Durenedimethanol (2,3,5,6-tetramethyl-1,4-phenylenedimethanol), C
12H
18O
2, crystallizes in space group
I4
1/a with a three-dimensional structure held together by O—H
O hydrogen bonds. The hydrogen bonds have a fourfold helical arrangement. The molecule lies on a crystallographic center of symmetry.
Supporting information
CCDC reference: 221668
Key indicators
- Single-crystal X-ray study
- T = 174 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.104
- Data-to-parameter ratio = 14.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
2,3,5,6-tetramethyl-1,4-phenylenedimethanol
top
Crystal data top
C12H18O2 | Dx = 1.159 Mg m−3 |
Mr = 194.26 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 3471 reflections |
Hall symbol: -I 4ad | θ = 2.5–25.0° |
a = 16.042 (4) Å | µ = 0.08 mm−1 |
c = 8.656 (2) Å | T = 174 K |
V = 2227.6 (9) Å3 | Prism, colorless |
Z = 8 | 0.38 × 0.22 × 0.22 mm |
F(000) = 848 | |
Data collection top
Siemens SMART area-detector diffractometer | 990 independent reflections |
Radiation source: fine-focus sealed tube | 871 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 25.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −19→13 |
Tmin = 0.97, Tmax = 0.98 | k = −18→19 |
5239 measured reflections | l = −10→9 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.04P)2 + 1.83P] where P = (Fo2 + 2Fc2)/3 |
990 reflections | (Δ/σ)max = 0.001 |
70 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.24536 (7) | 0.57226 (7) | 1.01908 (13) | 0.0349 (3) | |
C1 | 0.22445 (9) | 0.69735 (9) | 0.86954 (17) | 0.0273 (4) | |
C2 | 0.18753 (9) | 0.69072 (9) | 0.72350 (18) | 0.0301 (4) | |
C3 | 0.28809 (9) | 0.75530 (9) | 0.89553 (17) | 0.0285 (4) | |
C4 | 0.19336 (10) | 0.64436 (10) | 1.00204 (18) | 0.0346 (4) | |
H4A | 0.1941 | 0.6773 | 1.0987 | 0.042* | |
H4B | 0.1352 | 0.6268 | 0.9819 | 0.042* | |
C6 | 0.33110 (12) | 0.76037 (12) | 1.0506 (2) | 0.0456 (5) | |
H6A | 0.3130 | 0.8109 | 1.1046 | 0.055* | |
H6B | 0.3916 | 0.7622 | 1.0353 | 0.055* | |
H6C | 0.3166 | 0.7113 | 1.1125 | 0.055* | |
C5 | 0.12389 (13) | 0.62375 (13) | 0.6888 (3) | 0.0555 (6) | |
H5A | 0.1346 | 0.6004 | 0.5861 | 0.067* | |
H5B | 0.0678 | 0.6480 | 0.6915 | 0.067* | |
H5C | 0.1280 | 0.5795 | 0.7664 | 0.067* | |
H1 | 0.2254 (13) | 0.5450 (13) | 1.098 (3) | 0.054 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0455 (7) | 0.0308 (6) | 0.0285 (6) | 0.0067 (5) | 0.0128 (5) | 0.0084 (5) |
C1 | 0.0304 (8) | 0.0264 (7) | 0.0250 (8) | 0.0037 (6) | 0.0072 (6) | 0.0031 (6) |
