Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Pages o1901-o1902
https://doi.org/10.1107/S1600536810025055

1,7-Di­methyl­penta­cyclo­[5.4.0.02,6.03,10.05,9]undecane-8,11-dione

Sai Kumar Chakka,a Oluseye K. Onajole,a Thavendran Govender,b Glenn E. M. Maguire,a* Hong Suc and Hendrik G. Krugera

aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, bSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa, and cSchool of Chemistry, University of Cape Town, South Africa
*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 18 June 2010; accepted 25 June 2010; online 3 July 2010)

The structure of the title compound, C13H14O2, a penta­cyclo­undecane cage derivative, exhibits unusual Csp3—Csp3 single-bond lengths ranging from 1.505 (3) to 1.607 (2) Å and strained bond angles as small as 88.7 (1)° and as large as 121.0 (2)°. In this meso compound, an inter­nal non-crystallographic mirror plane exists, bis­ecting the mol­ecule. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into an infinite spiral about a twofold screw axis along the [100] direction.

Related literature

For related literature and examples of PCU cage structures exhibiting C—C bond lengths that deviate from the norm, see: Flippen-Anderson et al. (1991[Flippen-Anderson, J. L., George, C., Gilardi, R., Zajac, W. W., Walters, T. R., Marchand, A., Dave, P. R. & Arney, B. E. (1991). Acta Cryst. C47, 813-817.]); Bott et al. (1998[Bott, S. G., Marchand, A. P., Alihodzic, S. & Kumar, K. A. (1998). J. Chem. Crystallogr. 28, 251-258.]); Linden et al. (2005[Linden, A., Romański, J., Mlostoń, G. & Heimgartner, H. (2005). Acta Cryst. C61, o221-o226.]); Kruger et al. (2006[Kruger, H. G., Rademeyer, M. & Ramdhani, R. (2006). Acta Cryst. E62, o268-o270.]). For the crystal packing of analogous PCU cage structures, see: Kruger et al. (2006[Kruger, H. G., Rademeyer, M. & Ramdhani, R. (2006). Acta Cryst. E62, o268-o270.]); Boyle et al. (2007a[Boyle, G. A., Govender, T., Karpoormath, R. & Kruger, H. G. (2007a). Acta Cryst. E63, o3977.],b[Boyle, G. A., Govender, T., Karpoormath, R. & Kruger, H. G. (2007b). Acta Cryst. E63, o4797.]). For the synthesis, see: Mehta et al. (1981[Mehta, G., Srikrishna, A., Reddy, A. V. & Nair, M. S. (1981). Tetrahedron, 37, 4543-4559.]). For hydrogen bonding, see: Desiraju et al. (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology. IUCr Monographs on Crystallography. Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data

  • C13H14O2

  • Mr = 202.24

  • Orthorhombic, P 21 21 21

  • a = 7.7914 (2) Å

  • b = 8.2149 (3) Å

  • c = 15.4830 (5) Å

  • V = 991.00 (5) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.72 mm−1

  • T = 173 K

  • 0.32 × 0.25 × 0.21 mm
Data collection

  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.702, Tmax = 0.753

  • 4922 measured reflections

  • 1055 independent reflections

  • 1044 reflections with I > 2σ(I)

  • Rint = 0.020
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.090

  • S = 1.06

  • 1055 reflections

  • 137 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Selected bond lengths (Å)

C1—C2 1.525 (3)
C1—C7 1.529 (2)
C2—C3 1.546 (2)
C2—C6 1.549 (2)
C3—C4 1.515 (3)
C3—C8 1.587 (2)
C4—C5 1.520 (2)
C5—C12 1.519 (2)
C5—C6 1.560 (2)
C5—C10 1.607 (2)
C6—C11 1.551 (3)
C7—C8 1.549 (2)
C7—C11 1.553 (3)
C8—C9 1.515 (3)
C9—C10 1.523 (3)
C10—C13 1.505 (3)
C10—C11 1.560 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O2i 1.00 2.58 3.303 (2) 129
C3—H3⋯O2ii 1.00 2.59 3.335 (2) 131
Symmetry codes: (i) x-1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

