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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 67| Part 12| December 2011| Page o3334
https://doi.org/10.1107/S1600536811047854

1,3-Bis(propan-2-yl)naphthalene

Bernd Schröder,a Ligia Rebelo Gomesb and John Nicolson Lowc*

aCICECO, Departamento de Química, Faculdade de Ciências, Universidade do Aveiro, 3810-193 Aveiro, Portugal, bCIAGEB-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal, and cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland.
*Correspondence e-mail: jnlow111@gmail.com

(Received 9 November 2011; accepted 10 November 2011; online 16 November 2011)

In the title compound, C16H20, one of the isopropyl groups shows almost equal displacements [1.252 (1) and −1.270 (1) Å] of its methyl-C atoms from the mean plane of the naphthalene ring system, while the other shows asymmetric displacements [1.586 (2) and −0.315 (1) Å]. In the crystal, the mol­ecules are linked into sheets lying in the ab plane by three C—H⋯π contacts, two involving donors belonging to the isopropyl groups and the third a donor atom from the naphthalene ring system. The different orientations of the isopropyl groups might be attributed to the fact that the C—H⋯π inter­action involving one of them is enhanced by the C—H⋯π inter­action involving the aromatic ring.

Related literature

For background to diisopropyl­naphthalenes, see: Addison (1983[Addison, R. F. (1983). Environ. Sci. Technol. 17, 486A-494A.]); Brzozowski et al. (2001[Brzozowski, R., Dobrowolski, J. C., Jamróz, M. H. & Skupiński, W. (2001). J. Mol. Catal. A, 170, 95-99.]); Collin et al. (2003[Collin, G., Höke, H. & Greim, H. (2003). Naphthalene and Hydronaphthalenes. In Ullmann's Encyclopedia of Industrial Chemistry. Weilheim: Wiley-VCH.]).

[Scheme 1]

Experimental

Crystal data

  • C16H20

  • Mr = 212.32

  • Orthorhombic, P b c a

  • a = 16.1044 (12) Å

  • b = 8.2099 (5) Å

  • c = 19.0303 (13) Å

  • V = 2516.1 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.06 mm−1

  • T = 150 K

  • 0.22 × 0.20 × 0.04 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.986, Tmax = 0.998

  • 12847 measured reflections

  • 2751 independent reflections

  • 2240 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.108

  • S = 1.04

  • 2751 reflections

  • 145 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C4/C9/C10 and C5–C10 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8—H8⋯Cg2i 0.95 2.88 3.7399 (15) 151
C11—H11⋯Cg1i 1.00 2.98 3.8289 (13) 144
C31—H31⋯Cg2ii 1.00 2.68 3.6048 (14) 155
Symmetry codes: (i) [x, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811047854/hb6496sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047854/hb6496Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047854/hb6496Isup3.cml

checkCIF report


Comment top

Alkylated naphthalenes have a wide spectrum of applications, ranging from solvents, insulating material, heat transfer fluids, dye works auxiliary and specialty lubricants, (Collin et al., 2003). Due to a variety of novel applications, diisopropylnaphthalene isomers have recently become of interest; they are used in the food packaging industry and as a plant growth regulator; furthermore, they have been introduced as PCB replacement fluids, (Addison,1983). The application of diisopropylnaphthalene isomer mixtures as solvents for carbonless copy paper, in its formulation known as KMC - Kureha Micro Capsule Oil - is of special importance. Some aromatic surfactants are partially based on propylated naphthalenes whose isomeric mixtures are used as water repelling agents for a variety of applications, such as corrosion protections, marine paints, resins,inks, coatings, plasticizers, or electrical, electronic and mechanical applications.

The main components of diisopropylnaphthalene isomer mixtures are 2,6-diisopropylnaphthalene and 2,7-diisopropylnaphthalene, contributing each with ca 40% to the mixture, while a few percent are made of the 1,3-, 1,6- and 1,7-diisopropylnaphthalenes, (Brzozowski et al., 2001). Diisopropylnaphthalenes with isopropyl groups positioned in adjacent ring positions are usually not detected in the mixtures. Separating all isomers or synthesizing them in pure form remains a challenging task.