C2 | 0.0304 (8) | 0.0291 (8) | 0.0307 (8) | −0.0028 (6) | 0.0007 (6) | 0.0011 (6) |
C3 | 0.0336 (8) | 0.0281 (8) | 0.0239 (8) | 0.0025 (6) | −0.0012 (6) | −0.0002 (6) |
C4 | 0.0401 (9) | 0.0335 (8) | 0.0301 (8) | 0.0069 (7) | 0.0116 (7) | 0.0074 (7) |
C6 | 0.0595 (12) | 0.0459 (10) | 0.0315 (9) | −0.0017 (9) | −0.0116 (9) | 0.0030 (8) |
C5 | 0.0557 (12) | 0.0538 (12) | 0.0568 (13) | −0.0225 (10) | −0.0116 (10) | 0.0107 (10) |
Geometric parameters (Å, º) top
O1—C4 | 1.434 (2) | C4—H4A | 0.9900 |
O1—H1 | 0.87 (2) | C4—H4B | 0.9900 |
C1—C3 | 1.399 (2) | C6—H6A | 0.9800 |
C1—C2 | 1.400 (2) | C6—H6B | 0.9800 |
C1—C4 | 1.512 (2) | C6—H6C | 0.9800 |
C2—C3i | 1.401 (2) | C5—H5A | 0.9800 |
C2—C5 | 1.512 (2) | C5—H5B | 0.9800 |
C3—C2i | 1.402 (2) | C5—H5C | 0.9800 |
C3—C6 | 1.512 (2) | | |
| | | |
C4—O1—H1 | 105.8 (13) | C1—C4—H4B | 109.7 |
C3—C1—C2 | 120.29 (13) | H4A—C4—H4B | 108.2 |
C3—C1—C4 | 119.48 (14) | C3—C6—H6A | 109.5 |
C2—C1—C4 | 120.18 (14) | C3—C6—H6B | 109.5 |
C1—C2—C3i | 119.93 (14) | H6A—C6—H6B | 109.5 |
C1—C2—C5 | 121.24 (14) | C3—C6—H6C | 109.5 |
C3i—C2—C5 | 118.78 (15) | H6A—C6—H6C | 109.5 |
C1—C3—C2i | 119.73 (14) | H6B—C6—H6C | 109.5 |
C1—C3—C6 | 120.78 (14) | C2—C5—H5A | 109.5 |
C2i—C3—C6 | 119.49 (14) | C2—C5—H5B | 109.5 |
O1—C4—C1 | 109.86 (12) | H5A—C5—H5B | 109.5 |
O1—C4—H4A | 109.7 | C2—C5—H5C | 109.5 |
C1—C4—H4A | 109.7 | H5A—C5—H5C | 109.5 |
O1—C4—H4B | 109.7 | H5B—C5—H5C | 109.5 |
| | | |
C3—C1—C2—C3i | −2.7 (2) | C2—C1—C3—C6 | −177.21 (15) |
C4—C1—C2—C3i | 174.78 (14) | C4—C1—C3—C6 | 5.3 (2) |
C3—C1—C2—C5 | 174.74 (15) | C3—C1—C4—O1 | −84.95 (17) |
C4—C1—C2—C5 | −7.8 (2) | C2—C1—C4—O1 | 97.56 (17) |
C2—C1—C3—C2i | 2.7 (2) | C1—C2—C5—H5B | 101.7 |
C4—C1—C3—C2i | −174.80 (14) | C1—C3—C6—H6A | −107.3 |
Symmetry code: (i) −x+1/2, −y+3/2, −z+3/2. |
Distances and angles (Å, °) in the O—H···O hydrogen bonds topO | H | O | O—H | O—H···O | H···O | H···O—C | C···O | Reference |
O1 | H1 | O1i | 0.87 (2) | 175 (2) | 1.85 (2) | 120 (2) | 2.717 (2) | a |
O1 | H1 | O2 | 0.90 (3) | 174 (2) | 1.82 (3) | 119 (2) | 2.714 (2) | b |
O2 | H2 | O1 | 0.92 (2) | 170 (2) | 1.81 (3) | 123 (2) | 2.725 (2) | b |
O1 | H1 | O3 | 1.07 (4) | 155 (3) | 1.75 (4) | 124 (3) | 2.757 (4) | c |
O3 | H3 | O2 | 0.97 (4) | 161 (3) | 1.84 (4) | 125 (3) | 2.779 (4) | c |
O2 | H2 | H1 | 0.97 (4) | 156 (3) | 1.93 (4) | 124 (3) | 2.848 (4) | c |
Symmetry code: (i) 3/4-y, 1/4+x, 1/4+z.
References: (a) aurenedimethanol, this work; (b) benzenedimethanol
(Shan & Jones, 2001); (c) benzenediisopropanol (Koritsánszky & Menczel,
1982). |