organic papers
o450
Klaus Merz C16H26 DOI: 10.1107/S1600536802004725 Acta Cryst.(2002). E58, o450±o451Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
1-Phenyldecane
Klaus Merz
Anorganische Chemie 1, Ruhr-UniversitaÈt Bochum, UniversitaÈtsstraûe 150, D-41801 Bochum, Germany
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study
T= 213 K
Mean(C±C) = 0.003 AÊ
Rfactor = 0.043
wRfactor = 0.124
Data-to-parameter ratio = 13.4
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
In the crystal structure of the title compound, C16H26, the
crystal packing is formed by a herring-bone arrangement of the phenyl rings.
Comment
Long-chain linear alkylbenzenes have been identi®ed in wastes (Valls et al., 1989), sediments (Ishiwatariet al., 1983) and suspended particles (Takada & Ishiwatari, 1987); these compounds are produced industrially as precursors for the anionic surfactants linear alkylbenzene sulfonates. The long-chain linear alkylbenzenes have both an aliphatic and aromatic nature because of their unique structure. This results in their having physical properties in the same range as other hydrocarbon atoms of interest, such as saturated hydrocarbon atoms, polynuclear aromatic hydrocarbon atoms and poly-chlorinated biphenyls (Sherblom & Eganhouse, 1991). We report here the structure and the crystal packing of 1-phenyldecane, (I), which has a melting point about 259 K and crystallizes in space groupP212121.
The molecular structure is shown in Fig. 1. As 1-phenyl-decane is a liquid, a special crystal growth technique was used. The title compound was ®rst puri®ed by distillation in high vacuum, and then transferred into an attached capillary. The sealed capillary was transferred to the diffractometer with a detachable cooling device. Single crystals suitable for X-ray diffraction were grown in situ using a computer-controlled
device that applied a focused CO2 laser beam along the
capillary (Boese et al., 1999). The molecular structure of (I) has a planar arrangement of the alkane carbon skeleton. The mean C(H3)ÐC(H2) and C(H2)ÐC(H2) distances, and the
mean C(H3)ÐC(H2)ÐC and C(H2)ÐC(H2)ÐC angles, are in
good agreement with those determined for n-alkanes
[1.521 (1) AÊ and 112.8 (1)±113.5 (1), respectively; Boese et al., 1999]. In the molecule, the phenyl ring and the alkane carbon skeleton are oriented at 84.73 (8)with respect to each
other. A search of the October 2001 release of the Cambridge
Structural Database (Allen et al., 1983) for structures
containing the C6H5(CH2)nCH3fragment withn> 1 revealed
no long-chain linear alkylbenzenes. In contrast to n-alkanes
and most end-substitutedn-alkanes (Kitaigorodskii, 1973), the long-chain linear alkylbenzenes do not show remarkable variation in their melting points. The crystal packing of 1-phenyldecane is shown in Fig. 2. This exhibits a herring-bone arrangement and the overall packing is similar to that of benzene, in the manner of 2-aminophenol, anothero -disub-stituted benzene (Allenet al., 1997). The CH2groups ®t into
the hollows of the neighbouring chains.