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: 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.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810025055/hb5509sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025055/hb5509Isup2.hkl

checkCIF report


Comment top

As part of an ongoing study of the crystal structures and chemical reactivity of polycyclic pentacycloundecane (PCU) cage derivatives, the structure of the title compound, (I), was obtained (Scheme 1). Although the compound is known (Mehta et al., 1981), its crystal structure has not been reported. Previous studies showed that PCU cage derivatives normally display C—C bond lengths which deviate from the expected value of 1.54 Å (see related literature). Similar phenomneon on the C—C bond lengths for this structure is observed, as the lengths of 17 Csp3—Csp3 single bonds range from 1.505 (3) Å to 1.607 (2) Å, with the bond between C10—C13 being the shortest, while that between C5—C10 is the longest (see Table 1). The labelling scheme and molecular structure is presented in Figure 1. The atoms C5, C6, C11 and C10 form a slightly irregular square with r.m.s. deviation of fitted atoms 0.0007 Å and is a very strained system. The tetrahedral bond angles around C10 are the most strained with the smallest angle of 88.7 (1)° (C5—C10—C11) and the biggest angle of 121.0 (2)° (C11—C10—C13), deviating from the ideal tetrahedral angle of 109.5°. Other selected carbon atoms, which define the cage conformation and which are coplanar with r.m.s. deviation of the fitted atoms smaller than 0.01 Å, are the following (with r.m.s. deviation of the fitted atoms in bracket): C10, C5, C4 and C9 (0.0034 Å); C4, C9, C8 and C3 (0.0010 Å); C3, C8, C7 and C2 (0.0019 Å); C2, C7, C11 and C6 (0.0004 Å). In the molecule of this meso compound an internal mirror plane exists, bisecting C1 and the middle points of bonds C8—C3, C11—C6 and C10—C5. We noted a number of weak hydrogen bonds of the type C—H···O=C presented in this structure (Desiraju et al., 1999) (see Table 2). The molecules form a infinite right-hand spiral about a two fold screw-axis along the [100] direction via hydrogen bond C3—H3···O2 (see Figure 2).

Related literature top

For related literature and examples of PCU cage structures exhibiting C—C bond lengths that deviate from the norm, see: Flippen-Anderson et al. (1991); Bott et al. (1998); Linden et al. (2005); Kruger et al. (2006). For the crystal packing of analogous PCU cage structures, see: Kruger et al. (2006); Boyle et al. (2007a,b). For the synthesis, see: Mehta et al. (1981). For hydrogen bonding, see: Desiraju et al. (1999).

Experimental top

In a 250 ml round-bottomed flask covered with tin foil was placed 2,3-dimethyl hydroquinone (4.00 g, 0.03 mmol), sodium chlorate (1.73 g, 0.01 mmol), 2% H2SO4 (36 ml) and 50 mg of vanadium pentoxide (catalyst). The mixture was stirred overnight, and the product, 2,3-dimethylbenzoquinone, was extracted with dichloromethane, dried over sodium sulfate, filtered and the filterate concentrated in vacuo to obtain 3.00 g (76%). To a vigorously stirring solution of the dried product (3.00 g, 0.02 mmol) in toluene (12 ml) cooled to 273 K, freshly cracked cyclopentadiene (1.67 g, 0.025 mmol) was added. The mixture was kept at 273 K for 4 h, after which the solution was allowed to attain ambient temperature over night. The solution was poured into an evaporating dish and placed in a fumehood to evaporate the toluene, yielding the adduct as a crude brown oil (4.20 g). Without further purification, the material was dissolved in ethyl acetate and exposed to sunlight until a clear solution was obtained (two weeks). The solvent was removed in vacuo to obtain a crude product, which was purified on silica gel, using a mobile phase of 6:4 hexane/ethyl acetate. The title compound was obtained as a pure white crystalline solid (3.20 g, 72%), mp 381–382 K. 1H NMR [CDCl3, 400 MHz]: δ = 0.99 (s, 6 H, CH3), 1.85 (d, 1 H, J= 11.2 Hz, CH2), 1.99 (d, 1 H, J= 11.1 Hz, CH2), 2.68 (s, 2 H, CH), 2.73 (s, 2 H, CH), 2.81 (s, 2 H, CH). 13C NMR [CDCl3, 100 MHz]: δ = 11.4 (q), 41.1 (t), 43.3 (d), 44.2 (d), 54.7 (d), 213.8 (s). IR (ATR): 2958, 1741, 1453,1282, 1073, 1023, 903, 869, 660 and 457 cm-1. Colourless prisms of (I) were grown by slow evaporation of a solution of the title compound in methanol, at ambient temperature. The synthesis is summarised in Fig. 3.

