1-(2,6-Di­hydroxy­phenyl)­ethano­ne

The title compound, C₈H₈O₃, has several intra- and intermolecular hydrogen bonds in its crystal structure. There are two molecules in the asymmetric unit, and they are extended into infinite chains along [011] by intermolecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.122
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   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

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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-(2,6-Dihydroxyphenyl)ethanone

Crystal data

C8H8O3	Z = 4
Mr = 152.14	F(000) = 320
Triclinic, P1	Dx = 1.400 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.646 (3) Å	Cell parameters from 816 reflections
b = 8.325 (3) Å	θ = 2.8–26.0°
c = 12.803 (5) Å	µ = 0.11 mm^−1
α = 73.321 (6)°	T = 293 K
β = 79.042 (7)°	Block, colorless
γ = 68.230 (6)°	0.48 × 0.42 × 0.35 mm
V = 721.8 (5) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3115 independent reflections
Radiation source: fine-focus sealed tube	2065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.950, Tmax = 0.963	k = −10→10
6117 measured reflections	l = −15→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 0.1147P] where P = (Fo^2 + 2Fc^2)/3
3115 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

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.

The reflections (112), (201) and (221) were omitted during the refinement as they fitted very badly.

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

	x	y	z	Uiso*/Ueq
C1	0.26635 (19)	0.95765 (18)	0.53861 (12)	0.0380 (3)
C2	0.2177 (2)	1.12158 (19)	0.45953 (12)	0.0426 (4)
C3	0.2032 (2)	1.2773 (2)	0.48432 (14)	0.0502 (4)
H3A	0.1722	1.3840	0.4313	0.060*
C4	0.2341 (3)	1.2751 (2)	0.58669 (15)	0.0557 (4)
H4B	0.2245	1.3808	0.6022	0.067*
C5	0.2792 (2)	1.1193 (2)	0.66725 (14)	0.0538 (4)
H5B	0.2986	1.1197	0.7367	0.065*
C6	0.2951 (2)	0.9628 (2)	0.64337 (12)	0.0435 (4)
C7	0.2874 (2)	0.7856 (2)	0.51869 (13)	0.0459 (4)
C8	0.2737 (3)	0.7627 (2)	0.40968 (15)	0.0588 (5)
H8A	0.3109	0.6381	0.4124	0.088*
H8B	0.3558	0.8139	0.3554	0.088*
H8C	0.1457	0.8212	0.3910	0.088*
C9	0.9792 (2)	0.67317 (19)	0.06530 (12)	0.0412 (4)
C10	0.7867 (2)	0.6848 (2)	0.07773 (13)	0.0480 (4)
C11	0.6690 (3)	0.7894 (3)	−0.00340 (15)	0.0634 (5)
H11A	0.5429	0.7965	0.0061	0.076*
C12	0.7383 (3)	0.8824 (3)	−0.09775 (15)	0.0714 (6)
H12A	0.6579	0.9531	−0.1520	0.086*
C13	0.9239 (3)	0.8737 (3)	−0.11432 (14)	0.0619 (5)