Experimental
Crystal data
C16H26
Mr= 218.37
Orthorhombic,P212121
a= 5.1428 (16) AÊ
b= 8.908 (3) AÊ
c= 31.687 (11) AÊ
V= 1451.7 (8) AÊ3
Z= 4
Dx= 0.999 Mg mÿ3
MoKradiation Cell parameters from 95
re¯ections
= 2.8±18.7
= 0.06 mmÿ1
T= 213 (2) K Cylinder, colourless
0.4 (length)0.2 mm (diameter)
Data collection
Bruker AXS CCD 1000 diffractometer
!scans
Absorption correction: multi-scan (Blessing, 1995)
Tmin= 0.970,Tmax= 0.991
6337 measured re¯ections
1941 independent re¯ections 1287 re¯ections withI> 2(I)
Rint= 0.037 max= 25.0
h=ÿ2!7
k=ÿ10!11
l=ÿ33!37
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.043
wR(F2) = 0.124
S= 1.02 1941 re¯ections 145 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0515P)2
+ 0.1408P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.002
max= 0.11 e AÊÿ3
min=ÿ0.15 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
C12ÐC13 1.511 (3) C12ÐC11 1.521 (3) C10ÐC11 1.515 (3) C10ÐC9 1.523 (3) C14ÐC15 1.505 (3) C14ÐC13 1.518 (3) C8ÐC9 1.512 (3) C8ÐC7 1.529 (3)
C15ÐC16 1.519 (3) C1ÐC6 1.376 (3) C1ÐC2 1.389 (3) C1ÐC7 1.501 (3) C3ÐC4 1.362 (3) C3ÐC2 1.375 (3) C5ÐC4 1.364 (4) C5ÐC6 1.372 (3) C13ÐC12ÐC11 114.05 (17)
C11ÐC10ÐC9 113.74 (17) C15ÐC14ÐC13 113.95 (17) C10ÐC11ÐC12 113.93 (17) C12ÐC13ÐC14 113.87 (17) C9ÐC8ÐC7 113.28 (18) C8ÐC9ÐC10 113.60 (18) C14ÐC15ÐC16 113.7 (2) C6ÐC1ÐC2 117.4 (2)
C6ÐC1ÐC7 120.9 (2) C2ÐC1ÐC7 121.6 (2) C1ÐC7ÐC8 112.70 (17) C4ÐC3ÐC2 119.9 (2) C3ÐC2ÐC1 121.2 (2) C4ÐC5ÐC6 120.5 (2) C5ÐC6ÐC1 121.1 (2) C3ÐC4ÐC5 119.8 (2)
All H atoms, visible in difference maps, were positioned geome-trically and included as riding atoms in the re®nement. Friedel pairs were merged, because of the absence of signi®cant anomalous scat-tering effects.
Data collection:SMART(Siemens, 1996); cell re®nement:SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Siemens, 1996); program(s) used to re®ne structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTL.
References
Allen, F. H., Hoy, V. J., Howard, J. A. K., Thalladi, V. R., Desiraju, G. R., Wilson, C. C. & McIntyre, G. J. J. (1997).J. Am. Chem. Soc.119, 3477±3480. Allen, F. H., Kennard, O. & Taylor, R. (1983).Acc. Chem. Res.16, 146±153. Blessing, R. H. (1995).Acta Cryst.A51, 33±38.
Boese, R., Weiss, Weiss, H.-C. & Blaeser D. (1999).Angew. Chem. Int. Ed.38, 988±992.
Ishiwatari, R., Takada, H., Yun, S. J. & Matsumoto, E. (1983). Nature (London),301, 599±600.
Kitaigorodskii, A. I. (1973). Molecular Crystals and Molecules. New York: Academic Press.
Sherblom, P. M. & Eganhouse, R. P. (1991).Organic Substances and Sediments in Water, Vol. 3,Biological, edited by R. A. Baker, pp. 139±158. Chelsea, Michigan: Lewis Publishers.
Siemens (1996). SHELXTL (Version 5.10/DOS/WIN95/NT),SMART and
SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Takada, H. & Ishiwatari, R. (1987).Environ. Sci. Technol.21, 875±883. Valls, M., Bayona, J. M. & Albaiges, J. (1989).Nature (London),337, 722±724.
Figure 2
The crystal packing of (I), showing the herring-bone packing of the molecules.