Refinement top

The locations of the hydrogen atoms were found in a difference map and then positioned geometrically and allowed to ride on their respective parent atoms, with C—H bond lengths of 1.00 (CH), 0.99 (CH2), or 0.98 (CH3). They were then refined with a riding model with Uiso(H) = 1.5Ueq(CH3) and Uiso(H) = 1.2Ueq(X) for X = CH or CH2. When the data were unmerged, the Flack absolute structure parameter refined to -0.07 with s.u. 0.25. Because of the large s.u., in the final refinement, the Friedel pairs were merged.

Structure description top

As part of an ongoing study of the crystal structures and chemical reactivity of polycyclic pentacycloundecane (PCU) cage derivatives, the structure of the title compound, (I), was obtained (Scheme 1). Although the compound is known (Mehta et al., 1981), its crystal structure has not been reported. Previous studies showed that PCU cage derivatives normally display C—C bond lengths which deviate from the expected value of 1.54 Å (see related literature). Similar phenomneon on the C—C bond lengths for this structure is observed, as the lengths of 17 Csp3—Csp3 single bonds range from 1.505 (3) Å to 1.607 (2) Å, with the bond between C10—C13 being the shortest, while that between C5—C10 is the longest (see Table 1). The labelling scheme and molecular structure is presented in Figure 1. The atoms C5, C6, C11 and C10 form a slightly irregular square with r.m.s. deviation of fitted atoms 0.0007 Å and is a very strained system. The tetrahedral bond angles around C10 are the most strained with the smallest angle of 88.7 (1)° (C5—C10—C11) and the biggest angle of 121.0 (2)° (C11—C10—C13), deviating from the ideal tetrahedral angle of 109.5°. Other selected carbon atoms, which define the cage conformation and which are coplanar with r.m.s. deviation of the fitted atoms smaller than 0.01 Å, are the following (with r.m.s. deviation of the fitted atoms in bracket): C10, C5, C4 and C9 (0.0034 Å); C4, C9, C8 and C3 (0.0010 Å); C3, C8, C7 and C2 (0.0019 Å); C2, C7, C11 and C6 (0.0004 Å). In the molecule of this meso compound an internal mirror plane exists, bisecting C1 and the middle points of bonds C8—C3, C11—C6 and C10—C5. We noted a number of weak hydrogen bonds of the type C—H···O=C presented in this structure (Desiraju et al., 1999) (see Table 2). The molecules form a infinite right-hand spiral about a two fold screw-axis along the [100] direction via hydrogen bond C3—H3···O2 (see Figure 2).

For related literature and examples of PCU cage structures exhibiting C—C bond lengths that deviate from the norm, see: Flippen-Anderson et al. (1991); Bott et al. (1998); Linden et al. (2005); Kruger et al. (2006). For the crystal packing of analogous PCU cage structures, see: Kruger et al. (2006); Boyle et al. (2007a,b). For the synthesis, see: Mehta et al. (1981). For hydrogen bonding, see: Desiraju et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) with non-H atoms drawn with 40% probability displacement ellipsoids and H atoms are shown as open circles.
[Figure 2] Fig. 2. Projection viewed down the b axis of (I) showing the spirals up along the 2-fold screw axis in the [100] direction. Both the weak hydrogen bonds C3—H3···O2 and C2—H2···O2 are shown as dotted lines. All hydrogen atoms except H2 and H3 are omitted for clarity.
[Figure 3] Fig. 3. Preparation scheme for (I)
1,7-Dimethylpentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione top
Crystal data top
C13H14O2Dx = 1.356 Mg m−3
Mr = 202.24Melting point: 382 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2abCell parameters from 4922 reflections
a = 7.7914 (2) Åθ = 5.7–68.4°
b = 8.2149 (3) ŵ = 0.72 mm−1
c = 15.4830 (5) ÅT = 173 K
V = 991.00 (5) Å3Prism, colourless
Z = 40.32 × 0.25 × 0.21 mm
F(000) = 432
Data collection top
Bruker Kappa DUO APEXII
diffractometer		1055 independent reflections
Radiation source: fine-focus sealed tube1044 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
0.5° φ scans and ω scansθmax = 68.4°, θmin = 5.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		h = −9→9
Tmin = 0.702, Tmax = 0.753k = −9→9
4922 measured reflectionsl = −18→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0627P)2 + 0.1901P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1055 reflectionsΔρmax = 0.21 e Å−3
137 parametersΔρmin = −0.18 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0178 (18)
Primary atom site location: structure-invariant direct methods
Crystal data top
C13H14O2V = 991.00 (5) Å3
Mr = 202.24Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.7914 (2) ŵ = 0.72 mm−1
b = 8.2149 (3) ÅT = 173 K
c = 15.4830 (5) Å0.32 × 0.25 × 0.21 mm
Data collection top
Bruker Kappa DUO APEXII
diffractometer		1055 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)		1044 reflections with I > 2σ(I)
Tmin = 0.702, Tmax = 0.753Rint = 0.020
4922 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.06Δρmax = 0.21 e Å−3
1055 reflectionsΔρmin = −0.18 e Å−3
137 parameters
Special details top

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 30 mm; combination of φ and ω scans of 0.5°, 40 s per °, 2 iterations.

