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

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ISSN: 2056-9890

Cyclo­hexa­none at 150 K

aChemical Crystallography Laboratory, Chemistry Research Laboratory, Mansfield Road, Oxford University, Oxford OX1 3TA, England
*Correspondence e-mail: howard.shallard-brown@lmh.ox.ac.uk

(Received 12 May 2005; accepted 19 May 2005; online 9 July 2005)

The structure of cyclo­hexa­none, C6H10O, at 150 K is that of discrete mol­ecules, with no strong intermolecular interactions.

Comment

Many of the esters and ketones used in the flavours and fragrances industry are liquid at room temperature, meaning that, in the past, crystalline derivatives have had to be prepared for X-ray analysis. As part of a programme to systematize in situ crystal growth from liquids, we have examined a range of commercially available chemicals. Low-mol­ecular weight organic ketones are liquid at room temperature. The mol­ecules of cyclo­hexa­none, (I)[link], exist in the crystal structure at 150 K as discrete entities, with no strong inter­molecular interactions.

[Scheme 1]
[Figure 1]
Figure 1
The title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are of arbitrary radii.
[Figure 2]
Figure 2
The crystal structure, viewed down the a axis.

Experimental

A 3 mm column of the title material, which is a liquid at room temperature, was sealed in a 0.3 mm Lindemann tube. The Lindemann tube was not precisely parallel to the φ axis. A single crystal of the compound was grown by keeping the compound under a cold nitrogen gas stream (Oxford Cryostream 600) at 180 K and slowly moving a small liquid zone, created by a micro-heating coil, up and down the sample. Once a suitable approximately single-crystal specimen had been obtained, the main data collection was carried out at 150 K. Because not all of the data were collected with the Lindemann tube perpendicular to the X-ray beam, the multi-scan corrections applied by DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) also contain contributions due to changes in the illuminated volume of the cylindrical sample, which affects the value of Tmin/Tmax.

Crystal data
  • C6H10O

  • Mr = 98.14

  • Orthorhombic, P 21 21 21

  • a = 5.3736 (2) Å

  • b = 7.0394 (3) Å

  • c = 15.1910 (7) Å

  • V = 574.63 (4) Å3

  • Z = 4

  • Dx = 1.134 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 784 reflections

  • θ = 5–27°

  • μ = 0.08 mm−1

  • T = 150 K

  • Cylinder, colourless

  • 0.70 × 0.30 × 0.30 mm

Data collection
  • Nonius KappaCCD diffractometer

  • ω scans

  • Absorption correction: multi-scan(DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.])Tmin = 0.74, Tmax = 0.98

  • 9235 measured reflections

  • 775 independent reflections

  • 693 reflections with I > 2σ(I)

  • Rint = 0.085

  • θmax = 27.4°

  • h = −6 → 6

  • k = −9 → 9

  • l = −19 → 19

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.119

  • S = 1.02

  • 774 reflections

  • 64 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(F) + 0.08 + 0.07P], where P = (max(Fo2, 0) + 2Fc2)/3

  • (Δ/σ)max = 0.009

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Selected geometric parameters (Å, °)[link]

C1—C2 1.501 (2)
C1—C6 1.513 (2)
C1—O7 1.213 (2)
C2—C3 1.532 (3)
C3—C4 1.520 (3)
C4—C5 1.523 (3)
C5—C6 1.533 (2)
C2—C1—C6 115.45 (14)
C2—C1—O7 122.61 (15)
C6—C1—O7 121.93 (15)
C1—C2—C3 112.29 (15)
C2—C3—C4 111.63 (15)
C3—C4—C5 110.85 (16)
C4—C5—C6 111.04 (15)
C5—C6—C1 111.65 (13)

All H atoms were located in a difference map and were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry [C—H = 0.97–1.01 Å, and Uiso(H) = 1.2Ueq(C)], after which they were refined with riding constraints. In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Data collection: COLLECT (Nonius, 1997[Nonius (1997). COLLECT. Nonius Bv, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: CRYSTALS.

