Acta Cryst.(2001). E57, o1189±o1190 DOI: 10.1107/S1600536801019237 Nobuhiro Yasudaet al. C8H8
o1189
organic papers
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
Styrene at 83 K
Nobuhiro Yasuda, Hidehiro Uekusa* and Yuji Ohashi
Department of Chemistry and Materials Science, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study
T= 83 K
Mean(C±C) = 0.002 AÊ
Rfactor = 0.039
wRfactor = 0.099
Data-to-parameter ratio = 13.5
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2001 International Union of Crystallography Printed in Great Britain ± all rights reserved
The single crystal of the title compound, C8H8, was obtained
byin situcrystallization. The torsion angle between the phenyl ring and the vinyl group is 7.82 (17). The double-bond length
in the vinyl group is 1.3245 (16) AÊ, which is slightly shorter than a normal C C double bond.
Comment
Styrene, (I), is one of the most widely used compounds in synthetic polymer science and theoretical calculations. Thus, determination of the crystal structure of styrene is very important to establish its chemical properties and to compare it with the structure derived by theoretical calculation. However, the crystal structure has not yet been reported because styrene is liquid at room temperature (m.p. 242.5 K). In this study, a single crystal of styrene was obtained by thein situ crystallization method, and the crystal structure was determined by the single-crystal X-ray diffraction method at 83 K.
The molecular structure is nearly planar, the torsion angle between the phenyl ring and the vinyl group being 7.82 (17).
The C7 C8 vinyl double bond is 1.3245 (16) AÊ. These values are almost the same as those in 4-vinylbenzoic acid, 9.06 (16)
and 1.3248 (14) AÊ at 108 K, respectively (Yasudaet al., 2000). However, these vinyl bond lengths are slightly shorter than the normal C C double-bond length of 1.34 AÊ.
Note added to proof: this work and the following study of Bond & Davies (2001) were carried out independently.
Experimental
The title compound, (I), was purchased from Aldrich Chemical Company Inc. A single crystal was obtained by thein situ crystal-lization method (Boese & Nussbaumer, 1994) in a 0.3 mm diameter glass capillary and was cooled to 83 K by the nitrogen gas ¯ow method for data collection.
Crystal data C8H8
Mr= 104.14
Orthorhombic,Pbcn a= 15.6757 (12) AÊ b= 10.4805 (8) AÊ c= 7.5277 (6) AÊ V= 1236.72 (17) AÊ3
Z= 8
Dx= 1.119 Mg mÿ3
MoKradiation
Cell parameters from 11 393 re¯ections
= 3.6±27.5
= 0.06 mmÿ1
T= 83 (2) K Cylindrical, colorless Radius: 0.3 mm
Data collection
RigakuR-AXIS RAPID Imaging Plate diffractometer
'scans
Absorption correction: none 11 393 measured re¯ections 1417 independent re¯ections
1255 re¯ections withI> 2(I) Rint= 0.059
max= 27.5
h=ÿ19!20 k=ÿ13!12 l=ÿ9!9
Re®nement Re®nement onF2
R[F2> 2(F2)] = 0.039
wR(F2) = 0.099
S= 1.04 1417 re¯ections 105 parameters
All H-atom parameters re®ned
w= 1/[2(F
o2) + (0.0404P)2
+ 0.3865P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.19 e AÊÿ3
min=ÿ0.18 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
C1ÐC6 1.3951 (14)
C1ÐC2 1.4017 (14)
C1ÐC7 1.4737 (14)
C2ÐC3 1.3878 (14)
C3ÐC4 1.3922 (16)
C4ÐC5 1.3882 (15)
C5ÐC6 1.3901 (14)
C7ÐC8 1.3245 (16)
C2ÐC1ÐC7ÐC8 7.82 (17)
All H atoms were located from difference Fourier maps. Their positional and isotropic displacement parameters were re®ned. The CÐH bond lengths are 0.968 (16)±1.008 (14) AÊ.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell re®ne-ment:PROCESS-AUTO; data reduction:TEXSAN(Rigaku, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP3 for Windows (Farrugia, 1998); software used to prepare material for publication:SHELXL97.
References
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999).J. Appl. Cryst.32, 115±119.
Boese, R. & Nussbaumer, M. (1994). Correlations, Transformations, and Interactions in Organic Crystal Chemistry, edited by D. W. Jones and A. Katrusiak, pp. 20±37. Oxford: Oxford University Press.
Bond, A. D. & Davies, J. E. (2001).Acta Cryst.E57, o1191±o1193.
Farrugia, L. J. (1998).ORTEP3 for Windows. University of Glasgow, Scotland. Rigaku (1998).PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Rigaku (1999).TEXSAN.Version 1.10. Rigaku Corporation, Tokyo, Japan. Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Yasuda, N., Uekusa, H. & Ohashi, Y. (2000).Acta Cryst.C56, 1364±1366. Figure 2
The crystal packing of (I), viewed along thecaxis. H atoms have been omitted.