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
O10.7584 (2)0.32372 (19)0.54950 (9)0.0395 (4)
C10.4669 (2)0.6969 (2)0.36778 (12)0.0255 (4)
H1A0.43950.79120.40510.031*
H1B0.38580.69150.31870.031*
O21.05692 (19)0.5921 (2)0.41443 (11)0.0381 (4)
C20.4768 (2)0.5374 (2)0.41804 (11)0.0233 (4)
H20.36740.50190.44610.028*
C30.6306 (2)0.5612 (2)0.47985 (11)0.0232 (4)
H30.59880.60880.53710.028*
C40.7082 (2)0.3924 (2)0.48546 (12)0.0251 (4)
C50.7092 (2)0.3279 (2)0.39345 (12)0.0229 (4)
C60.5531 (2)0.4167 (2)0.35149 (12)0.0231 (4)
H60.46970.34740.31900.028*
C70.6546 (2)0.6948 (2)0.33893 (11)0.0224 (4)
H70.69120.78890.30230.027*
C80.7553 (2)0.6726 (2)0.42436 (12)0.0229 (4)
H80.78720.77720.45320.027*
C90.9079 (2)0.5714 (2)0.39604 (12)0.0248 (4)
C100.8361 (2)0.4397 (2)0.33708 (11)0.0231 (4)
C110.6756 (2)0.5243 (2)0.29697 (11)0.0230 (4)
H110.66300.51810.23280.028*
C120.7267 (3)0.1443 (2)0.38573 (13)0.0316 (5)
H12A0.72600.11330.32460.047*
H12B0.63060.09150.41540.047*
H12C0.83500.10960.41220.047*
C130.9672 (3)0.3567 (3)0.28080 (13)0.0334 (5)
H13A0.91040.27400.24520.050*
H13B1.05410.30460.31720.050*
H13C1.02230.43740.24330.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0546 (10)0.0372 (8)0.0267 (7)0.0111 (8)−0.0061 (7)0.0058 (6)
C10.0229 (9)0.0265 (9)0.0269 (9)0.0046 (7)−0.0001 (7)0.0022 (8)
O20.0216 (7)0.0364 (8)0.0564 (10)−0.0003 (6)−0.0065 (7)−0.0079 (7)
C20.0193 (8)0.0247 (9)0.0259 (8)0.0007 (7)0.0027 (7)0.0016 (7)
C30.0255 (8)0.0245 (9)0.0195 (8)0.0020 (8)0.0024 (7)−0.0010 (7)
C40.0250 (8)0.0264 (9)0.0240 (8)0.0009 (8)0.0010 (7)0.0017 (7)
C50.0237 (9)0.0195 (9)0.0256 (9)−0.0004 (7)0.0012 (7)−0.0011 (7)
C60.0218 (8)0.0240 (9)0.0235 (8)−0.0016 (8)−0.0017 (7)−0.0019 (7)
C70.0231 (9)0.0208 (8)0.0232 (8)−0.0001 (8)−0.0001 (7)0.0032 (7)
C80.0227 (8)0.0201 (8)0.0257 (9)−0.0009 (8)−0.0029 (8)−0.0014 (7)
C90.0224 (9)0.0241 (9)0.0280 (9)−0.0012 (8)0.0004 (7)0.0030 (7)
C100.0215 (9)0.0240 (9)0.0237 (8)0.0016 (8)0.0023 (7)−0.0003 (7)
C110.0236 (9)0.0255 (9)0.0200 (8)0.0001 (8)−0.0001 (7)−0.0013 (7)
C120.0421 (11)0.0204 (9)0.0324 (9)0.0009 (9)0.0015 (9)−0.0011 (7)
C130.0315 (11)0.0344 (11)0.0344 (9)0.0057 (9)0.0092 (9)−0.0020 (9)
Geometric parameters (Å, º) top
O1—C41.206 (2)C6—H61.0000
C1—C21.525 (3)C7—C81.549 (2)
C1—C71.529 (2)C7—C111.553 (3)
C1—H1A0.9900C7—H71.0000
C1—H1B0.9900C8—C91.515 (3)
O2—C91.207 (3)C8—H81.0000
C2—C31.546 (2)C9—C101.523 (3)
C2—C61.549 (2)C10—C131.505 (3)
C2—H21.0000C10—C111.560 (2)
C3—C41.515 (3)C11—H111.0000
C3—C81.587 (2)C12—H12A0.9800
C3—H31.0000C12—H12B0.9800
C4—C51.520 (2)C12—H12C0.9800
C5—C121.519 (2)C13—H13A0.9800
C5—C61.560 (2)C13—H13B0.9800
C5—C101.607 (2)C13—H13C0.9800
C6—C111.551 (3)
C2—C1—C795.26 (14)C1—C7—H7115.5
C2—C1—H1A112.7C8—C7—H7115.5
C7—C1—H1A112.7C11—C7—H7115.5
C2—C1—H1B112.7C9—C8—C7102.44 (14)
C7—C1—H1B112.7C9—C8—C3108.72 (15)
H1A—C1—H1B110.2C7—C8—C3102.71 (14)
C1—C2—C3104.26 (15)C9—C8—H8113.9
C1—C2—C6103.29 (14)C7—C8—H8113.9
C3—C2—C6101.25 (14)C3—C8—H8113.9
C1—C2—H2115.4O2—C9—C8127.53 (19)
C3—C2—H2115.4O2—C9—C10126.49 (19)
C6—C2—H2115.4C8—C9—C10105.96 (15)
C4—C3—C2103.24 (14)C13—C10—C9114.82 (16)
C4—C3—C8108.33 (14)C13—C10—C11121.02 (15)