Figure 1
supporting information
sup-1 Acta Cryst. (2002). E58, o450–o451
supporting information
Acta Cryst. (2002). E58, o450–o451 [https://doi.org/10.1107/S1600536802004725]
1-Phenyldecane
Klaus Merz
(I)
Crystal data C16H26
Mr = 218.37
Orthorhombic, P212121
a = 5.1428 (16) Å b = 8.908 (3) Å c = 31.687 (11) Å V = 1451.7 (8) Å3
Z = 4 F(000) = 488
Dx = 0.999 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 95 reflections θ = 2.8–18.7°
µ = 0.06 mm−1
T = 213 K
Cylinder, colourless 0.4 × 0.2 × 0.2 mm
Data collection
Bruker AXS CCD 1000 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: empirical (using intensity measurements)
(Blessing, 1995) Tmin = 0.970, Tmax = 0.991
6337 measured reflections 1941 independent reflections 1287 reflections with I > 2σ(I) Rint = 0.037
θmax = 25.0°, θmin = 2.6°
h = −2→7 k = −10→11 l = −33→37
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.043
wR(F2) = 0.124
S = 1.02 1941 reflections 145 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0515P)2 + 0.1408P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002
Δρmax = 0.11 e Å−3
Special details
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)
x y z Uiso*/Ueq
supporting information
sup-3 Acta Cryst. (2002). E58, o450–o451
H3A 0.3990 −0.2111 0.7374 0.079* C2 0.6538 (5) −0.1234 (3) 0.77901 (8) 0.0565 (6) H2A 0.5848 −0.1726 0.8027 0.068* C5 0.8497 (5) 0.0174 (3) 0.70955 (8) 0.0655 (7) H5A 0.9171 0.0662 0.6856 0.079* C6 0.9616 (5) 0.0406 (3) 0.74830 (8) 0.0586 (6) H6A 1.1059 0.1049 0.7506 0.070* C4 0.6412 (6) −0.0762 (3) 0.70546 (9) 0.0666 (7) H4A 0.5657 −0.0919 0.6788 0.080*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C12 0.0471 (11) 0.0471 (12) 0.0427 (12) 0.0013 (10) −0.0018 (10) 0.0029 (10) C10 0.0488 (11) 0.0475 (12) 0.0417 (12) 0.0025 (10) −0.0021 (10) 0.0032 (10) C14 0.0481 (11) 0.0472 (12) 0.0394 (12) 0.0012 (10) 0.0004 (10) 0.0047 (10) C11 0.0475 (10) 0.0479 (11) 0.0425 (12) −0.0005 (10) −0.0021 (10) 0.0021 (10) C13 0.0458 (11) 0.0463 (12) 0.0434 (13) 0.0006 (10) −0.0035 (10) 0.0026 (10) C8 0.0452 (10) 0.0480 (12) 0.0406 (12) 0.0029 (10) −0.0003 (9) 0.0025 (10) C9 0.0462 (10) 0.0510 (13) 0.0445 (13) 0.0051 (10) −0.0029 (10) 0.0011 (10) C15 0.0627 (13) 0.0520 (13) 0.0429 (13) −0.0006 (12) −0.0016 (12) 0.0019 (11) C1 0.0450 (10) 0.0461 (11) 0.0449 (13) 0.0108 (10) −0.0006 (10) −0.0025 (10) C16 0.0881 (19) 0.0601 (16) 0.0479 (15) −0.0008 (15) 0.0045 (14) −0.0050 (11) C7 0.0556 (12) 0.0647 (15) 0.0465 (14) 0.0153 (12) −0.0040 (11) −0.0036 (12) C3 0.0572 (14) 0.0635 (16) 0.0777 (19) −0.0034 (13) −0.0145 (14) −0.0076 (15) C2 0.0532 (12) 0.0575 (14) 0.0590 (16) 0.0033 (12) 0.0051 (12) 0.0030 (12) C5 0.0704 (15) 0.0778 (17) 0.0484 (15) 0.0054 (15) 0.0001 (13) 0.0053 (13) C6 0.0532 (12) 0.0664 (15) 0.0563 (15) −0.0059 (12) −0.0012 (11) −0.0013 (12) C4 0.0704 (16) 0.0701 (16) 0.0594 (17) 0.0132 (15) −0.0152 (14) −0.0114 (14)
Geometric parameters (Å, º)
C8—C9 1.512 (3) C5—C4 1.364 (4) C8—C7 1.529 (3) C5—C6 1.372 (3) C8—H8A 0.9800 C5—H5A 0.9400 C8—H8B 0.9800 C6—H6A 0.9400 C9—H9A 0.9800 C4—H4A 0.9400
