5,5-Bis(hydroxy-meth-yl)-3-methyl-cyclo-hex-2-enone.

In the title compound, C(9)H(14)O(3), the cyclo-hexenone ring has an envelope conformation; the flap atom (with the hydroxy-methyl groups attached) is displaced by 0.582 (4) Å from the plane of the other five ring atoms. The crystal structure contains an inter-molecular O-H⋯O hydrogen-bonded ring.

Related literature

For related literature, see: Aghil et al. (1992 ▶); Hu et al. (2003 ▶); Li & Strobel (2001 ▶); Luu et al. (2004 ▶).

Experimental

Crystal data

C9H14O3

M = 170.21

Triclinic,

a = 5.9791 (3) Å

b = 6.2251 (1) Å

c = 13.7493 (8) Å

α = 90.8104 (17)°

β = 91.3285 (12)°

γ = 117.0728 (15)°

V = 455.38 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (1) K

0.43 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.958, T max = 0.982

4514 measured reflections

2060 independent reflections

1432 reflections with F 2 > 2σ(F 2)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.195

S = 1.01

2060 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶) and Larson (1970 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025063/ez2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025063/ez2128Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H14O3	Z = 2
Mr = 170.21	F000 = 184.00
Triclinic, P1	Dx = 1.241 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71075 Å
a = 5.9791 (3) Å	Cell parameters from 3491 reflections
b = 6.22510 (10) Å	θ = 3.7–27.4º
c = 13.7493 (8) Å	µ = 0.09 mm−1
α = 90.8104 (17)º	T = 296 (1) K
β = 91.3285 (12)º	Chunk, colorless
γ = 117.0728 (15)º	0.43 × 0.40 × 0.20 mm
V = 455.38 (4) Å3

Rigaku R-AXIS RAPID diffractometer	1432 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.018
ω scans	θmax = 27.5º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −7→7
Tmin = 0.958, Tmax = 0.982	k = −8→8
4514 measured reflections	l = −17→17
2060 independent reflections

Refinement on F2	w = 1/[0.0027Fo2 + 5σ(Fo2) + 1]/(4Fo2)
R[F2 > 2σ(F2)] = 0.054	(Δ/σ)max < 0.001
wR(F2) = 0.195	Δρmax = 0.29 e Å−3
S = 1.01	Δρmin = −0.23 e Å−3
2060 reflections	Extinction correction: Larson (1970)
110 parameters	Extinction coefficient: 107 (30)
H-atom parameters constrained

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O1	1.1756 (3)	1.1069 (3)	0.16817 (14)	0.0617 (6)
O2	0.8610 (2)	0.5583 (3)	0.38179 (12)	0.0518 (5)
O3	0.3183 (3)	0.5928 (4)	0.43726 (12)	0.0625 (6)
C1	0.6300 (3)	0.7646 (4)	0.31049 (14)	0.0342 (5)
C2	0.4284 (4)	0.7285 (4)	0.23242 (14)	0.0382 (6)
C3	0.5141 (4)	0.7644 (4)	0.13114 (16)	0.0395 (6)
C4	0.7599 (4)	0.8911 (4)	0.11129 (17)	0.0459 (6)
C5	0.9546 (4)	1.0036 (4)	0.18614 (18)	0.0418 (6)
C6	0.8686 (4)	0.9901 (4)	0.29092 (17)	0.0435 (6)
C7	0.3125 (5)	0.6558 (5)	0.05324 (18)	0.0575 (8)
C8	0.6772 (4)	0.5422 (4)	0.31014 (16)	0.0391 (6)
C9	0.5370 (4)	0.7935 (5)	0.41112 (17)	0.0497 (7)
H4	0.8057	0.9066	0.0466	0.055*
H21	0.2949	0.5649	0.2365	0.046*
H22	0.3628	0.8418	0.2467	0.046*
H61	1.0013	0.9953	0.3343	0.052*
H62	0.8404	1.1291	0.3044	0.052*
H71	0.3875	0.6827	−0.0093	0.069*
H72	0.2024	0.7294	0.0564	0.069*
H73	0.2183	0.4855	0.0626	0.069*
H81	0.5204	0.4012	0.3225	0.047*
H82	0.7344	0.5243	0.2465	0.047*
H91	0.6684	0.8209	0.4596	0.060*
H92	0.5042	0.9324	0.4103	0.060*
H201	0.7736	0.4867	0.4357	0.067*
H301	0.1888	0.6149	0.4049	0.081*

