Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016415/cv6064sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016415/cv6064Isup2.hkl |
CCDC reference: 176009
(1S)-(-)-α-Pinene (99%) was obtained from the Aldrich Company and used without further purification. The crystal was grown in a 0.4 mm glass capillary tube at 203 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 Z (height) adjustment of the goniometer head]. The data are 90.2% complete because the crystal MELTED during an attempt to move it into a different orientation for the final set of frames. Previous attempts to reduce the temperature further for data collection resulted in the crystals being destroyed. Data were collected therefore at 203 (2) K.
H atoms were placed geometrically and refined using a riding model with an isotropic displacement parameter fixed at 1.2Ueq 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 therefore prior to merging in P212121; the reported value of Rint corresponds to merging in this space group.
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); software used to prepare material for publication: SHELXL97.
C10H16 | Dx = 1.041 Mg m−3 |
Mr = 136.23 | Mo Kα radiation, λ = 0.7107 Å |
Orthorhombic, P212121 | Cell parameters from 2466 reflections |
a = 7.1944 (6) Å | θ = 1.0–25.0° |
b = 7.5920 (3) Å | µ = 0.06 mm−1 |
c = 15.9190 (15) Å | T = 203 K |
V = 869.49 (11) Å3 | Cylinder, colourless |
Z = 4 | 0.20 mm (radius) |
F(000) = 304 |
Nonius KappaCCD diffractometer | Rint = 0.050 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 3.7° |
Thin–slice ω and ϕ scans | h = −5→8 |
3727 measured reflections | k = −7→7 |
1379 independent reflections | l = −16→18 |
1194 reflections with I > 2σ(I) |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0279P)2 + 0.1574P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
1379 reflections | Δρmax = 0.13 e Å−3 |
95 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.096 (12) |
C10H16 | V = 869.49 (11) Å3 |
Mr = 136.23 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.1944 (6) Å | µ = 0.06 mm−1 |
b = 7.5920 (3) Å | T = 203 K |
c = 15.9190 (15) Å | 0.20 mm (radius) |
Nonius KappaCCD diffractometer | 1194 reflections with I > 2σ(I) |
3727 measured reflections | Rint = 0.050 |
1379 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.13 e Å−3 |
1379 reflections | Δρmin = −0.15 e Å−3 |
95 parameters |
Experimental. Crystal grown in a 0.4 mm Lindemann tube at 203 K. Friedel pairs were merged prior to merging in P212121; the value of Rint reported corresponds to merging of the data in this space group. The absolute configuration was assigned from the known configuration of the sample. The data are only 90.2% complete because the crystal MELTED during an attempt to move it into a different orientation for the final set of frames! |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8184 (3) | −0.0414 (3) | 0.34005 (13) | 0.0381 (5) | |
