(1S*,2S*)-1,2-Di-tert-butyl­glycol

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.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.109
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               1490
           Count of symmetry unique reflns         1500
           Completeness (_total/calc)             99.33%
           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
PLAT791_ALERT_4_G The Model has Chirality at C1      (Verify) ....          S
PLAT791_ALERT_4_G The Model has Chirality at C2      (Verify) ....          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

Due to the absence of a strong anomalous scatterer, the absolute structure parameter, which is 0.982 with an estimated standard deviation of 1.241 for the unmerged data set, is meaningless. Thus 1056 Friedel opposites have been merged and the absolute configuration has been arbitrarily chosen.

Carbon-bound as well as oxygen-bound H atoms were placed in calculated positions (C—H 1.00 Å for CH-groups, C—H 0.98 Å for methyl groups and O—H 0.84 Å for hydroxy groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C) for the CH-groups and 1.5U_eq(C) for methyl groups and 1.5U_eq(O) for the hydroxy groups.

Computing details

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

	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

Crystal data

C10H22O2	F(000) = 392
Mr = 174.28	Dx = 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) Å^3	Rod, colourless
Z = 4	0.30 × 0.09 × 0.02 mm

Data collection

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

Refinement

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H811···O2^i	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.