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Durenedi­methanol (2,3,5,6-tetra­methyl-1,4-phenyl­enedi­meth­anol), C12H18O2, crystallizes in space group I41/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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014223/om6152sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014223/om6152Isup2.hkl
Contains datablock I

CCDC reference: 221668

Key indicators

  • Single-crystal X-ray study
  • T = 174 K
  • Mean [sigma](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








Computing details top

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
C12H18O2Dx = 1.159 Mg m3
Mr = 194.26Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 3471 reflections
Hall symbol: -I 4adθ = 2.5–25.0°
a = 16.042 (4) ŵ = 0.08 mm1
c = 8.656 (2) ÅT = 174 K
V = 2227.6 (9) Å3Prism, colorless
Z = 80.38 × 0.22 × 0.22 mm
F(000) = 848
Data collection top
Siemens SMART area-detector
diffractometer
990 independent reflections
Radiation source: fine-focus sealed tube871 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 1913
Tmin = 0.97, Tmax = 0.98k = 1819
5239 measured reflectionsl = 109
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H 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 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.24536 (7)0.57226 (7)1.01908 (13)0.0349 (3)
C10.22445 (9)0.69735 (9)0.86954 (17)0.0273 (4)
C20.18753 (9)0.69072 (9)0.72350 (18)0.0301 (4)
C30.28809 (9)0.75530 (9)0.89553 (17)0.0285 (4)
C40.19336 (10)0.64436 (10)1.00204 (18)0.0346 (4)
H4A0.19410.67731.09870.042*
H4B0.13520.62680.98190.042*
C60.33110 (12)0.76037 (12)1.0506 (2)0.0456 (5)
H6A0.31300.81091.10460.055*
H6B0.39160.76221.03530.055*
H6C0.31660.71131.11250.055*
C50.12389 (13)0.62375 (13)0.6888 (3)0.0555 (6)
H5A0.13460.60040.58610.067*
H5B0.06780.64800.69150.067*
H5C0.12800.57950.76640.067*
H10.2254 (13)0.5450 (13)1.098 (3)0.054 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0455 (7)0.0308 (6)0.0285 (6)0.0067 (5)0.0128 (5)0.0084 (5)
C10.0304 (8)0.0264 (7)0.0250 (8)0.0037 (6)0.0072 (6)0.0031 (6)
C20.0304 (8)0.0291 (8)0.0307 (8)0.0028 (6)0.0007 (6)0.0011 (6)
C30.0336 (8)0.0281 (8)0.0239 (8)0.0025 (6)0.0012 (6)0.0002 (6)
C40.0401 (9)0.0335 (8)0.0301 (8)0.0069 (7)0.0116 (7)0.0074 (7)
C60.0595 (12)0.0459 (10)0.0315 (9)0.0017 (9)0.0116 (9)0.0030 (8)
C50.0557 (12)0.0538 (12)0.0568 (13)0.0225 (10)0.0116 (10)0.0107 (10)
Geometric parameters (Å, º) top
O1—C41.434 (2)C4—H4A0.9900
O1—H10.87 (2)C4—H4B0.9900
C1—C31.399 (2)C6—H6A0.9800
C1—C21.400 (2)C6—H6B0.9800
C1—C41.512 (2)C6—H6C0.9800
C2—C3i1.401 (2)C5—H5A0.9800
C2—C51.512 (2)C5—H5B0.9800
C3—C2i1.402 (2)C5—H5C0.9800
C3—C61.512 (2)
C4—O1—H1105.8 (13)C1—C4—H4B109.7
C3—C1—C2120.29 (13)H4A—C4—H4B108.2
C3—C1—C4119.48 (14)C3—C6—H6A109.5
C2—C1—C4120.18 (14)C3—C6—H6B109.5
C1—C2—C3i119.93 (14)H6A—C6—H6B109.5
C1—C2—C5121.24 (14)C3—C6—H6C109.5
C3i—C2—C5118.78 (15)H6A—C6—H6C109.5
C1—C3—C2i119.73 (14)H6B—C6—H6C109.5
C1—C3—C6120.78 (14)C2—C5—H5A109.5
C2i—C3—C6119.49 (14)C2—C5—H5B109.5
O1—C4—C1109.86 (12)H5A—C5—H5B109.5
O1—C4—H4A109.7C2—C5—H5C109.5
C1—C4—H4A109.7H5A—C5—H5C109.5
O1—C4—H4B109.7H5B—C5—H5C109.5
C3—C1—C2—C3i2.7 (2)C2—C1—C3—C6177.21 (15)
C4—C1—C2—C3i174.78 (14)C4—C1—C3—C65.3 (2)
C3—C1—C2—C5174.74 (15)C3—C1—C4—O184.95 (17)
C4—C1—C2—C57.8 (2)C2—C1—C4—O197.56 (17)
C2—C1—C3—C2i2.7 (2)C1—C2—C5—H5B101.7
C4—C1—C3—C2i174.80 (14)C1—C3—C6—H6A107.3
Symmetry code: (i) x+1/2, y+3/2, z+3/2.
Distances and angles (Å, °) in the O—H···O hydrogen bonds top
OHOO—HO—H···OH···OH···O—CC···OReference
O1H1O1i0.87 (2)175 (2)1.85 (2)120 (2)2.717 (2)a
O1H1O20.90 (3)174 (2)1.82 (3)119 (2)2.714 (2)b
O2H2O10.92 (2)170 (2)1.81 (3)123 (2)2.725 (2)b
O1H1O31.07 (4)155 (3)1.75 (4)124 (3)2.757 (4)c
O3H3O20.97 (4)161 (3)1.84 (4)125 (3)2.779 (4)c
O2H2H10.97 (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).
 

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