H13A	0.9682	0.9380	−0.1793	0.074*
C14	1.0449 (2)	0.7696 (2)	−0.03458 (12)	0.0461 (4)
C15	1.0988 (2)	0.5602 (2)	0.15321 (13)	0.0493 (4)
C16	1.2942 (3)	0.5566 (3)	0.15443 (17)	0.0807 (7)
H16A	1.3413	0.4849	0.2232	0.121*
H16B	1.2931	0.6757	0.1448	0.121*
H16C	1.3745	0.5070	0.0960	0.121*
O1	0.18399 (18)	1.12321 (15)	0.35927 (9)	0.0613 (4)
H1A	0.1402	1.2265	0.3246	0.092*
O2	0.34158 (17)	0.81284 (15)	0.72461 (9)	0.0577 (3)
H2A	0.3452	0.7281	0.7027	0.087*
O3	0.3195 (2)	0.65157 (15)	0.59555 (10)	0.0668 (4)
O4	0.70932 (17)	0.59749 (18)	0.16908 (10)	0.0655 (4)
H4A	0.7912	0.5354	0.2108	0.098*
O5	1.22919 (17)	0.75656 (18)	−0.05141 (9)	0.0633 (4)
H5A	1.2627	0.7726	−0.1172	0.095*
O6	1.03520 (18)	0.46479 (17)	0.23303 (10)	0.0654 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0355 (8)	0.0339 (8)	0.0401 (8)	−0.0129 (6)	−0.0008 (6)	−0.0022 (6)
C2	0.0438 (9)	0.0377 (8)	0.0410 (9)	−0.0149 (7)	−0.0041 (7)	0.0003 (7)
C3	0.0560 (10)	0.0335 (8)	0.0536 (10)	−0.0147 (7)	−0.0060 (8)	0.0009 (7)
C4	0.0647 (11)	0.0404 (9)	0.0650 (12)	−0.0207 (8)	−0.0032 (9)	−0.0147 (8)
C5	0.0610 (11)	0.0554 (10)	0.0476 (10)	−0.0212 (9)	−0.0060 (8)	−0.0132 (8)
C6	0.0413 (9)	0.0413 (8)	0.0393 (8)	−0.0134 (7)	−0.0012 (6)	0.0009 (7)
C7	0.0440 (9)	0.0379 (8)	0.0509 (9)	−0.0159 (7)	−0.0009 (7)	−0.0027 (7)
C8	0.0702 (12)	0.0487 (10)	0.0627 (11)	−0.0253 (9)	−0.0056 (9)	−0.0143 (8)
C9	0.0475 (9)	0.0350 (8)	0.0398 (8)	−0.0119 (7)	−0.0066 (7)	−0.0079 (6)
C10	0.0503 (10)	0.0479 (9)	0.0447 (9)	−0.0157 (8)	−0.0024 (7)	−0.0115 (7)
C11	0.0459 (10)	0.0805 (14)	0.0563 (11)	−0.0136 (9)	−0.0082 (8)	−0.0132 (10)
C12	0.0590 (12)	0.0870 (15)	0.0471 (10)	−0.0064 (10)	−0.0157 (9)	−0.0017 (10)
C13	0.0599 (11)	0.0681 (12)	0.0405 (9)	−0.0146 (9)	−0.0053 (8)	0.0038 (8)
C14	0.0501 (9)	0.0459 (9)	0.0391 (9)	−0.0139 (7)	−0.0049 (7)	−0.0077 (7)
C15	0.0542 (10)	0.0428 (9)	0.0428 (9)	−0.0115 (7)	−0.0057 (7)	−0.0036 (7)
C16	0.0612 (13)	0.1072 (18)	0.0586 (12)	−0.0314 (12)	−0.0226 (10)	0.0179 (11)
O1	0.0869 (9)	0.0450 (7)	0.0460 (7)	−0.0201 (6)	−0.0212 (6)	0.0048 (5)
O2	0.0731 (8)	0.0477 (7)	0.0414 (7)	−0.0186 (6)	−0.0073 (6)	0.0048 (5)
O3	0.0957 (10)	0.0363 (6)	0.0616 (8)	−0.0246 (6)	−0.0093 (7)	0.0031 (6)
O4	0.0587 (8)	0.0746 (9)	0.0605 (8)	−0.0328 (7)	−0.0028 (6)	0.0000 (7)
O5	0.0559 (8)	0.0864 (9)	0.0432 (7)	−0.0318 (7)	−0.0035 (5)	0.0008 (6)
O6	0.0651 (8)	0.0574 (7)	0.0551 (7)	−0.0180 (6)	−0.0095 (6)	0.0136 (6)

Geometric parameters (Å, º)

