2,4,6-Tri­methyl­phenol

Crystals of the title compound, C₉H₁₂O, were formed as an unexpected by-product during the recrystallization of (2R,3R)-[alpha],[alpha],[alpha]',[alpha]'-tetramesityl-1,4-dioxa­spiro­[4,5]­decane-2,3-di­methanol from hexane/ethyl acetate (7:3). Strong hydrogen bonds between hydroxide groups connect the mol­ecules around one set of four symmetry-equivalent 2₁ axes.

Computing details

Data collection: IPDS2.87 (Stoe & Cie, 1997); cell refinement: IPDS2.87; data reduction: IPDS2.87; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Trimethylphenol

Crystal data

C9H12O	F(000) = 296
Mr = 136.19	Dx = 1.155 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.575 (3) Å	Cell parameters from 2000 reflections
b = 4.3655 (6) Å	θ = 5.0–20.0°
c = 15.647 (4) Å	µ = 0.07 mm^−1
β = 97.94 (3)°	T = 180 K
V = 783.1 (3) Å^3	Prism, colourless
Z = 4	0.60 × 0.20 × 0.20 mm

Data collection

Stoe IPDS diffractometer	1063 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.028
Planar graphite monochromator	θmax = 25.7°, θmin = 3.0°
Detector resolution: 6.667 pixels mm^-1	h = −14→14
φ–rotation, φ–incr. = 1.5°, 153 exposures scans	k = −4→4
4975 measured reflections	l = −19→19
1412 independent reflections

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.108	All H-atom parameters refined
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0742P)^2] where P = (Fo^2 + 2Fc^2)/3
1412 reflections	(Δ/σ)max = 0.003
139 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

Special details

Experimental. Recrystallized from tetrahydrofuran. During data collection the crystal was in cold N₂ gas of the Cryostream Cooler (Oxford Cryosystems, 1992) mounted on a φ-axis diffractometer supplied with an area detector.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.83193 (11)	0.0183 (3)	0.27937 (8)	0.0244 (3)
C2	0.82592 (12)	0.1022 (3)	0.36469 (8)	0.0266 (4)
C3	0.91816 (14)	0.2965 (4)	0.41457 (10)	0.0347 (4)
H3A	0.9287 (16)	0.490 (5)	0.3858 (12)	0.060 (6)*
H3B	0.8970 (16)	0.334 (4)	0.4708 (13)	0.055 (5)*
H3C	0.993 (2)	0.195 (5)	0.4194 (13)	0.066 (6)*
C4	0.73194 (12)	−0.0049 (4)	0.40219 (8)	0.0294 (4)
H4	0.7281 (12)	0.051 (4)	0.4627 (10)	0.033 (4)*
C5	0.64616 (12)	−0.1896 (4)	0.35892 (9)	0.0302 (4)
C6	0.54756 (16)	−0.3111 (5)	0.40250 (12)	0.0429 (5)
H6A	0.518 (3)	−0.158 (8)	0.4397 (19)	0.112 (9)*
H6B	0.569 (2)	−0.474 (7)	0.4371 (18)	0.108 (10)*
H6C	0.482 (2)	−0.349 (6)	0.3619 (17)	0.090 (8)*
C7	0.65560 (13)	−0.2666 (4)	0.27391 (9)	0.0313 (4)
H7	0.5967 (14)	−0.392 (4)	0.2441 (10)	0.033 (4)*
C8	0.74717 (12)	−0.1652 (4)	0.23288 (8)	0.0284 (4)
C9	0.75525 (16)	−0.2526 (5)	0.14077 (9)	0.0393 (5)
H9A	0.683 (2)	−0.342 (5)	0.1138 (13)	0.070 (6)*
H9B	0.8180 (19)	−0.393 (5)	0.1361 (12)	0.065 (6)*
H9C	0.7733 (17)	−0.079 (6)	0.1080 (13)	0.069 (6)*
O1	0.92452 (8)	0.1055 (3)	0.23730 (6)	0.0301 (3)
H1Y	0.9620 (17)	0.269 (5)	0.2610 (13)	0.057 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0240 (7)	0.0241 (9)	0.0259 (7)	0.0040 (6)	0.0066 (5)	0.0039 (6)
C2	0.0300 (7)	0.0246 (9)	0.0248 (7)	0.0048 (6)	0.0029 (5)	0.0027 (5)
C3	0.0393 (10)	0.0376 (11)	0.0273 (8)	−0.0045 (7)	0.0048 (6)	−0.0035 (7)
C4	0.0349 (8)	0.0324 (10)	0.0220 (7)	0.0053 (6)	0.0079 (6)	0.0026 (6)
C5	0.0288 (8)	0.0332 (10)	0.0300 (7)	0.0040 (6)	0.0086 (6)	0.0045 (6)
C6	0.0358 (10)	0.0555 (13)	0.0404 (9)	−0.0026 (8)	0.0161 (7)	0.0056 (9)
C7	0.0261 (8)	0.0366 (10)	0.0313 (7)	−0.0025 (7)	0.0040 (6)	−0.0017 (6)
C8	0.0288 (8)	0.0321 (9)	0.0242 (7)	0.0045 (6)	0.0038 (5)	0.0005 (6)
C9	0.0358 (9)	0.0553 (13)	0.0277 (8)	−0.0060 (8)	0.0079 (6)	−0.0096 (7)
O1	0.0299 (6)	0.0308 (7)	0.0314 (5)	−0.0027 (5)	0.0113 (4)	−0.0019 (4)

