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The crystal structure of (1R)-(-)-fenchone, C10H16O, has been determined at 150 (2) K following in situ crystal growth from the liquid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016932/cf6114sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016932/cf6114Isup2.hkl
Contains datablock I

CCDC reference: 176007

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.156
  • Data-to-parameter ratio = 8.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.783 1.000 Tmin' and Tmax expected: 1.000 1.000 RR' = 0.783 Please check that your absorption correction is appropriate. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 821 Count of symmetry unique reflns 834 Completeness (_total/calc) 98.44% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Fenchone (I) occurs in nature and may be extracted from fennel oil and thuja oil. An account of its history and the determination of its structure using the techniques of classical organic chemistry is given by Simonsen & Owen (1947). This work forms part of a continuing study devoted to improving the techniques for determining the crystal structures of substances which are liquids at room temperature (see, for example, Davies & Bond, 2001).

Experimental top

(1R)-(-)-Fenchone (98%) was obtained from the Aldrich company and used without further purification. The crystal was grown in a 0.3 mm glass capillary tube at 260 K (a temperature only slightly less than the melting point of the solid in the capillary tube). With the axis of the capillary parallel to the ϕ axis and horizontal on the instrument, the crystal was obtained by moving a plug of solid material up and down the tube (the movement being controlled with the standard height adjustment of the goniometer head). The length of the cylindrical crystal was not estimated, but it exceeded the 0.35 mm diameter of the collimator. Data were collected at 150 K.

Refinement top

Hydrogen atoms were placed geometrically and refined using a riding model with an isotropic displacement parameter fixed at 1.2 times Ueq for the carbon to which they are attached. The absolute configuration could not be determined reliably and was assigned according to the known configuration of the sample. Friedel pairs were merged prior to merging in P21; the reported value of Rint corresponds to subsequent merging of equivalent reflections in this space group.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing displacement ellipsoids at the 50% probability level (XP; Sheldrick, 1993).
[Figure 2] Fig. 2. Projection of the structure of (I) on to (100) (CAMERON; Watkin et al., 1996).
(-)-1,3,3-trimethyl-2-norbornanone top
Crystal data top
C10H16ODx = 1.135 Mg m3
Mr = 152.23Melting point: 278 K
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
a = 6.0520 (7) ÅCell parameters from 2665 reflections
b = 10.2748 (7) Åθ = 1.0–25.0°
c = 7.1621 (9) ŵ = 0.07 mm1
β = 91.335 (4)°T = 150 K
V = 445.24 (8) Å3Cylinder, colourless
Z = 20.15 mm (radius)
F(000) = 168
Data collection top
Nonius KappaCCD
diffractometer
757 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
Thin–slice ω and ϕ scansθmax = 25.0°, θmin = 4.0°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 77
Tmin = 0.783, Tmax = 1.000k = 1210
2506 measured reflectionsl = 68
821 independent reflections
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.1005P)2 + 0.0865P]
where P = (Fo2 + 2Fc2)/3
821 reflections(Δ/σ)max = 0.001
103 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
C10H16OV = 445.24 (8) Å3
Mr = 152.23Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.0520 (7) ŵ = 0.07 mm1
b = 10.2748 (7) ÅT = 150 K
c = 7.1621 (9) Å0.15 mm (radius)
β = 91.335 (4)°
Data collection top
Nonius KappaCCD
diffractometer
821 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
757 reflections with I > 2σ(I)
Tmin = 0.783, Tmax = 1.000Rint = 0.078
2506 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.157H-atom parameters constrained
S = 1.10Δρmax = 0.19 e Å3
821 reflectionsΔρmin = 0.22 e Å3
103 parameters
Special details top

Experimental. Grown in situ in a 0.3 mm Lindemann tube at 260 K. The absolute structure was assigned from the known configuration of the material and Friedel pairs were merged for refinement.