Supporting information


Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO/SCALEPACK; data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

cyclohexanone top
Crystal data top
C6H10ODx = 1.134 Mg m3
Mr = 98.14Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 784 reflections
a = 5.3736 (2) Åθ = 5–27°
b = 7.0394 (3) ŵ = 0.08 mm1
c = 15.1910 (7) ÅT = 150 K
V = 574.63 (4) Å3Cylinder, colourless
Z = 40.70 × 0.30 × 0.30 mm
F(000) = 216
Data collection top
Nonius KappaCCD
diffractometer
693 reflections with I > 2.00u(I)
Graphite monochromatorRint = 0.085
ω scansθmax = 27.4°, θmin = 5.5°
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
h = 66
Tmin = 0.74, Tmax = 0.98k = 99
1298 measured reflectionsl = 1919
775 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(F) + 0.08 + 0.07P],
where P = (max(Fo2, 0) + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.009
774 reflectionsΔρmax = 0.21 e Å3
64 parametersΔρmin = 0.17 e Å3
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4923 (3)0.1736 (2)0.09182 (10)0.0307
C20.2508 (3)0.1748 (3)0.14147 (11)0.0371
C30.2225 (4)0.0010 (3)0.20128 (12)0.0402
C40.2700 (4)0.1828 (3)0.15156 (12)0.0415
C50.5273 (4)0.1814 (3)0.10946 (12)0.0374
C60.5570 (3)0.0119 (2)0.04697 (11)0.0335
O70.6256 (3)0.31225 (18)0.08656 (8)0.0464
H210.24630.29050.17680.0499*
H220.11330.17910.09870.0414*
H310.34430.01160.24900.0582*
H320.05100.00260.22720.0704*
H410.25470.28800.19300.0476*
H420.14590.20020.10350.0472*
H510.65350.17460.15580.0408*
H520.54850.29880.07510.0569*
H610.72810.00980.02430.0502*
H620.44600.02700.00280.0385*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0397 (9)0.0260 (8)0.0264 (7)0.0019 (8)0.0023 (7)0.0051 (7)
C20.0423 (10)0.0316 (9)0.0374 (9)0.0061 (9)0.0026 (8)0.0016 (8)
C30.0448 (10)0.0381 (10)0.0377 (9)0.0034 (9)0.0097 (8)0.0014 (7)
C40.0473 (11)0.0297 (10)0.0474 (10)0.0084 (9)0.0056 (9)0.0014 (8)
C50.0415 (9)0.0250 (9)0.0458 (9)0.0020 (8)0.0010 (8)0.0010 (8)
C60.0348 (9)0.0322 (9)0.0337 (8)0.0020 (8)0.0033 (7)0.0003 (7)
O70.0586 (9)0.0321 (7)0.0484 (8)0.0108 (7)0.0037 (7)0.0024 (6)
Geometric parameters (Å, º) top
C1—C21.501 (2)C4—C51.523 (3)
C1—C61.513 (2)C4—H410.976
C1—O71.213 (2)C4—H420.997
C2—C31.532 (3)C5—C61.533 (2)
C2—H210.976C5—H510.979
C2—H220.984C5—H520.984
C3—C41.520 (3)C6—H610.982
C3—H310.980C6—H620.969
C3—H321.002
C2—C1—C6115.45 (14)C5—C4—H41110.615
C2—C1—O7122.61 (15)C3—C4—H42110.906
C6—C1—O7121.93 (15)C5—C4—H42107.479
C1—C2—C3112.29 (15)H41—C4—H42108.838
C1—C2—H21107.617C4—C5—C6111.04 (15)
C3—C2—H21109.743C4—C5—H51109.079
C1—C2—H22108.516C6—C5—H51109.579
C3—C2—H22109.952C4—C5—H52108.806
H21—C2—H22108.626C6—C5—H52108.260
C2—C3—C4111.63 (15)H51—C5—H52110.060
C2—C3—H31108.170C5—C6—C1111.65 (13)
C4—C3—H31108.700C5—C6—H61109.048
C2—C3—H32110.150C1—C6—H61111.075
C4—C3—H32109.123C5—C6—H62109.512
H31—C3—H32109.015C1—C6—H62107.729
C3—C4—C5110.85 (16)H61—C6—H62107.731
C3—C4—H41108.144
 

References

First citationAltomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals
First citationBetteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals
First citationNonius (1997). COLLECT. Nonius Bv, Delft, The Netherlands.
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
First citationWatkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.

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