C1—C2	1.414 (2)	C9—C15	1.461 (2)
C1—C6	1.415 (2)	C10—O4	1.3469 (19)
C1—C7	1.472 (2)	C10—C11	1.379 (2)
C2—O1	1.3519 (19)	C11—C12	1.365 (3)
C2—C3	1.382 (2)	C11—H11A	0.9300
C3—C4	1.369 (2)	C12—C13	1.372 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.379 (2)	C13—C14	1.381 (2)
C4—H4B	0.9300	C13—H13A	0.9300
C5—C6	1.379 (2)	C14—O5	1.352 (2)
C5—H5B	0.9300	C15—O6	1.2425 (19)
C6—O2	1.3539 (18)	C15—C16	1.486 (3)
C7—O3	1.2378 (19)	C16—H16A	0.9600
C7—C8	1.489 (2)	C16—H16B	0.9600
C8—H8A	0.9600	C16—H16C	0.9600
C8—H8B	0.9600	O1—H1A	0.8200
C8—H8C	0.9600	O2—H2A	0.8200
C9—C14	1.413 (2)	O4—H4A	0.8200
C9—C10	1.420 (2)	O5—H5A	0.8200
C2—C1—C6	116.73 (14)	C10—C9—C15	119.18 (14)
C2—C1—C7	124.35 (14)	O4—C10—C11	116.81 (16)
C6—C1—C7	118.93 (13)	O4—C10—C9	122.10 (15)
O1—C2—C3	120.58 (13)	C11—C10—C9	121.08 (16)
O1—C2—C1	118.60 (14)	C12—C11—C10	119.73 (18)
C3—C2—C1	120.81 (15)	C12—C11—H11A	120.1
C4—C3—C2	120.25 (15)	C10—C11—H11A	120.1
C4—C3—H3A	119.9	C11—C12—C13	121.42 (17)
C2—C3—H3A	119.9	C11—C12—H12A	119.3
C3—C4—C5	121.25 (16)	C13—C12—H12A	119.3
C3—C4—H4B	119.4	C12—C13—C14	120.02 (17)
C5—C4—H4B	119.4	C12—C13—H13A	120.0
C6—C5—C4	119.06 (16)	C14—C13—H13A	120.0
C6—C5—H5B	120.5	O5—C14—C13	120.41 (15)
C4—C5—H5B	120.5	O5—C14—C9	118.87 (14)
O2—C6—C5	117.02 (15)	C13—C14—C9	120.72 (16)
O2—C6—C1	121.09 (14)	O6—C15—C9	119.49 (16)
C5—C6—C1	121.89 (14)	O6—C15—C16	117.25 (15)
O3—C7—C1	119.07 (15)	C9—C15—C16	123.23 (15)
O3—C7—C8	117.52 (15)	C15—C16—H16A	109.5
C1—C7—C8	123.41 (14)	C15—C16—H16B	109.5
C7—C8—H8A	109.5	H16A—C16—H16B	109.5
C7—C8—H8B	109.5	C15—C16—H16C	109.5
H8A—C8—H8B	109.5	H16A—C16—H16C	109.5
C7—C8—H8C	109.5	H16B—C16—H16C	109.5
H8A—C8—H8C	109.5	C2—O1—H1A	109.5
H8B—C8—H8C	109.5	C6—O2—H2A	109.5
C14—C9—C10	117.00 (14)	C10—O4—H4A	109.5
C14—C9—C15	123.79 (15)	C14—O5—H5A	109.5
C6—C1—C2—O1	−178.24 (13)	C14—C9—C10—O4	179.49 (14)
C7—C1—C2—O1	1.5 (2)	C15—C9—C10—O4	1.3 (2)
C6—C1—C2—C3	1.2 (2)	C14—C9—C10—C11	−1.6 (2)
C7—C1—C2—C3	−179.14 (14)	C15—C9—C10—C11	−179.77 (16)
O1—C2—C3—C4	178.78 (15)	O4—C10—C11—C12	179.54 (17)
C1—C2—C3—C4	−0.6 (2)	C9—C10—C11—C12	0.5 (3)
C2—C3—C4—C5	−0.4 (3)	C10—C11—C12—C13	0.3 (3)
C3—C4—C5—C6	0.7 (3)	C11—C12—C13—C14	−0.1 (3)
C4—C5—C6—O2	179.32 (15)	C12—C13—C14—O5	178.25 (17)
C4—C5—C6—C1	−0.1 (2)	C12—C13—C14—C9	−1.0 (3)
C2—C1—C6—O2	179.81 (13)	C10—C9—C14—O5	−177.47 (14)
C7—C1—C6—O2	0.1 (2)	C15—C9—C14—O5	0.7 (2)
C2—C1—C6—C5	−0.8 (2)	C10—C9—C14—C13	1.8 (2)
C7—C1—C6—C5	179.46 (15)	C15—C9—C14—C13	179.89 (16)
C2—C1—C7—O3	−175.79 (15)	C14—C9—C15—O6	−172.02 (15)
C6—C1—C7—O3	3.9 (2)	C10—C9—C15—O6	6.1 (2)
C2—C1—C7—C8	4.7 (2)	C14—C9—C15—C16	9.9 (3)
C6—C1—C7—C8	−175.56 (14)	C10—C9—C15—C16	−172.01 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6^i	0.82	1.95	2.767 (2)	176
O2—H2A···O3	0.82	1.74	2.472 (2)	148
O4—H4A···O6	0.82	1.79	2.513 (2)	146
O5—H5A···O2^ii	0.82	1.97	2.7878 (19)	180

Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y, z−1.