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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
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


Comment top

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 program to systematize in situ crystal growth from liquids, we have examined a range of commercially available chemicals. The low-molecular weight organic ketones are liquid at room temperature. The molecules of cyclohexanone, (I), exist as discrete entities, with no strong intermolecular contacts.

Experimental top

A 3 mm column of the title material, which is a liquid at room temperature, was sealed in a 0.2 mm Lindemann tube. The Lindemann tube was not accurately parallel to the ϕ axis. A single-crystal of the compound was grown by keeping the compound under a crystream (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 more-or-less-single-crystal specimen had been obtained, the main data collection was taken 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) also contain contributions due to changes in the illuminated volume of the cylindrical sample, which affects the value of Tmin/Tmax.

Refinement top

All H atoms were located in a difference map, and were repositioned geometrically with anisotropic displacement parameters related to the adjacent atoms. 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. As the absolute structure could not be determined reliably from the diffraction data, Freidel pairs were merged.

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.

Figures top
[Figure 1] Fig. 1. The title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are of arbitrary radii.
[Figure 2] Fig. 2. The crystal structure as viewed down the a axis.
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
Crystal data top
C6H10OV = 574.63 (4) Å3
Mr = 98.14Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.3736 (2) ŵ = 0.08 mm1
b = 7.0394 (3) ÅT = 150 K
c = 15.1910 (7) Å0.70 × 0.30 × 0.30 mm
Data collection top
Nonius KappaCCD
diffractometer
775 independent reflections
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
693 reflections with I > 2.00u(I)
Tmin = 0.74, Tmax = 0.98Rint = 0.085
1298 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å3
774 reflectionsΔρmin = 0.17 e Å3
64 parameters
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

Experimental details

Crystal data
Chemical formulaC6H10O
Mr98.14
Crystal system, space groupOrthorhombic, P212121
Temperature (K)150
a, b, c (Å)5.3736 (2), 7.0394 (3), 15.1910 (7)
V3)574.63 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.70 × 0.30 × 0.30
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.74, 0.98
No. of measured, independent and
observed [I > 2.00u(I)] reflections
1298, 775, 693
Rint0.085
(sin θ/λ)max1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.119, 1.02
No. of reflections774
No. of parameters64
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.17

Computer programs: COLLECT (Nonius, 1997), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996), CRYSTALS.

Selected geometric parameters (Å, º) top
C1—C21.501 (2)C3—C41.520 (3)
C1—C61.513 (2)C4—C51.523 (3)
C1—O71.213 (2)C5—C61.533 (2)
C2—C31.532 (3)
C2—C1—C6115.45 (14)C2—C3—C4111.63 (15)
C2—C1—O7122.61 (15)C3—C4—C5110.85 (16)
C6—C1—O7121.93 (15)C4—C5—C6111.04 (15)
C1—C2—C3112.29 (15)C5—C6—C1111.65 (13)
 

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.

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds