1-(2,4-Di­hydroxy-3,5-di­methylphenyl)-ethano­ne (Clavatol)

The structure of the title mol­ecule, C₁₀H₁₂O₃, is stabilized by an intramolecular O—H...O hydrogen bond. In the crystal structure, the glide-related mol­ecules are linked by O—H...O hydrogen bonds to form molecular chains along [201]. The structure is further stabilized by π...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.155
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.57
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C10

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1-(2,4-Dihydroxy-3,5-dimethyl-phenyl)-ethanone

Crystal data

C10H12O3	F(000) = 384
Mr = 180.20	Dx = 1.324 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3017 reflections
a = 8.318 (1) Å	θ = 2.4–28.0°
b = 15.200 (3) Å	µ = 0.10 mm^−1
c = 7.204 (1) Å	T = 298 K
β = 96.896 (3)°	Block, colorless
V = 904.2 (2) Å^3	0.35 × 0.23 × 0.18 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2078 independent reflections
Radiation source: fine-focus sealed tube	1725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scan	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.947, Tmax = 0.983	k = −17→20
5370 measured reflections	l = −8→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0945P)^2 + 0.142P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2078 reflections	Δρmax = 0.22 e Å^−3
125 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (8)

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

	x	y	z	Uiso*/Ueq
O1	0.69574 (13)	0.24726 (7)	0.17498 (18)	0.0609 (4)
O2	0.51388 (12)	0.37873 (7)	0.08559 (18)	0.0591 (4)
O3	−0.01831 (11)	0.32842 (7)	−0.17279 (16)	0.0559 (3)
C1	0.42724 (15)	0.22866 (9)	0.04071 (18)	0.0397 (3)
C2	0.39759 (14)	0.31959 (9)	0.02716 (18)	0.0406 (3)
C3	0.24782 (15)	0.35241 (9)	−0.04823 (18)	0.0418 (3)
C4	0.12568 (14)	0.29264 (10)	−0.10492 (18)	0.0396 (3)
C5	0.14846 (15)	0.20111 (9)	−0.09173 (17)	0.0403 (3)
C6	0.29907 (15)	0.17190 (9)	−0.02101 (18)	0.0418 (3)
C7	0.58499 (15)	0.19577 (10)	0.11649 (19)	0.0460 (4)
C8	0.61857 (19)	0.09957 (12)	0.1245 (3)	0.0632 (5)
C9	0.2196 (2)	0.44927 (11)	−0.0692 (3)	0.0629 (5)
C10	0.01309 (18)	0.13858 (11)	−0.1530 (2)	0.0538 (4)
H2	0.5968	0.3527	0.1273	0.089*
H3	−0.0826	0.2891	−0.2071	0.084*
H6	0.3172	0.1116	−0.0136	0.063*
H8A	0.7302	0.0899	0.1713	0.095*
H8B	0.5966	0.0749	0.0014	0.095*
H8C	0.5506	0.0719	0.2061	0.095*
H9A	0.1592	0.4611	−0.1887	0.094*
H9B	0.3219	0.4792	−0.0608	0.094*
H9C	0.1598	0.4697	0.0282	0.094*
H10A	0.0507	0.0792	−0.1338	0.081*
H10B	−0.0231	0.1476	−0.2832	0.081*
H10C	−0.0751	0.1489	−0.0811	0.081*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0290 (5)	0.0665 (7)	0.0808 (8)	−0.0049 (4)	−0.0191 (5)	0.0076 (6)
O2	0.0332 (6)	0.0524 (6)	0.0862 (8)	−0.0120 (4)	−0.0159 (5)	0.0016 (5)
O3	0.0268 (5)	0.0630 (7)	0.0733 (7)	0.0035 (4)	−0.0130 (4)	−0.0029 (5)
C1	0.0264 (6)	0.0510 (7)	0.0395 (7)	−0.0041 (5)	−0.0053 (5)	0.0043 (5)
C2	0.0268 (6)	0.0499 (8)	0.0432 (7)	−0.0080 (5)	−0.0042 (5)	0.0007 (5)
C3	0.0295 (6)	0.0479 (7)	0.0464 (7)	−0.0021 (5)	−0.0022 (5)	−0.0009 (5)
C4	0.0240 (6)	0.0546 (8)	0.0384 (6)	−0.0009 (5)	−0.0032 (4)	−0.0015 (5)
C5	0.0281 (6)	0.0528 (8)	0.0383 (6)	−0.0070 (5)	−0.0031 (5)	−0.0013 (5)
C6	0.0314 (6)	0.0470 (7)	0.0447 (7)	−0.0046 (5)	−0.0047 (5)	0.0022 (5)
C7	0.0278 (6)	0.0589 (8)	0.0485 (7)	−0.0029 (6)	−0.0064 (5)	0.0086 (6)
C8	0.0394 (8)	0.0595 (10)	0.0862 (12)	0.0038 (7)	−0.0112 (7)	0.0134 (8)
C9	0.0422 (8)	0.0495 (8)	0.0934 (13)	0.0006 (6)	−0.0067 (8)	−0.0017 (8)
C10	0.0342 (7)	0.0587 (9)	0.0648 (9)	−0.0115 (6)	−0.0087 (6)	−0.0035 (7)

Geometric parameters (Å, º)

O1—C7	1.243 (2)	O2—H2	0.82
O2—C2	1.350 (2)	O3—H3	0.82
O3—C4	1.352 (2)	C6—H6	0.93
C1—C6	1.402 (2)	C8—H8A	0.96
C1—C2	1.405 (2)	C8—H8B	0.96
C1—C7	1.448 (2)	C8—H8C	0.96
C2—C3	1.390 (2)	C9—H9A	0.96
C3—C4	1.387 (2)	C9—H9B	0.96
C3—C9	1.496 (2)	C9—H9C	0.96
C4—C5	1.406 (2)	C10—H10A	0.96
C5—C6	1.369 (2)	C10—H10B	0.96
C5—C10	1.499 (2)	C10—H10C	0.96
C7—C8	1.489 (2)
C2—O2—H2	109.5	C5—C6—H6	118.5
C4—O3—H3	109.5	C1—C6—H6	118.5
C6—C1—C2	117.6 (1)	C7—C8—H8A	109.5
C6—C1—C7	121.8 (1)	C7—C8—H8B	109.5
C2—C1—C7	120.6 (1)	H8A—C8—H8B	109.5
O2—C2—C3	117.2 (1)	C7—C8—H8C	109.5
O2—C2—C1	121.3 (1)	H8A—C8—H8C	109.5
C3—C2—C1	121.4 (1)	H8B—C8—H8C	109.5
C4—C3—C2	118.1 (1)	C3—C9—H9A	109.5
C4—C3—C9	121.0 (1)	C3—C9—H9B	109.5
C2—C3—C9	121.0 (1)	H9A—C9—H9B	109.5
O3—C4—C3	115.4 (1)	C3—C9—H9C	109.5
O3—C4—C5	121.9 (1)	H9A—C9—H9C	109.5
C3—C4—C5	122.7 (1)	H9B—C9—H9C	109.5
C6—C5—C4	117.1 (1)	C5—C10—H10A	109.5
C6—C5—C10	121.7 (1)	C5—C10—H10B	109.5
C4—C5—C10	121.2 (1)	C5—C10—H10C	109.5
C5—C6—C1	123.1 (1)	H10A—C10—H10B	109.5
O1—C7—C1	120.8 (1)	H10A—C10—H10C	109.5
O1—C7—C8	118.5 (1)	H10B—C10—H10C	109.5
C1—C7—C8	120.7 (1)
C6—C1—C2—O2	179.19 (12)	O3—C4—C5—C6	179.99 (12)
C7—C1—C2—O2	−0.6 (2)	C3—C4—C5—C6	−0.6 (2)
C6—C1—C2—C3	−1.3 (2)	O3—C4—C5—C10	0.1 (2)
C7—C1—C2—C3	178.85 (12)	C3—C4—C5—C10	179.48 (13)
O2—C2—C3—C4	−178.50 (12)	C4—C5—C6—C1	1.3 (2)
C1—C2—C3—C4	2.0 (2)	C2—C1—C6—C5	−0.4 (2)
O2—C2—C3—C9	2.1 (2)	C7—C1—C6—C5	179.43 (12)
C1—C2—C3—C9	−177.45 (14)	C6—C1—C7—O1	−178.10 (13)
C2—C3—C4—O3	178.44 (12)	C2—C1—C7—O1	1.7 (2)
C9—C3—C4—O3	−2.1 (2)	C6—C1—C7—C8	2.5 (2)
C2—C3—C4—C5	−1.0 (2)	C2—C1—C7—C8	−177.72 (14)
C9—C3—C4—C5	178.42 (14)	C10—C5—C6—C1	−178.76 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.82	2.542 (2)	147
O3—H3···O1^i	0.82	2.01	2.749 (1)	149

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