The 1,3-isomer (I) is shown in Figure 1. The isopropyl methyl groups are oriented cis with respect to atom C2. The naphthalene-isopropyl torsion angles show that the orientations of the isopropyl groups around the C1—C11 and C3—C31 bonds with respect to the naphthalene ring is different in each case, e.g. C2—C1—C11—C111/C112 - 23.24 (17)°/100.54 (14)° and C2—C3—C31—C311/C312 64.27 (16)°/-60.14 (15)°. The orientation of the isopropyl group attached to C1 is unexpected in that unlike the group attached to C3 in which the hydrogen atom attached to C31 lies in the plane of the plane of the naphthalene ring that attached to C11 does not do so.

These orientations position the hydrogen atoms attached to C11 and C31 so that the molecules are linked by three C–H···π contacts to form a sheet lying in the ab plane, Table 1, Figure 2.

Related literature top

For background to diisopropylnaphthalenes, see: Addison (1983); Brzozowski et al. (2001); Collin et al. (2003).

Experimental top

Crystal of C16H20 were obtained from Rütgers Novares GmbH, Duisburg, Germany, with a stated purity greater than 98 percent and used as such.

Refinement top

Molecule (I) crystallized in the orthorhombic system; space group Pbca from the systematic absences. H atoms were treated as riding atoms with C—H(aromatic), 0.95 Å, C—H(aliphatic), 1.00 Å, with Uiso = 1.2Ueq(C), C—H(methyl), 0.98 Å,with Uiso = 1.5Ueq(C). The positions of the hydrogen atoms were confirmed in a final difference map.

Structure description top

Alkylated naphthalenes have a wide spectrum of applications, ranging from solvents, insulating material, heat transfer fluids, dye works auxiliary and specialty lubricants, (Collin et al., 2003). Due to a variety of novel applications, diisopropylnaphthalene isomers have recently become of interest; they are used in the food packaging industry and as a plant growth regulator; furthermore, they have been introduced as PCB replacement fluids, (Addison,1983). The application of diisopropylnaphthalene isomer mixtures as solvents for carbonless copy paper, in its formulation known as KMC - Kureha Micro Capsule Oil - is of special importance. Some aromatic surfactants are partially based on propylated naphthalenes whose isomeric mixtures are used as water repelling agents for a variety of applications, such as corrosion protections, marine paints, resins,inks, coatings, plasticizers, or electrical, electronic and mechanical applications.

The main components of diisopropylnaphthalene isomer mixtures are 2,6-diisopropylnaphthalene and 2,7-diisopropylnaphthalene, contributing each with ca 40% to the mixture, while a few percent are made of the 1,3-, 1,6- and 1,7-diisopropylnaphthalenes, (Brzozowski et al., 2001). Diisopropylnaphthalenes with isopropyl groups positioned in adjacent ring positions are usually not detected in the mixtures. Separating all isomers or synthesizing them in pure form remains a challenging task.

The 1,3-isomer (I) is shown in Figure 1. The isopropyl methyl groups are oriented cis with respect to atom C2. The naphthalene-isopropyl torsion angles show that the orientations of the isopropyl groups around the C1—C11 and C3—C31 bonds with respect to the naphthalene ring is different in each case, e.g. C2—C1—C11—C111/C112 - 23.24 (17)°/100.54 (14)° and C2—C3—C31—C311/C312 64.27 (16)°/-60.14 (15)°. The orientation of the isopropyl group attached to C1 is unexpected in that unlike the group attached to C3 in which the hydrogen atom attached to C31 lies in the plane of the plane of the naphthalene ring that attached to C11 does not do so.

These orientations position the hydrogen atoms attached to C11 and C31 so that the molecules are linked by three C–H···π contacts to form a sheet lying in the ab plane, Table 1, Figure 2.

For background to diisopropylnaphthalenes, see: Addison (1983); Brzozowski et al. (2001); Collin et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick 2008).