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
O10.3206 (5)0.6557 (3)0.9979 (4)0.0382 (8)
C10.2451 (6)0.7491 (4)0.6890 (5)0.0288 (9)
C20.2344 (6)0.7388 (3)0.8999 (5)0.0269 (8)
C30.0983 (6)0.8536 (4)0.9685 (5)0.0282 (8)
C40.0405 (6)0.9233 (4)0.7811 (5)0.0270 (8)
H40.09120.98180.78550.032*
C50.2476 (6)0.9870 (4)0.7011 (5)0.0297 (9)
H5A0.32061.04510.79390.036*
H5B0.21071.03750.58680.036*
C60.3949 (6)0.8690 (4)0.6567 (5)0.0312 (8)
H6A0.52690.86660.74090.037*
H6B0.44360.87220.52570.037*
C70.0140 (6)0.8069 (4)0.6455 (5)0.0294 (8)
H7A0.10730.74760.68000.035*
H7B0.00480.83450.51360.035*
C80.3129 (8)0.6255 (4)0.5892 (6)0.0380 (10)
H8A0.31250.64100.45420.057*
H8B0.20840.55570.61710.057*
H8C0.46170.60000.63200.057*
C90.1120 (7)0.8032 (4)1.0608 (5)0.0331 (9)
H9A0.19840.75140.97030.050*
H9B0.20070.87711.10220.050*
H9C0.07100.74891.16860.050*
C100.2299 (7)0.9334 (4)1.1118 (5)0.0354 (9)
H10A0.36860.96231.05720.053*
H10B0.26260.87981.22220.053*
H10C0.14331.00951.14810.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0414 (17)0.0372 (16)0.0360 (15)0.0090 (13)0.0021 (11)0.0087 (13)
C10.0282 (19)0.033 (2)0.0250 (19)0.0018 (15)0.0037 (14)0.0006 (15)
C20.0249 (18)0.0267 (17)0.0292 (18)0.0019 (14)0.0024 (14)0.0023 (16)
C30.0284 (18)0.0318 (19)0.0246 (16)0.0006 (16)0.0051 (13)0.0005 (15)
C40.0278 (18)0.0279 (17)0.0254 (17)0.0028 (15)0.0022 (13)0.0031 (15)
C50.034 (2)0.0290 (18)0.0264 (19)0.0005 (15)0.0051 (15)0.0035 (14)
C60.0312 (19)0.0349 (19)0.0277 (17)0.0028 (17)0.0067 (14)0.0015 (17)
C70.0284 (19)0.0330 (18)0.0267 (18)0.0014 (15)0.0001 (14)0.0036 (15)
C80.043 (2)0.036 (2)0.036 (2)0.0057 (18)0.0070 (17)0.0060 (18)
C90.031 (2)0.0334 (19)0.035 (2)0.0015 (16)0.0112 (15)0.0000 (16)
C100.039 (2)0.038 (2)0.0298 (19)0.0048 (19)0.0029 (16)0.0033 (17)
Geometric parameters (Å, º) top
O1—C21.216 (4)C5—H5B0.990
C1—C21.517 (5)C6—H6A0.990
C1—C81.518 (5)C6—H6B0.990
C1—C71.545 (5)C7—H7A0.990
C1—C61.550 (5)C7—H7B0.990
C2—C31.527 (5)C8—H8A0.980
C3—C101.524 (5)C8—H8B0.980
C3—C91.538 (5)C8—H8C0.980
C3—C41.554 (5)C9—H9A0.980
C4—C51.537 (5)C9—H9B0.980
C4—C71.546 (5)C9—H9C0.980
C4—H41.000C10—H10A0.980
C5—C61.542 (6)C10—H10B0.980
C5—H5A0.990C10—H10C0.980
C2—C1—C8115.4 (3)C1—C6—H6A110.8
C2—C1—C799.7 (3)C5—C6—H6B110.8
C8—C1—C7118.7 (3)C1—C6—H6B110.8
C2—C1—C6104.0 (3)H6A—C6—H6B108.9
C8—C1—C6115.4 (3)C1—C7—C495.2 (3)
C7—C1—C6101.2 (3)C1—C7—H7A112.7
O1—C2—C1126.6 (3)C4—C7—H7A112.7
O1—C2—C3125.7 (3)C1—C7—H7B112.7
C1—C2—C3107.6 (3)C4—C7—H7B112.7
C10—C3—C2110.8 (3)H7A—C7—H7B110.2
C10—C3—C9108.5 (3)C1—C8—H8A109.5
C2—C3—C9109.6 (3)C1—C8—H8B109.5
C10—C3—C4115.9 (3)H8A—C8—H8B109.5
C2—C3—C4100.9 (3)C1—C8—H8C109.5
C9—C3—C4110.8 (3)H8A—C8—H8C109.5
C5—C4—C799.7 (3)H8B—C8—H8C109.5
C5—C4—C3110.5 (3)C3—C9—H9A109.5
C7—C4—C3101.8 (3)C3—C9—H9B109.5
C5—C4—H4114.4H9A—C9—H9B109.5
C7—C4—H4114.4C3—C9—H9C109.5
C3—C4—H4114.4H9A—C9—H9C109.5
C4—C5—C6102.8 (3)H9B—C9—H9C109.5
C4—C5—H5A111.2C3—C10—H10A109.5
C6—C5—H5A111.2C3—C10—H10B109.5
C4—C5—H5B111.2H10A—C10—H10B109.5
C6—C5—H5B111.2C3—C10—H10C109.5
H5A—C5—H5B109.1H10A—C10—H10C109.5
C5—C6—C1104.5 (3)H10B—C10—H10C109.5
C5—C6—H6A110.8
C8—C1—C2—O118.3 (6)C10—C3—C4—C7154.5 (3)
C7—C1—C2—O1146.6 (4)C2—C3—C4—C734.8 (3)
C6—C1—C2—O1109.2 (4)C9—C3—C4—C781.3 (3)
C8—C1—C2—C3162.7 (3)C7—C4—C5—C641.2 (3)
C7—C1—C2—C334.3 (4)C3—C4—C5—C665.4 (4)
C6—C1—C2—C369.9 (3)C4—C5—C6—C17.8 (3)
O1—C2—C3—C1055.6 (5)C2—C1—C6—C574.6 (3)
C1—C2—C3—C10123.5 (3)C8—C1—C6—C5158.0 (3)
O1—C2—C3—C964.2 (5)C7—C1—C6—C528.5 (3)
C1—C2—C3—C9116.8 (3)C2—C1—C7—C453.7 (3)
O1—C2—C3—C4178.9 (4)C8—C1—C7—C4179.8 (3)
C1—C2—C3—C40.1 (4)C6—C1—C7—C452.8 (3)
C10—C3—C4—C549.3 (4)C5—C4—C7—C158.1 (3)
C2—C3—C4—C570.4 (4)C3—C4—C7—C155.3 (3)
C9—C3—C4—C5173.5 (3)

Experimental details

Crystal data
Chemical formulaC10H16O
Mr152.23
Crystal system, space groupMonoclinic, P21
Temperature (K)150
a, b, c (Å)6.0520 (7), 10.2748 (7), 7.1621 (9)
β (°) 91.335 (4)
V3)445.24 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.15 (radius)
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.783, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
2506, 821, 757
Rint0.078
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.157, 1.10
No. of reflections821
No. of parameters103
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.22

Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996), SHELXL97.

 

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