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The crystal structure of (1S)-(−)-β-pinene, C10H16, has been determined at 185 (2) K by in situ growth from the liquid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016427/cv6065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016427/cv6065Isup2.hkl
Contains datablock I

CCDC reference: 176010

Key indicators

  • Single-crystal X-ray study
  • T = 185 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.060
  • wR factor = 0.155
  • Data-to-parameter ratio = 18.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.78 From the CIF: _reflns_number_total 1747 Count of symmetry unique reflns 1100 Completeness (_total/calc) 158.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 647 Fraction of Friedel pairs measured 0.588 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.

Comment top

β-Pinene, (I), occurs in nature in the majority of the oils in which α-pinene is found; the percentage present however is very variable and is, as a rule, considerably less than that of the latter. For an account of the history of β-pinene and the determination of its structure using the techniques of classical organic chemistry, see 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

(1S)-(-)-β-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 201 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 crystal was cooled subsequently to 185 (2) K for data collection.

Refinement top

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.

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); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The asymmetric unit in (I) showing displacement ellipsoids at the 50% probability level (XP; Sheldrick, 1993).
[Figure 2] Fig. 2. Projection onto (100) of the crystal structure of (I) (CAMERON; Watkin et al., 1996).
(1S)-(-)-β-Pinene top
Crystal data top
C10H16Dx = 1.034 Mg m3
Mr = 136.23Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, P212121Cell parameters from 3825 reflections
a = 7.5079 (3) Åθ = 1.0–26.7°
b = 9.3361 (8) ŵ = 0.06 mm1
c = 12.4875 (11) ÅT = 185 K
V = 875.30 (11) Å3Cylinder, colourless
Z = 40.20 mm (radius)
F(000) = 304
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.081
Radiation source: fine-focus sealed tubeθmax = 26.8°, θmin = 3.9°
Thin–slice ω and ϕ scansh = 99
4164 measured reflectionsk = 1111
1747 independent reflectionsl = 1515
1498 reflections with I > 2σ(I)
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0527P)2 + 0.2821P]
where P = (Fo2 + 2Fc2)/3
1747 reflections(Δ/σ)max = 0.004
93 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C10H16V = 875.30 (11) Å3
Mr = 136.23Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.5079 (3) ŵ = 0.06 mm1
b = 9.3361 (8) ÅT = 185 K
c = 12.4875 (11) Å0.20 mm (radius)
Data collection top
Nonius KappaCCD
diffractometer
1498 reflections with I > 2σ(I)
4164 measured reflectionsRint = 0.081
1747 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.09Δρmax = 0.23 e Å3
1747 reflectionsΔρmin = 0.20 e Å3
93 parameters
Special details top

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.

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
C10.8191 (3)0.1927 (2)0.77499 (17)0.0373 (5)
H10.83110.09720.73960.045*
C20.7957 (3)0.1898 (2)0.89424 (17)0.0375 (5)
C30.8058 (4)0.3355 (2)0.94799 (19)0.0468 (6)
H3A0.91980.34230.98760.056*
H3B0.70800.34311.00090.056*
C40.7930 (4)0.4633 (2)0.86954 (19)0.0480 (6)
H4A0.67550.51010.87810.058*
H4B0.88590.53440.88780.058*
C50.8159 (3)0.4177 (2)0.75372 (18)0.0418 (5)
H50.82540.49790.70090.050*
C60.6809 (3)0.2971 (2)0.72334 (16)0.0365 (5)
C70.9645 (3)0.3039 (3)0.7468 (2)0.0477 (6)
H7A1.05860.31420.80180.057*
H7B1.01620.29220.67440.057*
C80.4944 (3)0.3017 (3)0.77088 (19)0.0505 (6)
H8B0.43080.21340.75260.076*
H8C0.42980.38420.74180.076*
H8D0.50250.31060.84890.076*
C90.6662 (4)0.2773 (3)0.60259 (19)0.0557 (7)
H9B0.60540.18670.58720.084*
H9C0.78580.27550.57110.084*
H9D0.59810.35680.57190.084*
C100.7721 (4)0.0701 (3)0.9487 (2)0.0482 (6)
H10B0.76930.01920.91230.072*
H10C0.75780.07331.02420.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0373 (10)0.0307 (9)0.0439 (12)0.0025 (10)0.0046 (9)0.0010 (9)
C20.0309 (10)0.0384 (10)0.0433 (11)0.0020 (9)0.0042 (8)0.0034 (9)
C30.0561 (14)0.0482 (14)0.0362 (12)0.0005 (12)0.0059 (11)0.0002 (9)
C40.0619 (16)0.0368 (11)0.0452 (14)0.0034 (11)0.0035 (11)0.0050 (9)
C50.0480 (13)0.0346 (10)0.0428 (12)0.0009 (10)0.0044 (11)0.0043 (9)
C60.0391 (11)0.0382 (10)0.0321 (10)0.0007 (10)0.0014 (8)0.0003 (9)
C70.0374 (12)0.0502 (14)0.0555 (14)0.0026 (10)0.0107 (10)0.0004 (13)
C80.0386 (12)0.0696 (17)0.0435 (13)0.0054 (13)0.0017 (9)0.0025 (13)
C90.0717 (18)0.0591 (15)0.0363 (12)0.0023 (15)0.0015 (12)0.0010 (10)
C100.0533 (15)0.0446 (12)0.0468 (13)0.0030 (11)0.0080 (11)0.0082 (11)
Geometric parameters (Å, º) top
C1—C21.500 (3)C5—H51.0000
C1—C71.547 (3)C6—C81.521 (3)
C1—C61.562 (3)C6—C91.523 (3)
C1—H11.0000C7—H7A0.9900
C2—C101.320 (3)C7—H7B0.9900
C2—C31.519 (3)C8—H8B0.9800
C3—C41.547 (3)C8—H8C0.9800
C3—H3A0.9900C8—H8D0.9800
C3—H3B0.9900C9—H9B0.9800
C4—C51.517 (3)C9—H9C0.9800
C4—H4A0.9900C9—H9D0.9800
C4—H4B0.9900C10—H10B0.9500
C5—C71.543 (3)C10—H10C0.9500
C5—C61.562 (3)
C2—C1—C7108.72 (19)C8—C6—C9108.85 (19)
C2—C1—C6110.10 (16)C8—C6—C1117.88 (18)
C7—C1—C687.48 (15)C9—C6—C1112.40 (18)
C2—C1—H1115.7C8—C6—C5118.79 (19)
C7—C1—H1115.7C9—C6—C5112.03 (19)
C6—C1—H1115.7C1—C6—C585.34 (15)
C10—C2—C1122.8 (2)C5—C7—C186.49 (15)
C10—C2—C3122.5 (2)C5—C7—H7A114.2
C1—C2—C3114.62 (19)C1—C7—H7A114.2
C2—C3—C4114.06 (19)C5—C7—H7B114.2
C2—C3—H3A108.7C1—C7—H7B114.2
C4—C3—H3A108.7H7A—C7—H7B111.4
C2—C3—H3B108.7C6—C8—H8B109.5
C4—C3—H3B108.7C6—C8—H8C109.5
H3A—C3—H3B107.6H8B—C8—H8C109.5
C5—C4—C3112.37 (19)C6—C8—H8D109.5
C5—C4—H4A109.1H8B—C8—H8D109.5
C3—C4—H4A109.1H8C—C8—H8D109.5
C5—C4—H4B109.1C6—C9—H9B109.5
C3—C4—H4B109.1C6—C9—H9C109.5
H4A—C4—H4B107.9H9B—C9—H9C109.5
C4—C5—C7109.2 (2)C6—C9—H9D109.5
C4—C5—C6111.11 (19)H9B—C9—H9D109.5
C7—C5—C687.65 (16)H9C—C9—H9D109.5
C4—C5—H5115.2C2—C10—H10B120.0
C7—C5—H5115.2C2—C10—H10C120.0
C6—C5—H5115.2H10B—C10—H10C120.0
C7—C1—C2—C10139.6 (2)C2—C1—C6—C582.37 (18)
C6—C1—C2—C10126.1 (2)C7—C1—C6—C526.65 (16)
C7—C1—C2—C339.0 (2)C4—C5—C6—C836.4 (3)
C6—C1—C2—C355.3 (2)C7—C5—C6—C8146.1 (2)
C10—C2—C3—C4167.5 (2)C4—C5—C6—C9164.8 (2)
C1—C2—C3—C414.0 (3)C7—C5—C6—C985.6 (2)
C2—C3—C4—C513.3 (3)C4—C5—C6—C182.9 (2)
C3—C4—C5—C740.4 (3)C7—C5—C6—C126.72 (15)
C3—C4—C5—C654.7 (3)C4—C5—C7—C184.6 (2)
C2—C1—C6—C837.9 (3)C6—C5—C7—C126.96 (15)
C7—C1—C6—C8146.9 (2)C2—C1—C7—C583.43 (18)
C2—C1—C6—C9165.7 (2)C6—C1—C7—C526.95 (16)
C7—C1—C6—C985.3 (2)

Experimental details

Crystal data
Chemical formulaC10H16
Mr136.23
Crystal system, space groupOrthorhombic, P212121
Temperature (K)185
a, b, c (Å)7.5079 (3), 9.3361 (8), 12.4875 (11)
V3)875.30 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.06
Crystal size (mm)0.20 (radius)
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4164, 1747, 1498
Rint0.081
(sin θ/λ)max1)0.634
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.155, 1.09
No. of reflections1747
No. of parameters93
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.20

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.

 

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