Figures top
[Figure 1] Fig. 1. A view of (I) with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Stereoview of the sheet formed by C—H···π interactions. Hydrogen atoms not involved in the motifs are not included.
1,3-Bis(propan-2-yl)naphthalene top
Crystal data top
C16H20Dx = 1.121 Mg m−3
Mr = 212.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 421 reflections
a = 16.1044 (12) Åθ = 3.9–23.6°
b = 8.2099 (5) ŵ = 0.06 mm−1
c = 19.0303 (13) ÅT = 150 K
V = 2516.1 (3) Å3Block, colourless
Z = 80.22 × 0.20 × 0.04 mm
F(000) = 928
Data collection top
Bruker SMART APEX CCD
diffractometer		2751 independent reflections
Radiation source: fine-focus sealed tube2240 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 27.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −12→20
Tmin = 0.986, Tmax = 0.998k = −10→8
12847 measured reflectionsl = −24→18
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: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0398P)2 + 0.9272P]
where P = (Fo2 + 2Fc2)/3
2751 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C16H20V = 2516.1 (3) Å3
Mr = 212.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 16.1044 (12) ŵ = 0.06 mm−1
b = 8.2099 (5) ÅT = 150 K
c = 19.0303 (13) Å0.22 × 0.20 × 0.04 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		2751 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2240 reflections with I > 2σ(I)
Tmin = 0.986, Tmax = 0.998Rint = 0.036
12847 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.04Δρmax = 0.19 e Å−3
2751 reflectionsΔρmin = −0.21 e Å−3
145 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
C10.35224 (7)0.39257 (16)0.18964 (7)0.0211 (3)
C110.30803 (7)0.23796 (16)0.16559 (7)0.0230 (3)
H110.25190.23660.18810.028*
C1110.29530 (9)0.22710 (18)0.08610 (7)0.0321 (3)
H11A0.26660.12520.07460.048*
H11B0.34940.22950.06250.048*
H11C0.26170.31960.07020.048*
C1120.35537 (8)0.08727 (17)0.19147 (8)0.0288 (3)
H11D0.3266−0.01140.17580.043*
H11E0.35800.08850.24290.043*
H11F0.41180.08840.17220.043*
C20.40246 (7)0.47957 (16)0.14496 (7)0.0223 (3)
H20.40660.44500.09740.027*
C30.44854 (7)0.61884 (15)0.16637 (7)0.0221 (3)
C310.50394 (8)0.70740 (16)0.11426 (7)0.0250 (3)
H310.53220.79790.14000.030*
C3110.45361 (9)0.78327 (18)0.05444 (8)0.0332 (3)
H31A0.49120.83940.02200.050*
H31B0.41380.86160.07380.050*
H31C0.42360.69750.02920.050*
C3120.57143 (8)0.59413 (18)0.08548 (8)0.0314 (3)
H31D0.60610.65390.05190.047*
H31E0.54540.50130.06180.047*
H31F0.60600.55480.12430.047*
C40.44313 (7)0.66789 (16)0.23492 (7)0.0225 (3)
H40.47380.76040.25000.027*
C50.38868 (8)0.63261 (16)0.35543 (7)0.0257 (3)
H50.42110.72240.37080.031*
C60.33889 (8)0.55295 (18)0.40250 (7)0.0283 (3)
H60.33720.58710.45020.034*
C70.29021 (8)0.42038 (17)0.38021 (7)0.0274 (3)
H70.25460.36710.41270.033*
C80.29370 (8)0.36748 (17)0.31199 (7)0.0245 (3)
H80.26090.27690.29810.029*
C90.34551 (7)0.44543 (16)0.26157 (7)0.0211 (3)