C2—C3—C8102.26 (13)C9—C10—C11102.51 (14)
C4—C3—H3114.0C13—C10—C5118.23 (16)
C2—C3—H3114.0C9—C10—C5107.86 (14)
C8—C3—H3114.0C11—C10—C588.69 (13)
O1—C4—C3127.20 (18)C6—C11—C7102.81 (13)
O1—C4—C5127.29 (18)C6—C11—C1091.31 (13)
C3—C4—C5105.51 (15)C7—C11—C10108.66 (14)
C12—C5—C4114.86 (16)C6—C11—H11116.8
C12—C5—C6120.11 (16)C7—C11—H11116.8
C4—C5—C6102.91 (15)C10—C11—H11116.8
C12—C5—C10117.97 (16)C5—C12—H12A109.5
C4—C5—C10108.24 (14)C5—C12—H12B109.5
C6—C5—C1089.23 (13)H12A—C12—H12B109.5
C2—C6—C11103.48 (14)C5—C12—H12C109.5
C2—C6—C5108.76 (14)H12A—C12—H12C109.5
C11—C6—C590.77 (13)H12B—C12—H12C109.5
C2—C6—H6116.8C10—C13—H13A109.5
C11—C6—H6116.8C10—C13—H13B109.5
C5—C6—H6116.8H13A—C13—H13B109.5
C1—C7—C8103.67 (14)C10—C13—H13C109.5
C1—C7—C11103.47 (15)H13A—C13—H13C109.5
C8—C7—C11101.38 (14)H13B—C13—H13C109.5
C7—C1—C2—C352.94 (15)C2—C3—C8—C7−0.35 (17)
C7—C1—C2—C6−52.54 (16)C7—C8—C9—O2134.3 (2)
C1—C2—C3—C4−145.63 (14)C3—C8—C9—O2−117.5 (2)
C6—C2—C3—C4−38.63 (17)C7—C8—C9—C10−44.16 (18)
C1—C2—C3—C8−33.19 (16)C3—C8—C9—C1064.06 (18)
C6—C2—C3—C873.81 (15)O2—C9—C10—C13−15.9 (3)
C2—C3—C4—O1−136.5 (2)C8—C9—C10—C13162.55 (16)
C8—C3—C4—O1115.6 (2)O2—C9—C10—C11−149.1 (2)
C2—C3—C4—C543.41 (18)C8—C9—C10—C1129.38 (17)
C8—C3—C4—C5−64.51 (17)O2—C9—C10—C5118.2 (2)
O1—C4—C5—C1218.7 (3)C8—C9—C10—C5−63.30 (18)
C3—C4—C5—C12−161.21 (16)C12—C5—C10—C13−0.9 (3)
O1—C4—C5—C6151.1 (2)C4—C5—C10—C13131.62 (18)
C3—C4—C5—C6−28.88 (18)C6—C5—C10—C13−125.04 (17)
O1—C4—C5—C10−115.4 (2)C12—C5—C10—C9−133.26 (18)
C3—C4—C5—C1064.62 (18)C4—C5—C10—C9−0.7 (2)
C1—C2—C6—C1133.43 (17)C6—C5—C10—C9102.62 (16)
C3—C2—C6—C11−74.33 (16)C12—C5—C10—C11124.02 (18)
C1—C2—C6—C5128.94 (15)C4—C5—C10—C11−103.44 (15)
C3—C2—C6—C521.18 (17)C6—C5—C10—C11−0.10 (12)
C12—C5—C6—C2133.27 (18)C2—C6—C11—C7−0.07 (17)
C4—C5—C6—C24.12 (18)C5—C6—C11—C7−109.58 (14)
C10—C5—C6—C2−104.42 (15)C2—C6—C11—C10109.40 (14)
C12—C5—C6—C11−122.20 (18)C5—C6—C11—C10−0.10 (12)
C4—C5—C6—C11108.64 (14)C1—C7—C11—C6−33.26 (17)
C10—C5—C6—C110.10 (12)C8—C7—C11—C673.97 (16)
C2—C1—C7—C8−52.87 (16)C1—C7—C11—C10−129.09 (15)
C2—C1—C7—C1152.62 (15)C8—C7—C11—C10−21.86 (17)
C1—C7—C8—C9146.37 (15)C13—C10—C11—C6122.67 (18)
C11—C7—C8—C939.30 (17)C9—C10—C11—C6−107.91 (14)
C1—C7—C8—C333.62 (18)C5—C10—C11—C60.10 (12)
C11—C7—C8—C3−73.44 (16)C13—C10—C11—C7−133.34 (17)
C4—C3—C8—C90.2 (2)C9—C10—C11—C7−3.91 (17)
C2—C3—C8—C9−108.38 (15)C5—C10—C11—C7104.10 (14)
C4—C3—C8—C7108.24 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i1.002.583.303 (2)129
C3—H3···O2ii1.002.593.335 (2)131
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formulaC13H14O2
Mr202.24
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)7.7914 (2), 8.2149 (3), 15.4830 (5)
V (Å3)991.00 (5)
Z4
Radiation typeCu Kα
µ (mm−1)0.72
Crystal size (mm)0.32 × 0.25 × 0.21
Data collection
DiffractometerBruker Kappa DUO APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.702, 0.753
No. of measured, independent and
observed [I > 2σ(I)] reflections		4922, 1055, 1044
Rint0.020
(sin θ/λ)max (Å−1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.090, 1.06
No. of reflections1055
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.18