H1 | 0.8467 | −0.1469 | 0.3058 | 0.046* | |
C2 | 0.7443 (3) | −0.0758 (3) | 0.42735 (12) | 0.0389 (5) | |
C3 | 0.7112 (3) | 0.0642 (3) | 0.47423 (13) | 0.0432 (6) | |
H3 | 0.6684 | 0.0501 | 0.5296 | 0.052* | |
C4 | 0.7418 (3) | 0.2465 (3) | 0.43954 (13) | 0.0434 (5) | |
H4A | 0.8282 | 0.3111 | 0.4758 | 0.052* | |
H4B | 0.6236 | 0.3107 | 0.4385 | 0.052* | |
C5 | 0.8211 (3) | 0.2352 (3) | 0.35071 (13) | 0.0397 (5) | |
H5 | 0.8524 | 0.3495 | 0.3243 | 0.048* | |
C6 | 0.7035 (3) | 0.1064 (3) | 0.29525 (12) | 0.0363 (5) | |
C7 | 0.9778 (3) | 0.0946 (3) | 0.34910 (14) | 0.0449 (5) | |
H7A | 1.0603 | 0.1021 | 0.3002 | 0.054* | |
H7B | 1.0483 | 0.0850 | 0.4016 | 0.054* | |
C8 | 0.4934 (3) | 0.1089 (3) | 0.30463 (14) | 0.0439 (5) | |
H8A | 0.4397 | 0.0156 | 0.2709 | 0.066* | |
H8B | 0.4457 | 0.2217 | 0.2859 | 0.066* | |
H8C | 0.4608 | 0.0911 | 0.3631 | 0.066* | |
C9 | 0.7516 (3) | 0.1208 (3) | 0.20215 (13) | 0.0531 (6) | |
H9A | 0.6926 | 0.0254 | 0.1717 | 0.080* | |
H9D | 0.8853 | 0.1135 | 0.1951 | 0.080* | |
H9B | 0.7075 | 0.2327 | 0.1805 | 0.080* | |
C10 | 0.7134 (4) | −0.2629 (3) | 0.45502 (15) | 0.0563 (7) | |
H10D | 0.6757 | −0.2644 | 0.5135 | 0.084* | |
H10A | 0.8278 | −0.3292 | 0.4485 | 0.084* | |
H10B | 0.6168 | −0.3159 | 0.4208 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0322 (10) | 0.0374 (12) | 0.0447 (11) | 0.0054 (8) | −0.0009 (10) | −0.0060 (9) |
C2 | 0.0323 (10) | 0.0383 (13) | 0.0461 (11) | 0.0045 (10) | −0.0050 (9) | 0.0055 (9) |
C3 | 0.0411 (11) | 0.0525 (15) | 0.0361 (10) | 0.0028 (11) | 0.0007 (9) | 0.0066 (9) |
C4 | 0.0455 (13) | 0.0395 (13) | 0.0452 (11) | −0.0026 (10) | −0.0005 (11) | −0.0066 (8) |
C5 | 0.0380 (11) | 0.0343 (11) | 0.0468 (11) | −0.0041 (9) | 0.0015 (10) | 0.0029 (9) |
C6 | 0.0347 (10) | 0.0345 (11) | 0.0396 (10) | 0.0019 (9) | −0.0009 (9) | 0.0015 (9) |
C7 | 0.0293 (9) | 0.0570 (13) | 0.0485 (12) | −0.0006 (11) | 0.0012 (9) | 0.0006 (12) |
C8 | 0.0339 (10) | 0.0456 (13) | 0.0520 (12) | 0.0018 (10) | −0.0041 (9) | 0.0022 (11) |
C9 | 0.0535 (13) | 0.0614 (15) | 0.0445 (12) | 0.0019 (13) | 0.0015 (11) | −0.0002 (11) |
C10 | 0.0542 (15) | 0.0461 (15) | 0.0685 (16) | −0.0007 (12) | −0.0062 (13) | 0.0144 (11) |
C1—C2 | 1.511 (3) | C6—C8 | 1.519 (2) |
C1—C7 | 1.549 (3) | C6—C9 | 1.526 (3) |
C1—C6 | 1.566 (3) | C7—H7A | 0.9800 |
C1—H1 | 0.9900 | C7—H7B | 0.9800 |
C2—C3 | 1.320 (3) | C8—H8A | 0.9700 |
C2—C10 | 1.504 (3) | C8—H8B | 0.9700 |
C3—C4 | 1.506 (3) | C8—H8C | 0.9700 |
C3—H3 | 0.9400 | C9—H9A | 0.9700 |
C4—C5 | 1.527 (3) | C9—H9D | 0.9700 |
C4—H4A | 0.9800 | C9—H9B | 0.9700 |
C4—H4B | 0.9800 | C10—H10D | 0.9700 |
C5—C7 | 1.553 (3) | C10—H10A | 0.9700 |
C5—C6 | 1.566 (3) | C10—H10B | 0.9700 |
C5—H5 | 0.9900 | ||
C2—C1—C7 | 106.91 (16) | C8—C6—C5 | 118.33 (17) |
C2—C1—C6 | 110.86 (15) | C9—C6—C5 | 112.36 (16) |
C7—C1—C6 | 87.46 (14) | C1—C6—C5 | 84.57 (14) |
C2—C1—H1 | 116.0 | C1—C7—C5 | 85.55 (13) |
C7—C1—H1 | 116.0 | C1—C7—H7A | 114.4 |
C6—C1—H1 | 116.0 | C5—C7—H7A | 114.4 |
C3—C2—C10 | 124.64 (19) | C1—C7—H7B | 114.4 |
C3—C2—C1 | 116.38 (17) | C5—C7—H7B | 114.4 |
C10—C2—C1 | 118.99 (18) | H7A—C7—H7B | 111.5 |
C2—C3—C4 | 120.40 (18) | C6—C8—H8A | 109.5 |
C2—C3—H3 | 119.8 | C6—C8—H8B | 109.5 |
C4—C3—H3 | 119.8 | H8A—C8—H8B | 109.5 |
C3—C4—C5 | 110.04 (16) | C6—C8—H8C | 109.5 |
C3—C4—H4A | 109.7 | H8A—C8—H8C | 109.5 |
C5—C4—H4A | 109.7 | H8B—C8—H8C | 109.5 |
C3—C4—H4B | 109.7 | C6—C9—H9A | 109.5 |
C5—C4—H4B | 109.7 | C6—C9—H9D | 109.5 |
H4A—C4—H4B | 108.2 | H9A—C9—H9D | 109.5 |
C4—C5—C7 | 108.97 (17) | C6—C9—H9B | 109.5 |
C4—C5—C6 | 110.80 (16) | H9A—C9—H9B | 109.5 |
C7—C5—C6 | 87.34 (15) | H9D—C9—H9B | 109.5 |
C4—C5—H5 | 115.5 | C2—C10—H10D | 109.5 |
C7—C5—H5 | 115.5 | C2—C10—H10A | 109.5 |
C6—C5—H5 | 115.5 | H10D—C10—H10A | 109.5 |
C8—C6—C9 | 108.69 (17) | C2—C10—H10B | 109.5 |
C8—C6—C1 | 119.33 (17) | H10D—C10—H10B | 109.5 |
C9—C6—C1 | 111.94 (16) | H10A—C10—H10B | 109.5 |
C7—C1—C2—C3 | 47.0 (2) | C2—C1—C6—C5 | 78.47 (17) |
C6—C1—C2—C3 | −46.8 (2) | C7—C1—C6—C5 | −28.68 (14) |
C7—C1—C2—C10 | −133.0 (2) | C4—C5—C6—C8 | 39.8 (2) |
C6—C1—C2—C10 | 133.23 (19) | C7—C5—C6—C8 | 149.11 (18) |
C10—C2—C3—C4 | −178.2 (2) | C4—C5—C6—C9 | 167.80 (17) |
C1—C2—C3—C4 | 1.8 (3) | C7—C5—C6—C9 | −82.91 (18) |
C2—C3—C4—C5 | −3.1 (3) | C4—C5—C6—C1 | −80.69 (17) |
C3—C4—C5—C7 | −44.7 (2) | C7—C5—C6—C1 | 28.61 (14) |
C3—C4—C5—C6 | 49.7 (2) | C2—C1—C7—C5 | −82.15 (17) |
C2—C1—C6—C8 | −41.1 (2) | C6—C1—C7—C5 | 28.89 (14) |
C7—C1—C6—C8 | −148.23 (18) | C4—C5—C7—C1 | 82.21 (17) |
C2—C1—C6—C9 | −169.60 (16) | C6—C5—C7—C1 | −28.89 (14) |
C7—C1—C6—C9 | 83.26 (18) |
Experimental details
Crystal data | |
Chemical formula | C10H16 |
Mr | 136.23 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 203 |
a, b, c (Å) | 7.1944 (6), 7.5920 (3), 15.9190 (15) |
V (Å3) | 869.49 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.20 (radius) |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3727, 1379, 1194 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.103, 1.06 |
No. of reflections | 1379 |
No. of parameters | 95 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.15 |
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), SHELXL97.
α-Pinene, (I), is very widely distributed in nature. It is present in the majority of essential oils derived from the Coniferae and it is the principal constituent of oil of turpentine. 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)].