(1S*,2S*)-1,2-Di-tert-butyl­glycol

Kerscher, T.; Betz, R.; Klüfers, P.; Mayer, P.

doi:10.1107/S1600536808043560

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o211

doi:10.1107/S1600536808043560

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(1S,2S)-1,2-Di-tert-butylglycol

Tobias Kerscher,^a Richard Betz,^a Peter Klüfers ^a ^* and Peter Mayer ^a

^aLudwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5–13 (Haus D), 81377 München, Germany
^*Correspondence e-mail: kluef@cup.uni-muenchen.de

(Received 28 November 2008; accepted 22 December 2008; online 24 December 2008)

In the crystal structure of the title compound, C₁₀H₂₂O₂, co-operative chains of O—H⋯O hydrogen bonds are established by intra- as well as intermolecular interactions. These hydrogen bonds connect the molecules into infinite strands along [100], with a binary level graph-set descriptor C₂²(4). Excluding the H atoms on the hydroxy groups, the molecule shows non-crystallographic C₂ symmetry.

Related literature

The compound was synthesized according to a published procedure (Boehrer et al., 1997 ). For the crystal structures of other ethane-1,2-diol derivatives with bulky substituents, see: Betz & Klüfers (2007 ); Allscher et al. (2008 ). For graph-set descriptors, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₀H₂₂O₂
M_r = 174.28
Orthorhombic, P 2₁ 2₁ 2
a = 9.7799 (3) Å
b = 16.3879 (7) Å
c = 6.9771 (3) Å
V = 1118.23 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 200 (2) K
0.30 × 0.09 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
8640 measured reflections
1490 independent reflections
1253 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.05
1490 reflections
117 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H811⋯O2ⁱ	0.84	1.93	2.7721 (16)	176
O2—H821⋯O1	0.84	1.97	2.5129 (16)	121
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: COLLECT (Nonius, 2004 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043560/bi2332sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043560/bi2332Isup2.hkl

checkCIF report

Comment top

The title compound was synthesized as a potential chelating ligand with sterically demanding substituents on the carbon backbone to estimate the influence of steric pretense on coordination reactions with different central atoms.

In the molecule (Fig. 1) bond lengths and angles are found in the range apparent for other vicinal diols bearing sterically more demanding substituents (Betz & Klüfers, 2007, Allscher et al., 2008). While the tert-butyl groups adopt a staggered conformation with respect to the hydroxy groups, the O atoms are present in a nearly eclipsed arrangement. The reason for this unfavourable conformation becomes evident when examining intermolecular contacts.

In the crystal structure, inter- and intramolecular hydrogen bonds are present which connect the molecules into strands along [1 0 0] (Fig. 2). The bulky hydrophobic tert-butyl groups encase this strand of hydroxyl groups. The hydrogen bonds form cooperative chains. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995) the descriptor for these chains on the binary level is C²₂(4).

Excluding the H atoms on the hydroxy groups, the molecule shows non-crystallographic C₂ symmetry.

The molecular packing of the title compound is shown in Figure 3.

Related literature top

The compound was synthesized according to a published procedure (Boehrer et al., 1997). For the crystal structures of other ethane-1,2-diol derivatives with bulky substituents, see: Betz & Klüfers (2007); Allscher et al. (2008). For graph-set descriptors, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

The title compound was prepared according to a published procedure (Boehrer et al., 1997). Crystals suitable for X-ray studies were obtained upon recrystallization from boiling toluene.

Computing details top

Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. Hydrogen bonds in the crystal structure of the title compound, viewed along [0 0 1]. Underlying hydrogen bonds are not illustrated for clarity. Symmetry codes: ⁱx + 1/2, -y + 1/2, -z + 2; ⁱⁱx - 1/2, -y + 1/2, -z + 2.
	Fig. 3. The packing of the title compound, viewed along [0 0 - 1].

(1S*,2S*)-1,2-Di-tert-butylglycol top

Crystal data top

C₁₀H₂₂O₂	F(000) = 392
M_r = 174.28	D_x = 1.035 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 13560 reflections
a = 9.7799 (3) Å	θ = 3.1–27.5°
b = 16.3879 (7) Å	µ = 0.07 mm⁻¹
c = 6.9771 (3) Å	T = 200 K
V = 1118.23 (8) Å³	Rod, colourless
Z = 4	0.30 × 0.09 × 0.02 mm

Data collection top

Nonius KappaCCD diffractometer	1253 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.040
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 27.5°, θ_min = 3.2°
CCD; rotation images; thick slices scans	h = −12→11
8640 measured reflections	k = −19→21
1490 independent reflections	l = −9→8

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0621P)² + 0.0637P] where P = (F_o² + 2F_c²)/3
1490 reflections	(Δ/σ)_max < 0.001
117 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₀H₂₂O₂	V = 1118.23 (8) Å³
M_r = 174.28	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 9.7799 (3) Å	µ = 0.07 mm⁻¹
b = 16.3879 (7) Å	T = 200 K
c = 6.9771 (3) Å	0.30 × 0.09 × 0.02 mm

Data collection top

Nonius KappaCCD diffractometer	1253 reflections with I > 2σ(I)
8640 measured reflections	R_int = 0.040
1490 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
1490 reflections	Δρ_min = −0.15 e Å⁻³
117 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.13030 (11)	0.30082 (8)	0.96003 (18)	0.0402 (3)
H811	0.0476	0.2922	0.9857	0.060*
O2	0.35411 (12)	0.22582 (8)	0.9762 (2)	0.0437 (4)
H821	0.3054	0.2548	1.0484	0.066*
C1	0.16231 (16)	0.26595 (10)	0.7782 (2)	0.0330 (4)
H1	0.0792	0.2371	0.7292	0.040*
C2	0.27611 (16)	0.20174 (10)	0.8121 (2)	0.0332 (4)
H2	0.3386	0.2035	0.6988	0.040*
C3	0.19990 (19)	0.33399 (11)	0.6353 (3)	0.0393 (4)
C4	0.0811 (2)	0.39538 (13)	0.6286 (3)	0.0551 (6)
H41	0.0731	0.4228	0.7530	0.083*
H42	−0.0042	0.3665	0.6001	0.083*
H43	0.0987	0.4360	0.5285	0.083*
C5	0.2176 (3)	0.29796 (15)	0.4358 (3)	0.0628 (6)
H51	0.2281	0.3422	0.3424	0.094*
H52	0.1370	0.2653	0.4031	0.094*
H53	0.2992	0.2632	0.4335	0.094*
C6	0.3298 (2)	0.37869 (13)	0.6961 (3)	0.0516 (5)
H61	0.4075	0.3409	0.6917	0.077*
H62	0.3188	0.3994	0.8270	0.077*
H63	0.3466	0.4244	0.6087	0.077*
C7	0.22584 (18)	0.11294 (12)	0.8338 (3)	0.0409 (5)
C8	0.1634 (3)	0.08512 (14)	0.6441 (4)	0.0687 (7)
H81	0.2274	0.0967	0.5394	0.103*
H82	0.0776	0.1145	0.6218	0.103*
H83	0.1453	0.0264	0.6494	0.103*
C9	0.1230 (2)	0.10514 (15)	0.9965 (4)	0.0656 (7)
H91	0.0986	0.0476	1.0138	0.098*
H92	0.0407	0.1366	0.9653	0.098*
H93	0.1634	0.1262	1.1150	0.098*
C10	0.3495 (2)	0.05872 (12)	0.8749 (4)	0.0542 (5)
H101	0.3896	0.0740	0.9985	0.081*
H102	0.4176	0.0658	0.7733	0.081*
H103	0.3204	0.0015	0.8793	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0321 (6)	0.0536 (8)	0.0349 (6)	0.0056 (6)	0.0041 (5)	−0.0067 (6)
O2	0.0344 (6)	0.0518 (8)	0.0448 (7)	0.0046 (5)	−0.0136 (6)	−0.0073 (6)
C1	0.0260 (7)	0.0416 (9)	0.0314 (8)	0.0013 (7)	−0.0020 (7)	−0.0047 (7)
C2	0.0251 (7)	0.0428 (9)	0.0317 (8)	0.0007 (7)	−0.0004 (6)	−0.0032 (7)
C3	0.0397 (9)	0.0446 (10)	0.0334 (9)	0.0051 (8)	−0.0020 (8)	0.0026 (8)
C4	0.0548 (11)	0.0537 (12)	0.0568 (12)	0.0140 (10)	−0.0059 (11)	0.0094 (11)
C5	0.0841 (15)	0.0716 (15)	0.0327 (10)	0.0129 (13)	0.0028 (10)	0.0025 (10)
C6	0.0452 (11)	0.0493 (11)	0.0602 (13)	−0.0051 (9)	0.0029 (10)	0.0121 (10)
C7	0.0341 (9)	0.0374 (9)	0.0513 (11)	0.0025 (7)	0.0012 (8)	−0.0015 (8)
C8	0.0733 (15)	0.0485 (12)	0.0843 (18)	−0.0004 (12)	−0.0263 (14)	−0.0208 (12)
C9	0.0580 (13)	0.0499 (12)	0.0889 (18)	−0.0016 (10)	0.0295 (12)	0.0095 (12)
C10	0.0463 (10)	0.0435 (11)	0.0729 (14)	0.0087 (9)	−0.0010 (11)	0.0023 (11)

Geometric parameters (Å, º) top

O1—C1	1.426 (2)	C5—H53	0.980
O1—H811	0.840	C6—H61	0.980
O2—C2	1.431 (2)	C6—H62	0.980
O2—H821	0.840	C6—H63	0.980
C1—C3	1.540 (3)	C7—C9	1.522 (3)
C1—C2	1.550 (2)	C7—C8	1.527 (3)
C1—H1	1.000	C7—C10	1.528 (3)
C2—C7	1.543 (3)	C8—H81	0.980
C2—H2	1.000	C8—H82	0.980
C3—C5	1.522 (3)	C8—H83	0.980
C3—C6	1.527 (3)	C9—H91	0.980
C3—C4	1.538 (2)	C9—H92	0.980
C4—H41	0.980	C9—H93	0.980
C4—H42	0.980	C10—H101	0.980
C4—H43	0.980	C10—H102	0.980
C5—H51	0.980	C10—H103	0.980
C5—H52	0.980

C1—O1—H811	109.5	H52—C5—H53	109.5
C2—O2—H821	109.5	C3—C6—H61	109.5
O1—C1—C3	109.77 (14)	C3—C6—H62	109.5
O1—C1—C2	107.08 (13)	H61—C6—H62	109.5
C3—C1—C2	114.77 (13)	C3—C6—H63	109.5
O1—C1—H1	108.3	H61—C6—H63	109.5
C3—C1—H1	108.3	H62—C6—H63	109.5
C2—C1—H1	108.3	C9—C7—C8	110.91 (18)
O2—C2—C7	110.58 (14)	C9—C7—C10	109.53 (17)
O2—C2—C1	108.52 (13)	C8—C7—C10	107.79 (17)
C7—C2—C1	115.24 (14)	C9—C7—C2	111.26 (16)
O2—C2—H2	107.4	C8—C7—C2	108.91 (16)
C7—C2—H2	107.4	C10—C7—C2	108.35 (14)
C1—C2—H2	107.4	C7—C8—H81	109.5
C5—C3—C6	110.22 (19)	C7—C8—H82	109.5
C5—C3—C4	108.20 (17)	H81—C8—H82	109.5
C6—C3—C4	108.86 (16)	C7—C8—H83	109.5
C5—C3—C1	109.78 (16)	H81—C8—H83	109.5
C6—C3—C1	111.47 (15)	H82—C8—H83	109.5
C4—C3—C1	108.22 (14)	C7—C9—H91	109.5
C3—C4—H41	109.5	C7—C9—H92	109.5
C3—C4—H42	109.5	H91—C9—H92	109.5
H41—C4—H42	109.5	C7—C9—H93	109.5
C3—C4—H43	109.5	H91—C9—H93	109.5
H41—C4—H43	109.5	H92—C9—H93	109.5
H42—C4—H43	109.5	C7—C10—H101	109.5
C3—C5—H51	109.5	C7—C10—H102	109.5
C3—C5—H52	109.5	H101—C10—H102	109.5
H51—C5—H52	109.5	C7—C10—H103	109.5
C3—C5—H53	109.5	H101—C10—H103	109.5
H51—C5—H53	109.5	H102—C10—H103	109.5

O1—C1—C2—O2	−28.26 (17)	O1—C1—C3—C4	−55.45 (18)
C3—C1—C2—O2	93.86 (17)	C2—C1—C3—C4	−176.09 (15)
O1—C1—C2—C7	96.34 (17)	O2—C2—C7—C9	66.46 (19)
C3—C1—C2—C7	−141.55 (15)	C1—C2—C7—C9	−57.1 (2)
O1—C1—C3—C5	−173.34 (16)	O2—C2—C7—C8	−170.99 (15)
C2—C1—C3—C5	66.0 (2)	C1—C2—C7—C8	65.5 (2)
O1—C1—C3—C6	64.23 (18)	O2—C2—C7—C10	−54.00 (19)
C2—C1—C3—C6	−56.4 (2)	C1—C2—C7—C10	−177.51 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H811···O2ⁱ	0.84	1.93	2.7721 (16)	176
O2—H821···O1	0.84	1.97	2.5129 (16)	121

Symmetry code: (i) x−1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₀H₂₂O₂
M_r	174.28
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	200
a, b, c (Å)	9.7799 (3), 16.3879 (7), 6.9771 (3)
V (Å³)	1118.23 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.09 × 0.02

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8640, 1490, 1253
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.05
No. of reflections	1490
No. of parameters	117
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: COLLECT (Nonius, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H811···O2ⁱ	0.84	1.93	2.7721 (16)	175.5
O2—H821···O1	0.84	1.97	2.5129 (16)	121.4

Symmetry code: (i) x−1/2, −y+1/2, −z+2.

Acknowledgements

TK thanks the Hanns-Seidel-Stiftung for a PhD scholarship financed by the Bundesministerium für Bildung und Forschung.

References

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