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXL97 (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Selected bond lengths (Å) top
C1—C21.525 (3)C5—C101.607 (2)
C1—C71.529 (2)C6—C111.551 (3)
C2—C31.546 (2)C7—C81.549 (2)
C2—C61.549 (2)C7—C111.553 (3)
C3—C41.515 (3)C8—C91.515 (3)
C3—C81.587 (2)C9—C101.523 (3)
C4—C51.520 (2)C10—C131.505 (3)
C5—C121.519 (2)C10—C111.560 (2)
C5—C61.560 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i1.002.583.303 (2)129
C3—H3···O2ii1.002.593.335 (2)131
Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+1.
 

Acknowledgements

This work was supported by grants from the National Research Foundation (South Africa), GUN 2046819, and the University of KwaZulu-Natal.

References

First citationBott, S. G., Marchand, A. P., Alihodzic, S. & Kumar, K. A. (1998). J. Chem. Crystallogr. 28, 251–258.  Web of Science CSD CrossRef CAS Google Scholar
 First citationBoyle, G. A., Govender, T., Karpoormath, R. & Kruger, H. G. (2007a). Acta Cryst. E63, o3977.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBoyle, G. A., Govender, T., Karpoormath, R. & Kruger, H. G. (2007b). Acta Cryst. E63, o4797.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDesiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology. IUCr Monographs on Crystallography. Oxford University Press.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFlippen-Anderson, J. L., George, C., Gilardi, R., Zajac, W. W., Walters, T. R., Marchand, A., Dave, P. R. & Arney, B. E. (1991). Acta Cryst. C47, 813–817.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationKruger, H. G., Rademeyer, M. & Ramdhani, R. (2006). Acta Cryst. E62, o268–o270.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLinden, A., Romański, J., Mlostoń, G. & Heimgartner, H. (2005). Acta Cryst. C61, o221–o226.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMehta, G., Srikrishna, A., Reddy, A. V. & Nair, M. S. (1981). Tetrahedron, 37, 4543–4559.  CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.  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
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Pages o1901-o1902
https://doi.org/10.1107/S1600536810025055
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS