Durenedi­methanol

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.

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

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

Crystal data

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) Å^3	Prism, colorless
Z = 8	0.38 × 0.22 × 0.22 mm
F(000) = 848

Data collection

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

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 1.83P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

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

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—C3^i	1.401 (2)	C5—H5A	0.9800
C2—C5	1.512 (2)	C5—H5B	0.9800
C3—C2^i	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—C3^i	119.93 (14)	H6A—C6—H6B	109.5
C1—C2—C5	121.24 (14)	C3—C6—H6C	109.5
C3^i—C2—C5	118.78 (15)	H6A—C6—H6C	109.5
C1—C3—C2^i	119.73 (14)	H6B—C6—H6C	109.5
C1—C3—C6	120.78 (14)	C2—C5—H5A	109.5
C2^i—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—C3^i	−2.7 (2)	C2—C1—C3—C6	−177.21 (15)
C4—C1—C2—C3^i	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—C2^i	2.7 (2)	C1—C2—C5—H5B	101.7
C4—C1—C3—C2^i	−174.80 (14)	C1—C3—C6—H6A	−107.3

Symmetry code: (i) −x+1/2, −y+3/2, −z+3/2.