	U11	U22	U33	U12	U13	U23
O1	0.0437 (10)	0.0582 (12)	0.0750 (14)	0.0149 (8)	0.0195 (9)	0.0154 (10)
O2	0.0403 (9)	0.0843 (13)	0.0433 (9)	0.0383 (9)	0.0072 (7)	0.0232 (8)
O3	0.0444 (9)	0.1166 (18)	0.0398 (9)	0.0471 (11)	0.0123 (7)	0.0284 (10)
C1	0.0325 (10)	0.0441 (13)	0.0296 (10)	0.0205 (9)	0.0006 (8)	−0.0006 (8)
C2	0.0357 (10)	0.0514 (14)	0.0324 (11)	0.0239 (10)	0.0002 (8)	0.0044 (9)
C3	0.0480 (12)	0.0438 (13)	0.0328 (11)	0.0263 (11)	−0.0014 (9)	0.0041 (9)
C4	0.0556 (14)	0.0524 (15)	0.0333 (11)	0.0272 (12)	0.0097 (10)	0.0090 (10)
C5	0.0422 (12)	0.0347 (12)	0.0508 (13)	0.0190 (10)	0.0108 (10)	0.0086 (10)
C6	0.0423 (12)	0.0411 (13)	0.0437 (13)	0.0163 (10)	−0.0014 (10)	−0.0049 (10)
C7	0.0663 (17)	0.0717 (19)	0.0387 (13)	0.0360 (15)	−0.0145 (12)	−0.0003 (12)
C8	0.0371 (11)	0.0488 (14)	0.0366 (11)	0.0238 (10)	−0.0010 (9)	0.0071 (9)
C9	0.0473 (13)	0.0781 (19)	0.0333 (12)	0.0367 (13)	0.0062 (10)	0.0024 (12)

O1—C5	1.211 (2)	O3—H301	0.948
O2—C8	1.426 (3)	C2—H21	0.970
O3—C9	1.395 (2)	C2—H22	0.970
C1—C2	1.530 (3)	C4—H4	0.930
C1—C6	1.512 (2)	C6—H61	0.970
C1—C8	1.534 (4)	C6—H62	0.970
C1—C9	1.541 (3)	C7—H71	0.960
C2—C3	1.480 (3)	C7—H72	0.960
C3—C4	1.351 (3)	C7—H73	0.960
C3—C7	1.495 (3)	C8—H81	0.970
C4—C5	1.445 (3)	C8—H82	0.970
C5—C6	1.531 (3)	C9—H91	0.970
O2—H201	0.915	C9—H92	0.970
C2—C1—C6	109.76 (18)	C3—C4—H4	118.6
C2—C1—C8	109.12 (18)	C5—C4—H4	118.6
C2—C1—C9	109.4 (2)	C1—C6—H61	108.4
C6—C1—C8	110.8 (2)	C1—C6—H62	108.4
C6—C1—C9	108.79 (18)	C5—C6—H61	108.4
C8—C1—C9	109.0 (2)	C5—C6—H62	108.4
C1—C2—C3	115.5 (2)	H61—C6—H62	109.5
C2—C3—C4	121.45 (19)	C3—C7—H71	109.5
C2—C3—C7	115.92 (19)	C3—C7—H72	109.5
C4—C3—C7	122.6 (2)	C3—C7—H73	109.5
C3—C4—C5	122.9 (2)	H71—C7—H72	109.5
O1—C5—C4	122.5 (2)	H71—C7—H73	109.5
O1—C5—C6	120.8 (2)	H72—C7—H73	109.5
C4—C5—C6	116.7 (2)	O2—C8—H81	108.6
C1—C6—C5	113.84 (17)	O2—C8—H82	108.6
O2—C8—C1	113.12 (18)	C1—C8—H81	108.6
O3—C9—C1	113.6 (2)	C1—C8—H82	108.6
C8—O2—H201	105.8	H81—C8—H82	109.5
C9—O3—H301	103.4	O3—C9—H91	108.4
C1—C2—H21	107.9	O3—C9—H92	108.4
C1—C2—H22	107.9	C1—C9—H91	108.4
C3—C2—H21	107.9	C1—C9—H92	108.4
C3—C2—H22	107.9	H91—C9—H92	109.5
H21—C2—H22	109.5
C2—C1—C6—C5	−50.0 (3)	C8—C1—C9—O3	−58.2 (2)
C6—C1—C2—C3	44.7 (3)	C9—C1—C8—O2	−59.9 (2)
C2—C1—C8—O2	−179.24 (16)	C1—C2—C3—C4	−19.9 (4)
C8—C1—C2—C3	−76.9 (2)	C1—C2—C3—C7	161.0 (2)
C2—C1—C9—O3	61.0 (3)	C2—C3—C4—C5	−1.2 (4)
C9—C1—C2—C3	164.0 (2)	C7—C3—C4—C5	177.8 (3)
C6—C1—C8—O2	59.8 (2)	C3—C4—C5—O1	176.3 (3)
C8—C1—C6—C5	70.6 (2)	C3—C4—C5—C6	−4.6 (4)
C6—C1—C9—O3	−179.1 (2)	O1—C5—C6—C1	−149.4 (2)
C9—C1—C6—C5	−169.7 (2)	C4—C5—C6—C1	31.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H201···O3i	0.92	1.85	2.738 (2)	163
O3—H301···O2ii	0.95	1.85	2.733 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H201⋯O3i	0.92	1.85	2.738 (2)	163
O3—H301⋯O2ii	0.95	1.84	2.733 (2)	155

Symmetry codes: (i) ; (ii) .