Figure 1
supporting information
sup-1 Acta Cryst. (2001). E57, o1189–o1190
supporting information
Acta Cryst. (2001). E57, o1189–o1190 [https://doi.org/10.1107/S1600536801019237]
Styrene at 83
K
Nobuhiro Yasuda, Hidehiro Uekusa and Yuji Ohashi
styrene
Crystal data
C8H8 Mr = 104.14
Orthorhombic, Pbcn a = 15.6757 (12) Å
b = 10.4805 (8) Å
c = 7.5277 (6) Å
V = 1236.72 (17) Å3 Z = 8
F(000) = 448
Dx = 1.119 Mg m−3
Melting point: 242.5 K
Mo Kα radiation, λ = 0.71069 Å Cell parameters from 11393 reflections
θ = 3.6–27.5°
µ = 0.06 mm−1 T = 83 K
Cylindrical, colorless 0.3 × 0.3 × 0.3 mm
Data collection
Rigaku R-AXIS RAPID Imaging Plate diffractometer
Radiation source: Rigaku ratating anode Ultrax18
Graphite monochromator
Detector resolution: 10 pixels mm-1
Oscillation Photograph scans 11393 measured reflections
1417 independent reflections 1255 reflections with I > 2σ(I)
Rint = 0.059
θmax = 27.5°, θmin = 3.6° h = −19→20
k = −13→12
l = −9→9
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.039 wR(F2) = 0.099 S = 1.04 1417 reflections 105 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
All H-atom parameters refined
w = 1/[σ2(F
o2) + (0.0404P)2 + 0.3865P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.19 e Å−3
Δρmin = −0.18 e Å−3
Special details
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
C1 0.26525 (6) 0.14911 (9) 0.43547 (12) 0.0207 (2)
C2 0.29626 (7) 0.05101 (10) 0.54433 (13) 0.0223 (2)
H2 0.2578 (8) −0.0165 (13) 0.5869 (16) 0.027 (3)*
C3 0.38153 (7) 0.04777 (10) 0.59374 (13) 0.0240 (2)
H3 0.4012 (8) −0.0209 (13) 0.6708 (18) 0.032 (3)*
C4 0.43785 (7) 0.14117 (10) 0.53422 (13) 0.0246 (3)
H4 0.5000 (9) 0.1371 (12) 0.5685 (17) 0.032 (3)*
C5 0.40803 (7) 0.23798 (10) 0.42473 (13) 0.0243 (2)
H5 0.4473 (8) 0.3053 (13) 0.3816 (17) 0.030 (3)*
C6 0.32249 (7) 0.24176 (10) 0.37636 (13) 0.0228 (2)
H6 0.3008 (8) 0.3108 (12) 0.2991 (17) 0.030 (3)*
C7 0.17514 (6) 0.15764 (11) 0.38098 (13) 0.0249 (3)
H7 0.1623 (8) 0.2238 (13) 0.2928 (19) 0.037 (4)*
C8 0.11121 (7) 0.08637 (11) 0.43922 (15) 0.0302 (3)
H8A 0.1176 (9) 0.0218 (15) 0.530 (2) 0.042 (4)*
H8B 0.0527 (10) 0.1014 (13) 0.3947 (19) 0.042 (4)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0229 (5) 0.0243 (5) 0.0150 (4) 0.0031 (4) 0.0006 (3) −0.0023 (3)
C2 0.0258 (5) 0.0233 (5) 0.0177 (4) 0.0027 (4) 0.0018 (4) 0.0000 (4)
C3 0.0274 (5) 0.0261 (5) 0.0185 (5) 0.0078 (4) 0.0002 (4) 0.0008 (4)
C4 0.0224 (5) 0.0310 (6) 0.0205 (5) 0.0055 (4) 0.0000 (4) −0.0051 (4)
C5 0.0251 (5) 0.0271 (5) 0.0206 (5) −0.0016 (4) 0.0030 (4) −0.0031 (4)
C6 0.0265 (5) 0.0244 (5) 0.0175 (5) 0.0029 (4) 0.0007 (4) 0.0012 (4)
C7 0.0247 (5) 0.0288 (6) 0.0212 (5) 0.0047 (4) −0.0023 (4) 0.0000 (4)
C8 0.0248 (5) 0.0336 (6) 0.0322 (6) 0.0016 (4) −0.0018 (4) −0.0033 (5)
Geometric parameters (Å, º)
C1—C6 1.3951 (14) C4—H4 1.008 (14)
C1—C2 1.4017 (14) C5—C6 1.3901 (14)
C1—C7 1.4737 (14) C5—H5 0.991 (13)
C2—C3 1.3878 (14) C6—H6 0.989 (13)
C2—H2 0.984 (13) C7—C8 1.3245 (16)
C3—C4 1.3922 (16) C7—H7 0.980 (14)
C3—H3 0.974 (14) C8—H8A 0.968 (16)
supporting information
sup-3 Acta Cryst. (2001). E57, o1189–o1190
C6—C1—C2 118.29 (9) C4—C5—C6 120.07 (10)
C6—C1—C7 119.05 (9) C4—C5—H5 120.4 (7)
C2—C1—C7 122.66 (9) C6—C5—H5 119.5 (7)
C3—C2—C1 120.57 (10) C5—C6—C1 121.14 (10)
C3—C2—H2 119.0 (7) C5—C6—H6 120.5 (7)
C1—C2—H2 120.4 (7) C1—C6—H6 118.4 (7)
C2—C3—C4 120.48 (9) C8—C7—C1 126.79 (10)
C2—C3—H3 118.9 (7) C8—C7—H7 117.8 (8)
C4—C3—H3 120.7 (7) C1—C7—H7 115.4 (8)
C5—C4—C3 119.44 (10) C7—C8—H8A 123.3 (9)
C5—C4—H4 120.5 (8) C7—C8—H8B 119.9 (8)
C3—C4—H4 120.0 (7) H8A—C8—H8B 116.6 (12)
C6—C1—C2—C3 0.95 (14) C4—C5—C6—C1 −0.25 (15)
C7—C1—C2—C3 −179.29 (9) C2—C1—C6—C5 −0.46 (14)
C1—C2—C3—C4 −0.74 (15) C7—C1—C6—C5 179.77 (9)
C2—C3—C4—C5 0.02 (15) C6—C1—C7—C8 −172.42 (11)
