
Crystal size (mm)0.38 × 0.31 × 0.27
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.448, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		13182, 3570, 3007
Rint0.054
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.097, 1.08
No. of reflections3570
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.45, −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
D—H···AD—HH···AD···AD—H···A
C11—H11···O2i0.952.533.203 (3)127.8
C15—H15···O3ii0.952.573.195 (3)123.5
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −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, o1190.  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, o2350.  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.

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2027
https://doi.org/10.1107/S1600536812024592
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