Geometric parameters (Å, º)

C1—O1	1.3863 (16)	C5—C6	1.505 (2)
C1—C8	1.391 (2)	C6—H6A	0.98 (3)
C1—C2	1.3953 (19)	C6—H6B	0.91 (3)
C2—C4	1.387 (2)	C6—H6C	0.94 (3)
C2—C3	1.496 (2)	C7—C8	1.385 (2)
C3—H3A	0.97 (2)	C7—H7	0.947 (16)
C3—H3B	0.96 (2)	C8—C9	1.5063 (19)
C3—H3C	0.97 (2)	C9—H9A	0.97 (2)
C4—C5	1.381 (2)	C9—H9B	0.96 (2)
C4—H4	0.984 (16)	C9—H9C	0.95 (2)
C5—C7	1.391 (2)	O1—H1Y	0.89 (2)
O1—C1—C8	116.45 (11)	C5—C6—H6B	112.3 (16)
O1—C1—C2	121.75 (13)	H6A—C6—H6B	106 (2)
C8—C1—C2	121.77 (12)	C5—C6—H6C	110.7 (15)
C4—C2—C1	117.52 (13)	H6A—C6—H6C	102 (2)
C4—C2—C3	121.03 (12)	H6B—C6—H6C	114 (2)
C1—C2—C3	121.44 (13)	C8—C7—C5	122.15 (15)
C2—C3—H3A	112.2 (11)	C8—C7—H7	120.1 (9)
C2—C3—H3B	108.7 (11)	C5—C7—H7	117.7 (9)
H3A—C3—H3B	110.0 (16)	C7—C8—C1	118.10 (12)
C2—C3—H3C	110.3 (13)	C7—C8—C9	120.99 (14)
H3A—C3—H3C	105.5 (17)	C1—C8—C9	120.90 (13)
H3B—C3—H3C	110.1 (16)	C8—C9—H9A	110.7 (12)
C5—C4—C2	122.83 (12)	C8—C9—H9B	112.4 (12)
C5—C4—H4	119.4 (9)	H9A—C9—H9B	109.3 (18)
C2—C4—H4	117.8 (9)	C8—C9—H9C	111.2 (13)
C4—C5—C7	117.62 (13)	H9A—C9—H9C	109.0 (17)
C4—C5—C6	121.49 (13)	H9B—C9—H9C	103.9 (17)
C7—C5—C6	120.86 (15)	C1—O1—H1Y	112.8 (12)
C5—C6—H6A	112.0 (19)
O1—C1—C2—C4	−177.80 (12)	C4—C5—C7—C8	0.2 (2)
C8—C1—C2—C4	0.2 (2)	C6—C5—C7—C8	−178.17 (15)
O1—C1—C2—C3	1.3 (2)	C5—C7—C8—C1	0.3 (2)
C8—C1—C2—C3	179.28 (15)	C5—C7—C8—C9	179.91 (15)
C1—C2—C4—C5	0.4 (2)	O1—C1—C8—C7	177.58 (13)
C3—C2—C4—C5	−178.74 (15)	C2—C1—C8—C7	−0.5 (2)
C2—C4—C5—C7	−0.6 (2)	O1—C1—C8—C9	−2.0 (2)
C2—C4—C5—C6	177.81 (15)	C2—C1—C8—C9	179.89 (14)