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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Bioresmethrin: (5-benzyl­furan-3-yl)methyl 2,2-di­methyl-3-(2-methyl­prop-1-en-1-yl)cyclo­propane-1-carboxyl­ate

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: kmpark@gnu.ac.kr, jekim@gnu.ac.kr

(Received 25 September 2012; accepted 27 September 2012; online 3 October 2012)

In the title compound, C22H26O3, the dihedral angle between the cyclo­propane ring and the plane of the vinyl group is 88.2 (2)°. The dihedral angle between the phenyl and furan rings is 86.09 (8)°. In the crystal, weak inter­molecular C—H⋯π contacts together with very weak C—H⋯O hydrogen bonds stack the mol­ecules along the a axis.

Related literature

For information on the insecticidal activity of the title compound, see: Hill et al. (1993[Hill, A. S., McAdam, D. P., Edward, S. L. & Skerritt, J. H. (1993). J. Agric. Food Chem. 41, 2011-2018.]). For a related structure, see: Yang et al. (2011[Yang, H., Kim, T. H., Park, K.-M. & Kim, J. (2011). Acta Cryst. E67, o1275.]).

[Scheme 1]

Experimental

Crystal data
  • C22H26O3

  • Mr = 338.43

  • Monoclinic, P 21

  • a = 7.8438 (14) Å

  • b = 11.555 (2) Å

  • c = 10.9649 (18) Å

  • β = 108.375 (3)°

  • V = 943.2 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.33 × 0.28 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.992

  • 9877 measured reflections

  • 2458 independent reflections

  • 2156 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.096

  • S = 1.04

  • 2458 reflections

  • 230 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 phenyl ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7A⋯O3i 0.99 2.71 3.516 (3) 139
C11—H11⋯Cgii 0.95 2.63 3.559 (3) 167
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany..]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Bioresmethrin (systematic name: 5-benzyl-3-furylmethyl- 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate), is a synthetic pyrethroid with high insecticidal activity aganist a wide range of insect pests (Hill et al., 1993). However its crystal structure has not yet been reported.

In the title compound (Scheme 1, Fig. 1), the dihedral angle between the cyclopropane ring plane and the vinyl group plane is 88.2 (2)°. The dihedral angle between the benzene and furan ring planes in the benzylfuranyl group is 86.09 (8)°. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Yang et al., 2011).

In the crystal structure (Fig. 2) weak intermolecular C—H···π interactions [C11···Cgii 3.559 (4) Å. Cg is the centroid of the C1—C6 ring. (Symmetry codes: (ii) x - 1, y, z) are found together with very weak C7–H7A···O3 hydrogen bonds, Table 1, stack the molecules along a. These intermolecular interactions may contribute to the stabilization of the packing.