C100.39261 (7)0.58325 (16)0.28397 (7)0.0216 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0173 (6)0.0207 (6)0.0253 (7)0.0017 (5)−0.0029 (5)−0.0020 (5)
C110.0196 (6)0.0224 (7)0.0270 (7)−0.0032 (5)0.0008 (5)−0.0018 (6)
C1110.0374 (8)0.0291 (8)0.0297 (8)−0.0099 (6)−0.0043 (6)−0.0038 (6)
C1120.0272 (7)0.0230 (7)0.0360 (8)−0.0018 (6)−0.0002 (6)−0.0029 (6)
C20.0211 (6)0.0224 (7)0.0232 (6)0.0006 (5)−0.0012 (5)−0.0023 (6)
C30.0198 (6)0.0203 (7)0.0261 (7)0.0007 (5)−0.0028 (5)0.0000 (5)
C310.0275 (6)0.0212 (7)0.0261 (7)−0.0054 (5)−0.0002 (5)−0.0001 (6)
C3110.0401 (8)0.0279 (8)0.0317 (8)0.0006 (6)−0.0002 (6)0.0036 (6)
C3120.0277 (7)0.0324 (8)0.0342 (8)−0.0036 (6)0.0050 (6)−0.0010 (7)
C40.0204 (6)0.0191 (6)0.0280 (7)−0.0004 (5)−0.0041 (5)−0.0030 (5)
C50.0250 (6)0.0243 (7)0.0280 (7)0.0024 (5)−0.0045 (5)−0.0052 (6)
C60.0276 (7)0.0324 (8)0.0248 (7)0.0061 (6)−0.0003 (5)−0.0050 (6)
C70.0230 (6)0.0314 (8)0.0279 (7)0.0023 (6)0.0032 (5)0.0015 (6)
C80.0193 (6)0.0257 (7)0.0285 (7)−0.0005 (5)−0.0005 (5)−0.0017 (6)
C90.0164 (6)0.0212 (6)0.0257 (7)0.0035 (5)−0.0020 (5)−0.0012 (5)
C100.0182 (6)0.0211 (7)0.0253 (7)0.0042 (5)−0.0035 (5)−0.0024 (5)
Geometric parameters (Å, º) top
C1—C21.3738 (18)C311—H31A0.9800
C1—C91.4400 (18)C311—H31B0.9800
C1—C111.5256 (18)C311—H31C0.9800
C11—C1111.5291 (19)C312—H31D0.9800
C11—C1121.5344 (19)C312—H31E0.9800
C11—H111.0000C312—H31F0.9800
C111—H11A0.9800C4—C101.4199 (18)
C111—H11B0.9800C4—H40.9500
C111—H11C0.9800C5—C61.369 (2)
C112—H11D0.9800C5—C101.4203 (18)
C112—H11E0.9800C5—H50.9500
C112—H11F0.9800C6—C71.407 (2)
C2—C31.4228 (17)C6—H60.9500
C2—H20.9500C7—C81.3701 (19)
C3—C41.3680 (18)C7—H70.9500
C3—C311.5193 (18)C8—C91.4236 (18)
C31—C3111.5299 (19)C8—H80.9500
C31—C3121.5318 (19)C9—C101.4273 (18)
C31—H311.0000
C2—C1—C9118.42 (12)C31—C311—H31A109.5
C2—C1—C11121.44 (12)C31—C311—H31B109.5
C9—C1—C11120.05 (11)H31A—C311—H31B109.5
C1—C11—C111114.07 (11)C31—C311—H31C109.5
C1—C11—C112110.04 (10)H31A—C311—H31C109.5
C111—C11—C112109.70 (11)H31B—C311—H31C109.5
C1—C11—H11107.6C31—C312—H31D109.5
C111—C11—H11107.6C31—C312—H31E109.5
C112—C11—H11107.6H31D—C312—H31E109.5
C11—C111—H11A109.5C31—C312—H31F109.5
C11—C111—H11B109.5H31D—C312—H31F109.5
H11A—C111—H11B109.5H31E—C312—H31F109.5
C11—C111—H11C109.5C3—C4—C10121.29 (12)
H11A—C111—H11C109.5C3—C4—H4119.4
H11B—C111—H11C109.5C10—C4—H4119.4
C11—C112—H11D109.5C6—C5—C10121.09 (13)
C11—C112—H11E109.5C6—C5—H5119.5
H11D—C112—H11E109.5C10—C5—H5119.5
C11—C112—H11F109.5C5—C6—C7119.93 (13)
H11D—C112—H11F109.5C5—C6—H6120.0
H11E—C112—H11F109.5C7—C6—H6120.0
C1—C2—C3123.20 (12)C8—C7—C6120.54 (13)
C1—C2—H2118.4C8—C7—H7119.7
C3—C2—H2118.4C6—C7—H7119.7
C4—C3—C2118.45 (12)C7—C8—C9121.34 (13)
C4—C3—C31121.27 (12)C7—C8—H8119.3
C2—C3—C31120.26 (12)C9—C8—H8119.3
C3—C31—C311111.68 (11)C8—C9—C10117.81 (12)
C3—C31—C312111.07 (11)C8—C9—C1123.32 (12)
C311—C31—C312110.93 (12)C10—C9—C1118.87 (11)
C3—C31—H31107.7C4—C10—C5121.02 (12)
C311—C31—H31107.7C4—C10—C9119.74 (12)
C312—C31—H31107.7C5—C10—C9119.24 (12)
C2—C1—C11—C111−23.24 (17)C6—C7—C8—C9−0.8 (2)
C9—C1—C11—C111160.20 (12)C7—C8—C9—C10−1.32 (18)
C2—C1—C11—C112100.54 (14)C7—C8—C9—C1178.96 (12)
C9—C1—C11—C112−76.03 (14)C2—C1—C9—C8178.25 (12)
C9—C1—C2—C30.37 (18)C11—C1—C9—C8−5.08 (18)
C11—C1—C2—C3−176.25 (11)C2—C1—C9—C10−1.47 (17)
C1—C2—C3—C40.52 (19)C11—C1—C9—C10175.20 (11)
C1—C2—C3—C31179.01 (12)C3—C4—C10—C5178.59 (12)
C4—C3—C31—C311−117.29 (14)C3—C4—C10—C9−0.82 (18)
C2—C3—C31—C31164.27 (16)C6—C5—C10—C4178.83 (12)
C4—C3—C31—C312118.31 (14)C6—C5—C10—C9−1.76 (19)
C2—C3—C31—C312−60.14 (15)C8—C9—C10—C4−178.04 (11)
C2—C3—C4—C10−0.29 (18)C1—C9—C10—C41.70 (17)
C31—C3—C4—C10−178.76 (11)C8—C9—C10—C52.54 (17)
C10—C5—C6—C7−0.3 (2)C1—C9—C10—C5−177.73 (11)
C5—C6—C7—C81.6 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C4/C9/C10 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg2i0.952.883.7399 (15)151
C11—H11···Cg1i1.002.983.8289 (13)144
C31—H31···Cg2ii1.002.683.6048 (14)155
Symmetry codes: (i) x, −y−3/2, z−1/2; (ii) x+3/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formulaC16H20
Mr212.32
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)150
a, b, c (Å)16.1044 (12), 8.2099 (5), 19.0303 (13)
V (Å3)2516.1 (3)
Z8
Radiation typeMo Kα
µ (mm−1)0.06
Crystal size (mm)0.22 × 0.20 × 0.04
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.986, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections		12847, 2751, 2240
Rint0.036
(sin θ/λ)max (Å−1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.108, 1.04
No. of reflections2751
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick 2008).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C4/C9/C10 and C5–C10 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg2i0.952.883.7399 (15)151
C11—H11···Cg1i1.002.983.8289 (13)144
C31—H31···Cg2ii1.002.683.6048 (14)155
Symmetry codes: (i) x, −y−3/2, z−1/2; (ii) x+3/2, −y+1/2, −z.
 

Acknowledgements

The authors are grateful to Dr Bernd Godry and Rütgers Novares GmbH for the donation of a sample of the title compound. BS acknowledges the Fundação para a Ciência e a Tecnologia (FCT) and the European Social Fund (ESF) under the 3rd Community Support Framework (CSF) for the award of a post-doctoral grant (grant No. SFRH/BPD/38637/2007) and the award of research project PTDC/AAC-AMB/121161/2010.

References

First citationAddison, R. F. (1983). Environ. Sci. Technol. 17, 486A–494A.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBrzozowski, R., Dobrowolski, J. C., Jamróz, M. H. & Skupiński, W. (2001). J. Mol. Catal. A, 170, 95–99.  CrossRef CAS Google Scholar
 First citationCollin, G., Höke, H. & Greim, H. (2003). Naphthalene and Hydronaphthalenes. In Ullmann's Encyclopedia of Industrial Chemistry. Weilheim: Wiley-VCH.  Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  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 67| Part 12| December 2011| Page o3334
https://doi.org/10.1107/S1600536811047854
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