Related literature top

For information on the insecticidal activity of the title compound, see: Hill et al. (1993). For a related structure, see: Yang et al. (2011).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 1.00 Å, Uiso = 1.2Ueq(C) for methine C—H, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for Csp2—H and d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for CH3 groups. In the absence of significant anomalous scattering effects, Friedel pairs were merged. Because of this the absolute configuration of the title compound could not be reliably determined from the crystallographic data but has been suggested to be 5-benzyl-3-furylmethyl (1R,3R)- 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate from information provided by the manufacturers (the Dr. Ehrenstorfer GmbH Company). However, this cannot be confirmed by the present crystallographic determination.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing of the title compound with weak intermolecular C—H···π and C–H···O interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. (Symmetry codes: (i) x + 1, y, z; (ii) x - 1, y, z; (iii) x - 2, y, z - 1; (iv) x - 1, y, z - 1; (v) x, y, z - 1.
(5-Benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate top
Crystal data top
C22H26O3F(000) = 364
Mr = 338.43Dx = 1.192 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2685 reflections
a = 7.8438 (14) Åθ = 2.6–26.3°
b = 11.555 (2) ŵ = 0.08 mm1
c = 10.9649 (18) ÅT = 173 K
β = 108.375 (3)°Plate, colourless
V = 943.2 (3) Å30.33 × 0.28 × 0.10 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer
2458 independent reflections
Radiation source: fine-focus sealed tube2156 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ϕ and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.975, Tmax = 0.992k = 1515
9877 measured reflectionsl = 1314
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0305P)2 + 0.1943P]
where P = (Fo2 + 2Fc2)/3
2458 reflections(Δ/σ)max = 0.001
230 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.17 e Å3
Crystal data top
C22H26O3V = 943.2 (3) Å3
Mr = 338.43Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.8438 (14) ŵ = 0.08 mm1
b = 11.555 (2) ÅT = 173 K
c = 10.9649 (18) Å0.33 × 0.28 × 0.10 mm
β = 108.375 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
2458 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2156 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.992Rint = 0.058
9877 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.096H-atom parameters constrained
S = 1.04Δρmax = 0.20 e Å3
2458 reflectionsΔρmin = 0.17 e Å3
230 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O10.6817 (2)0.05992 (14)1.05641 (15)0.0323 (4)
O20.2777 (2)0.11355 (14)0.72431 (15)0.0326 (4)
O30.0111 (2)0.09696 (17)0.75770 (16)0.0393 (4)
C11.1967 (3)0.1520 (2)1.1670 (3)0.0378 (6)
H11.17750.23121.14300.045*
C21.3371 (4)0.1216 (3)1.2738 (3)0.0491 (7)
H21.41430.17971.32300.059*
C31.3657 (4)0.0084 (3)1.3093 (3)0.0531 (8)
H31.46300.01211.38300.064*
C41.2540 (4)0.0764 (3)1.2387 (3)0.0499 (7)
H41.27310.15521.26420.060*
C51.1138 (3)0.0463 (2)1.1306 (3)0.0363 (6)
H51.03810.10481.08100.044*
C61.0830 (3)0.0685 (2)1.0940 (2)0.0286 (5)
C70.9302 (3)0.1018 (2)0.9759 (2)0.0354 (5)
H7A0.96660.08620.89890.042*
H7B0.90870.18600.97870.042*
C80.7591 (3)0.03974 (19)0.9623 (2)0.0281 (5)
C90.6617 (3)0.03791 (19)0.8776 (2)0.0280 (5)
H90.68770.06740.80450.034*
C100.5105 (3)0.06772 (19)0.9187 (2)0.0274 (5)
C110.5305 (3)0.0060 (2)1.0258 (2)0.0320 (5)
H110.44920.00801.07420.038*
C120.3638 (3)0.1493 (2)0.8562 (2)0.0365 (6)
H12A0.27480.15010.90320.044*
H12B0.41280.22840.85810.044*
C130.1008 (3)0.08949 (18)0.6877 (2)0.0259 (4)
C140.0392 (3)0.05617 (17)0.5514 (2)0.0240 (4)
H140.13090.06440.50590.029*
C150.1023 (3)0.03703 (18)0.4976 (2)0.0255 (4)
C160.1542 (3)0.08798 (18)0.4709 (2)0.0244 (4)
H160.22950.12010.52140.029*
C170.0750 (3)0.1108 (2)0.3920 (2)0.0316 (5)
H17A0.00640.18020.42940.047*
H17B0.00870.06660.34540.047*
H17C0.19200.13370.33250.047*
C180.1790 (3)0.1031 (2)0.5866 (2)0.0347 (5)
H18A0.20540.04930.64740.052*
H18B0.09160.16080.63400.052*
H18C0.28990.14200.53630.052*
C190.1846 (3)0.14189 (19)0.3437 (2)0.0267 (4)
H190.12850.10570.28850.032*
C200.2821 (3)0.23548 (19)0.2982 (2)0.0276 (5)
C210.3813 (4)0.3044 (2)0.3695 (3)0.0390 (6)
H21A0.37440.26500.45010.058*
H21B0.50750.31200.31670.058*
H21C0.32730.38150.38850.058*
C220.2964 (4)0.2819 (2)0.1675 (2)0.0387 (6)
H22A0.23350.22990.12540.058*
H22B0.24170.35900.17620.058*
H22C0.42320.28710.11560.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0341 (8)0.0369 (9)0.0243 (9)0.0015 (7)0.0069 (7)0.0039 (7)
O20.0254 (8)0.0411 (9)0.0249 (9)0.0036 (7)0.0015 (7)0.0062 (7)
O30.0382 (9)0.0543 (11)0.0258 (9)0.0059 (8)0.0110 (8)0.0055 (8)
C10.0355 (13)0.0412 (13)0.0361 (15)0.0070 (11)0.0105 (12)0.0076 (11)
C20.0380 (15)0.073 (2)0.0338 (16)0.0106 (14)0.0083 (12)0.0147 (15)
C30.0280 (13)0.094 (3)0.0340 (17)0.0070 (15)0.0048 (12)0.0053 (16)
C40.0377 (14)0.0526 (17)0.0597 (19)0.0127 (13)0.0159 (14)0.0167 (15)
C50.0314 (12)0.0364 (12)0.0398 (15)0.0012 (10)0.0090 (11)0.0013 (11)
C60.0264 (10)0.0353 (11)0.0256 (12)0.0022 (9)0.0105 (9)0.0010 (10)
C70.0353 (12)0.0376 (12)0.0296 (13)0.0068 (10)0.0051 (10)0.0053 (10)
C80.0282 (11)0.0307 (11)0.0235 (12)0.0021 (9)0.0054 (9)0.0049 (9)
C90.0298 (11)0.0297 (11)0.0223 (12)0.0029 (9)0.0051 (9)0.0036 (9)
C100.0248 (10)0.0294 (11)0.0222 (12)0.0033 (8)0.0008 (9)0.0067 (9)
C110.0267 (11)0.0408 (13)0.0279 (13)0.0030 (9)0.0079 (10)0.0036 (10)
C120.0348 (13)0.0372 (13)0.0297 (14)0.0040 (10)0.0011 (11)0.0121 (11)
C130.0269 (10)0.0230 (9)0.0245 (11)0.0024 (8)0.0034 (9)0.0028 (9)
C140.0231 (10)0.0260 (10)0.0226 (11)0.0016 (8)0.0066 (9)0.0022 (8)
C150.0255 (10)0.0257 (10)0.0223 (11)0.0012 (8)0.0032 (9)0.0024 (9)
C160.0239 (10)0.0267 (10)0.0216 (11)0.0026 (8)0.0056 (8)0.0007 (9)
C170.0377 (13)0.0253 (10)0.0271 (13)0.0009 (9)0.0034 (10)0.0034 (9)
C180.0347 (12)0.0370 (12)0.0297 (13)0.0079 (10)0.0064 (10)0.0055 (10)
C190.0275 (10)0.0291 (10)0.0216 (11)0.0023 (8)0.0051 (9)0.0002 (9)
C200.0271 (11)0.0265 (10)0.0240 (12)0.0010 (8)0.0008 (9)0.0009 (9)
C210.0406 (13)0.0316 (12)0.0401 (15)0.0083 (10)0.0060 (12)0.0001 (11)
C220.0491 (15)0.0314 (12)0.0288 (14)0.0030 (11)0.0026 (11)0.0070 (10)
Geometric parameters (Å, º) top
O1—C111.360 (3)C12—H12B0.9900
O1—C81.372 (3)C13—C141.470 (3)
O2—C131.346 (3)C14—C151.525 (3)
O2—C121.450 (3)C14—C161.540 (3)
O3—C131.197 (3)C14—H141.0000
C1—C21.377 (4)C15—C161.504 (3)
C1—C61.385 (3)C15—C181.505 (3)
C1—H10.9500C15—C171.508 (3)
C2—C31.363 (5)C16—C191.476 (3)
C2—H20.9500C16—H161.0000
C3—C41.379 (5)C17—H17A0.9800
C3—H30.9500C17—H17B0.9800
C4—C51.383 (4)C17—H17C0.9800
C4—H40.9500C18—H18A0.9800
C5—C61.384 (3)C18—H18B0.9800
C5—H50.9500C18—H18C0.9800
C6—C71.511 (3)C19—C201.327 (3)
C7—C81.486 (3)C19—H190.9500
C7—H7A0.9900C20—C211.495 (3)
C7—H7B0.9900C20—C221.501 (3)
C8—C91.344 (3)C21—H21A0.9800
C9—C101.437 (3)C21—H21B0.9800
C9—H90.9500C21—H21C0.9800
C10—C111.340 (3)C22—H22A0.9800
C10—C121.478 (3)C22—H22B0.9800
C11—H110.9500C22—H22C0.9800
C12—H12A0.9900
C11—O1—C8106.11 (18)C13—C14—C16117.97 (17)
C13—O2—C12117.90 (18)C15—C14—C1658.78 (13)
C2—C1—C6120.7 (3)C13—C14—H14115.1
C2—C1—H1119.7C15—C14—H14115.1
C6—C1—H1119.7C16—C14—H14115.1
C3—C2—C1120.2 (3)C16—C15—C18118.33 (18)
C3—C2—H2119.9C16—C15—C17119.24 (19)
C1—C2—H2119.9C18—C15—C17113.2 (2)
C2—C3—C4120.2 (3)C16—C15—C1461.09 (14)
C2—C3—H3119.9C18—C15—C14119.90 (19)
C4—C3—H3119.9C17—C15—C14115.70 (18)
C3—C4—C5119.7 (3)C19—C16—C15122.87 (18)
C3—C4—H4120.2C19—C16—C14118.61 (17)
C5—C4—H4120.2C15—C16—C1460.13 (14)
C4—C5—C6120.5 (3)C19—C16—H16114.8
C4—C5—H5119.7C15—C16—H16114.8
C6—C5—H5119.7C14—C16—H16114.8
C5—C6—C1118.6 (2)C15—C17—H17A109.5
C5—C6—C7120.7 (2)C15—C17—H17B109.5
C1—C6—C7120.7 (2)H17A—C17—H17B109.5
C8—C7—C6114.2 (2)C15—C17—H17C109.5
C8—C7—H7A108.7H17A—C17—H17C109.5
C6—C7—H7A108.7H17B—C17—H17C109.5
C8—C7—H7B108.7C15—C18—H18A109.5
C6—C7—H7B108.7C15—C18—H18B109.5
H7A—C7—H7B107.6H18A—C18—H18B109.5
C9—C8—O1110.07 (19)C15—C18—H18C109.5
C9—C8—C7133.7 (2)H18A—C18—H18C109.5
O1—C8—C7116.2 (2)H18B—C18—H18C109.5
C8—C9—C10106.8 (2)C20—C19—C16127.0 (2)
C8—C9—H9126.6C20—C19—H19116.5
C10—C9—H9126.6C16—C19—H19116.5
C11—C10—C9105.50 (19)C19—C20—C21124.8 (2)
C11—C10—C12127.2 (2)C19—C20—C22120.7 (2)
C9—C10—C12127.3 (2)C21—C20—C22114.5 (2)
C10—C11—O1111.5 (2)C20—C21—H21A109.5
C10—C11—H11124.2C20—C21—H21B109.5
O1—C11—H11124.2H21A—C21—H21B109.5
O2—C12—C10109.31 (18)C20—C21—H21C109.5
O2—C12—H12A109.8H21A—C21—H21C109.5
C10—C12—H12A109.8H21B—C21—H21C109.5
O2—C12—H12B109.8C20—C22—H22A109.5
C10—C12—H12B109.8C20—C22—H22B109.5
H12A—C12—H12B108.3H22A—C22—H22B109.5
O3—C13—O2123.6 (2)C20—C22—H22C109.5
O3—C13—C14126.8 (2)H22A—C22—H22C109.5
O2—C13—C14109.55 (17)H22B—C22—H22C109.5
C13—C14—C15122.92 (18)
C6—C1—C2—C30.2 (4)C12—O2—C13—O30.7 (3)
C1—C2—C3—C40.2 (4)C12—O2—C13—C14179.52 (18)
C2—C3—C4—C50.8 (4)O3—C13—C14—C1537.8 (3)
C3—C4—C5—C61.1 (4)O2—C13—C14—C15143.42 (19)
C4—C5—C6—C10.8 (4)O3—C13—C14—C1631.4 (3)
C4—C5—C6—C7180.0 (2)O2—C13—C14—C16147.39 (18)
C2—C1—C6—C50.2 (3)C13—C14—C15—C16105.1 (2)
C2—C1—C6—C7179.3 (2)C13—C14—C15—C182.8 (3)
C5—C6—C7—C843.0 (3)C16—C14—C15—C18107.9 (2)
C1—C6—C7—C8137.8 (2)C13—C14—C15—C17144.2 (2)
C11—O1—C8—C91.3 (2)C16—C14—C15—C17110.7 (2)
C11—O1—C8—C7179.2 (2)C18—C15—C16—C19142.9 (2)
C6—C7—C8—C9113.6 (3)C17—C15—C16—C191.7 (3)
C6—C7—C8—O163.7 (3)C14—C15—C16—C19106.6 (2)
O1—C8—C9—C101.1 (2)C18—C15—C16—C14110.4 (2)
C7—C8—C9—C10178.5 (2)C17—C15—C16—C14105.0 (2)
C8—C9—C10—C110.5 (2)C13—C14—C16—C19133.0 (2)
C8—C9—C10—C12179.5 (2)C15—C14—C16—C19113.6 (2)
C9—C10—C11—O10.3 (2)C13—C14—C16—C15113.4 (2)
C12—C10—C11—O1179.7 (2)C15—C16—C19—C20156.9 (2)
C8—O1—C11—C101.0 (3)C14—C16—C19—C20131.9 (2)
C13—O2—C12—C10121.1 (2)C16—C19—C20—C210.2 (4)
C11—C10—C12—O2123.2 (2)C16—C19—C20—C22178.4 (2)
C9—C10—C12—O256.8 (3)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C7—H7A···O3i0.992.713.516 (3)139
C11—H11···Cgii0.952.633.559 (3)167
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC22H26O3
Mr338.43
Crystal system, space groupMonoclinic, P21
Temperature (K)173
a, b, c (Å)7.8438 (14), 11.555 (2), 10.9649 (18)
β (°) 108.375 (3)
V3)943.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.33 × 0.28 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.975, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
9877, 2458, 2156
Rint0.058
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.096, 1.04
No. of reflections2458
No. of parameters230
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.17

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C7—H7A···O3i0.992.713.516 (3)139
C11—H11···Cgii0.952.633.559 (3)167
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010–0009089).

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany..
First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHill, A. S., McAdam, D. P., Edward, S. L. & Skerritt, J. H. (1993). J. Agric. Food Chem. 41, 2011–2018.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationYang, H., Kim, T. H., Park, K.-M. & Kim, J. (2011). Acta Cryst. E67, o1275.  Web of Science CSD CrossRef IUCr Journals

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
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds