1-(2,6-Dihydroxy­phenyl)butanone

The title compound, C₁₀H₁₂O₃, has several intra- and intermolecular hydrogen bonds in the crystal structure. The molecules are linked into infinite chains along [011] via intermolecular O—H...O hydrogen bonds. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.143
• Data-to-parameter ratio = 14.7

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 .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C18'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C19'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C10 H12 O3

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

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

---

Computing details

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

1-(2,6-Dihydroxyphenyl)butanone

Crystal data

C10H12O3	Z = 4
Mr = 180.20	F(000) = 384
Triclinic, P1	Dx = 1.289 Mg m^−3
a = 7.805 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.705 (5) Å	Cell parameters from 897 reflections
c = 11.805 (5) Å	θ = 3.4–26.5°
α = 107.729 (7)°	µ = 0.10 mm^−1
β = 98.068 (7)°	T = 293 K
γ = 91.090 (8)°	Block, colorless
V = 928.2 (7) Å^3	0.40 × 0.38 × 0.35 mm

Data collection

Bruker SMART 1000 CCD diffractometer	3993 independent reflections
Radiation source: fine-focus sealed tube	2322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.963, Tmax = 0.968	k = −13→13
7939 measured reflections	l = −14→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 0.0999P] where P = (Fo^2 + 2Fc^2)/3
3993 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.16 e Å^−3
31 restraints	Δρmin = −0.29 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11	1.0610 (2)	0.87377 (15)	0.56687 (14)	0.0483 (4)
C12	1.2393 (3)	0.87757 (17)	0.55706 (17)	0.0584 (5)
C13	1.3560 (3)	0.9696 (2)	0.6412 (2)	0.0810 (7)
H13	1.4734	0.9697	0.6345	0.097*
C14	1.2983 (3)	1.0606 (2)	0.7344 (2)	0.0854 (7)
H14	1.3776	1.1222	0.7910	0.102*
C15	1.1259 (3)	1.06332 (18)	0.74642 (17)	0.0687 (6)
H15	1.0891	1.1267	0.8100	0.082*
C16	1.0079 (2)	0.97176 (16)	0.66395 (15)	0.0535 (4)
C17	0.9421 (2)	0.77360 (17)	0.47577 (16)	0.0587 (5)
C18	0.7544 (3)	0.7563 (2)	0.4817 (2)	0.0898 (8)	0.437 (5)
H18A	0.6917	0.8106	0.4398	0.108*	0.437 (5)
H18B	0.7382	0.7892	0.5654	0.108*	0.437 (5)
C19	0.6705 (5)	0.6128 (4)	0.4280 (4)	0.0623 (15)	0.437 (5)
H19A	0.5496	0.6178	0.4387	0.075*	0.437 (5)
H19B	0.6721	0.5877	0.3420	0.075*	0.437 (5)
C20	0.734 (2)	0.5013 (14)	0.4674 (12)	0.078 (3)	0.437 (5)
H20A	0.6643	0.4226	0.4212	0.118*	0.437 (5)
H20B	0.7265	0.5187	0.5512	0.118*	0.437 (5)
H20C	0.8526	0.4900	0.4552	0.118*	0.437 (5)
C18'	0.7544 (3)	0.7563 (2)	0.4817 (2)	0.0898 (8)	0.563 (5)
H18C	0.7110	0.8429	0.5099	0.108*	0.563 (5)
H18D	0.6950	0.7147	0.4005	0.108*	0.563 (5)
C19'	0.7100 (5)	0.6882 (4)	0.5493 (4)	0.0700 (12)	0.563 (5)
H19C	0.5886	0.6995	0.5567	0.084*	0.563 (5)
H19D	0.7764	0.7248	0.6291	0.084*	0.563 (5)
C20'	0.736 (2)	0.5418 (10)	0.5052 (11)	0.094 (3)	0.563 (5)
H20D	0.7027	0.5013	0.5619	0.140*	0.563 (5)
H20E	0.8553	0.5287	0.4976	0.140*	0.563 (5)
H20F	0.6650	0.5028	0.4283	0.140*	0.563 (5)
O4	1.3046 (2)	0.79287 (15)	0.46624 (14)	0.0762 (4)
O5	0.83807 (19)	0.97438 (14)	0.67483 (13)	0.0763 (5)
O6	1.00038 (17)	0.69735 (13)	0.38976 (11)	0.0701 (4)
C1	0.7832 (2)	1.40267 (16)	0.98760 (14)	0.0494 (4)
C2	0.7867 (2)	1.26412 (17)	0.94253 (16)	0.0586 (5)
C3	0.8439 (3)	1.1909 (2)	1.0154 (2)	0.0769 (6)
H3	0.8432	1.1000	0.9838	0.092*
C4	0.9023 (3)	1.2521 (2)	1.1349 (2)	0.0809 (6)
H4A	0.9404	1.2020	1.1844	0.097*
C5	0.9054 (3)	1.3864 (2)	1.18280 (18)	0.0690 (6)
H5A	0.9473	1.4268	1.2639	0.083*
C6	0.8464 (2)	1.46099 (17)	1.11071 (15)	0.0535 (4)
C7	0.7150 (2)	1.47458 (18)	0.90486 (16)	0.0564 (5)
C8	0.6939 (2)	1.61940 (18)	0.94548 (16)	0.0593 (5)
H8A	0.8073	1.6646	0.9787	0.071*
H8B	0.6240	1.6391	1.0097	0.071*
C9	0.6113 (3)	1.6734 (2)	0.8485 (2)	0.0796 (6)
H9A	0.4936	1.6350	0.8201	0.096*
H9B	0.6754	1.6485	0.7811	0.096*
C10	0.6080 (4)	1.8214 (2)	0.8929 (3)	0.1071 (9)
H10C	0.7245	1.8600	0.9179	0.161*
H10B	0.5451	1.8466	0.9599	0.161*
H10A	0.5520	1.8517	0.8293	0.161*
O1	0.73062 (19)	1.19970 (14)	0.82407 (13)	0.0752 (4)
O2	0.8497 (2)	1.59283 (12)	1.15701 (12)	0.0715 (4)
O3	0.6720 (2)	1.41443 (14)	0.79657 (12)	0.0871 (5)
H4	1.211 (3)	0.742 (2)	0.421 (2)	0.097 (8)*
H5	0.816 (3)	1.044 (2)	0.728 (2)	0.088 (7)*
H2	0.891 (3)	1.616 (2)	1.236 (2)	0.110 (9)*
H1	0.696 (4)	1.266 (3)	0.788 (3)	0.131 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0611 (11)	0.0384 (9)	0.0429 (9)	0.0059 (7)	0.0048 (8)	0.0101 (7)
C12	0.0655 (12)	0.0489 (10)	0.0566 (11)	0.0073 (9)	0.0081 (9)	0.0106 (8)
C13	0.0638 (13)	0.0724 (14)	0.0887 (16)	−0.0032 (11)	0.0044 (12)	0.0020 (12)
C14	0.0798 (16)	0.0706 (14)	0.0787 (15)	−0.0140 (12)	−0.0059 (12)	−0.0073 (12)
C15	0.0836 (15)	0.0524 (11)	0.0554 (11)	−0.0024 (10)	0.0066 (10)	−0.0027 (9)
C16	0.0669 (12)	0.0415 (9)	0.0488 (10)	0.0053 (8)	0.0067 (9)	0.0097 (8)
C17	0.0665 (12)	0.0443 (9)	0.0551 (11)	0.0095 (8)	0.0046 (9)	0.0021 (8)
C18	0.0642 (14)	0.0667 (14)	0.1027 (18)	0.0011 (11)	0.0069 (12)	−0.0234 (13)
C19	0.053 (2)	0.060 (3)	0.060 (3)	0.0022 (19)	0.003 (2)	0.001 (2)
C20	0.079 (5)	0.076 (7)	0.077 (6)	0.001 (5)	0.014 (4)	0.019 (4)
C18'	0.0642 (14)	0.0667 (14)	0.1027 (18)	0.0011 (11)	0.0069 (12)	−0.0234 (13)
C19'	0.069 (2)	0.064 (2)	0.074 (3)	0.0088 (18)	0.0110 (19)	0.0159 (19)
C20'	0.093 (4)	0.082 (6)	0.110 (8)	0.013 (5)	0.028 (5)	0.030 (4)
O4	0.0687 (10)	0.0694 (9)	0.0789 (10)	0.0094 (8)	0.0189 (8)	0.0023 (8)
O5	0.0751 (10)	0.0578 (8)	0.0745 (10)	0.0024 (7)	0.0201 (7)	−0.0147 (7)
O6	0.0742 (9)	0.0617 (8)	0.0548 (8)	0.0090 (7)	0.0043 (6)	−0.0085 (6)
C1	0.0521 (10)	0.0462 (9)	0.0437 (9)	−0.0020 (7)	0.0127 (8)	0.0026 (7)
C2	0.0615 (11)	0.0495 (10)	0.0548 (11)	−0.0040 (8)	0.0141 (9)	−0.0005 (9)
C3	0.0987 (17)	0.0465 (11)	0.0811 (16)	0.0014 (11)	0.0186 (13)	0.0116 (11)
C4	0.1067 (18)	0.0658 (14)	0.0756 (15)	0.0104 (12)	0.0171 (13)	0.0283 (12)
C5	0.0889 (15)	0.0671 (13)	0.0477 (11)	0.0057 (11)	0.0128 (10)	0.0118 (10)
C6	0.0610 (11)	0.0485 (10)	0.0453 (10)	−0.0004 (8)	0.0141 (8)	0.0037 (8)
C7	0.0552 (11)	0.0580 (11)	0.0455 (10)	−0.0021 (8)	0.0067 (8)	0.0013 (8)
C8	0.0624 (12)	0.0580 (11)	0.0533 (11)	0.0036 (9)	0.0103 (9)	0.0106 (8)
C9	0.0828 (15)	0.0808 (15)	0.0752 (14)	0.0093 (12)	0.0048 (11)	0.0271 (12)
C10	0.129 (2)	0.0833 (17)	0.119 (2)	0.0266 (16)	0.0144 (18)	0.0466 (16)
O1	0.0876 (10)	0.0541 (8)	0.0611 (9)	−0.0022 (7)	0.0058 (7)	−0.0129 (7)
O2	0.1044 (11)	0.0519 (8)	0.0441 (8)	0.0041 (7)	0.0029 (7)	−0.0021 (6)
O3	0.1186 (13)	0.0731 (10)	0.0491 (8)	0.0090 (8)	−0.0089 (8)	−0.0016 (7)

Geometric parameters (Å, º)

C11—C12	1.414 (3)	C20'—H20F	0.9600
C11—C16	1.415 (2)	O4—H4	0.90 (2)
C11—C17	1.465 (2)	O5—H5	0.85 (2)
C12—O4	1.345 (2)	C1—C6	1.407 (2)
C12—C13	1.380 (3)	C1—C2	1.417 (2)
C13—C14	1.366 (3)	C1—C7	1.469 (3)
C13—H13	0.9300	C2—O1	1.361 (2)
C14—C15	1.372 (3)	C2—C3	1.367 (3)
C14—H14	0.9300	C3—C4	1.369 (3)
C15—C16	1.374 (2)	C3—H3	0.9300
C15—H15	0.9300	C4—C5	1.374 (3)
C16—O5	1.350 (2)	C4—H4A	0.9300
C17—O6	1.242 (2)	C5—C6	1.375 (3)
C17—C18	1.487 (3)	C5—H5A	0.9300
C18—C19	1.562 (5)	C6—O2	1.348 (2)
C18—H18A	0.9700	C7—O3	1.238 (2)
C18—H18B	0.9700	C7—C8	1.496 (3)
C19—C20	1.478 (19)	C8—C9	1.507 (3)
C19—H19A	0.9700	C8—H8A	0.9700
C19—H19B	0.9700	C8—H8B	0.9700
C20—H20A	0.9600	C9—C10	1.512 (3)
C20—H20B	0.9600	C9—H9A	0.9700
C20—H20C	0.9600	C9—H9B	0.9700
C19'—C20'	1.521 (11)	C10—H10C	0.9600
C19'—H19C	0.9700	C10—H10B	0.9600
C19'—H19D	0.9700	C10—H10A	0.9600
C20'—H20D	0.9600	O1—H1	0.96 (3)
C20'—H20E	0.9600	O2—H2	0.90 (3)
C12—C11—C16	116.77 (16)	H20D—C20'—H20F	109.5
C12—C11—C17	119.21 (15)	H20E—C20'—H20F	109.5
C16—C11—C17	123.98 (17)	C12—O4—H4	103.7 (15)
O4—C12—C13	116.42 (19)	C16—O5—H5	112.1 (15)
O4—C12—C11	122.40 (16)	C6—C1—C2	116.28 (17)
C13—C12—C11	121.18 (18)	C6—C1—C7	124.86 (16)
C14—C13—C12	119.6 (2)	C2—C1—C7	118.86 (16)
C14—C13—H13	120.2	O1—C2—C3	117.91 (18)
C12—C13—H13	120.2	O1—C2—C1	120.26 (18)
C13—C14—C15	121.55 (19)	C3—C2—C1	121.82 (17)
C13—C14—H14	119.2	C2—C3—C4	119.71 (19)
C15—C14—H14	119.2	C2—C3—H3	120.1
C14—C15—C16	119.64 (19)	C4—C3—H3	120.1
C14—C15—H15	120.2	C3—C4—C5	120.9 (2)
C16—C15—H15	120.2	C3—C4—H4A	119.6
O5—C16—C15	119.94 (17)	C5—C4—H4A	119.6
O5—C16—C11	118.85 (15)	C4—C5—C6	119.93 (19)
C15—C16—C11	121.21 (19)	C4—C5—H5A	120.0
O6—C17—C11	118.82 (18)	C6—C5—H5A	120.0
O6—C17—C18	117.78 (16)	O2—C6—C5	120.23 (17)
C11—C17—C18	123.39 (16)	O2—C6—C1	118.43 (17)
C17—C18—C19	116.2 (2)	C5—C6—C1	121.33 (17)
C17—C18—H18A	108.2	O3—C7—C1	119.55 (16)
C19—C18—H18A	108.2	O3—C7—C8	117.59 (18)
C17—C18—H18B	108.2	C1—C7—C8	122.86 (15)
C19—C18—H18B	108.2	C7—C8—C9	114.83 (17)
H18A—C18—H18B	107.4	C7—C8—H8A	108.6
C20—C19—C18	123.9 (6)	C9—C8—H8A	108.6
C20—C19—H19A	106.3	C7—C8—H8B	108.6
C18—C19—H19A	106.3	C9—C8—H8B	108.6
C20—C19—H19B	106.3	H8A—C8—H8B	107.5
C18—C19—H19B	106.3	C8—C9—C10	112.0 (2)
H19A—C19—H19B	106.4	C8—C9—H9A	109.2
C19—C20—H20A	109.5	C10—C9—H9A	109.2
C19—C20—H20B	109.5	C8—C9—H9B	109.2
H20A—C20—H20B	109.5	C10—C9—H9B	109.2
C19—C20—H20C	109.5	H9A—C9—H9B	107.9
H20A—C20—H20C	109.5	C9—C10—H10C	109.5
H20B—C20—H20C	109.5	C9—C10—H10B	109.5
C20'—C19'—H19C	108.3	H10C—C10—H10B	109.5
C20'—C19'—H19D	108.3	C9—C10—H10A	109.5
H19C—C19'—H19D	107.4	H10C—C10—H10A	109.5
C19'—C20'—H20D	109.5	H10B—C10—H10A	109.5
C19'—C20'—H20E	109.5	C2—O1—H1	106.2 (18)
H20D—C20'—H20E	109.5	C6—O2—H2	108.7 (16)
C19'—C20'—H20F	109.5
C16—C11—C12—O4	−177.48 (16)	C6—C1—C2—O1	−178.96 (15)
C17—C11—C12—O4	0.5 (3)	C7—C1—C2—O1	1.2 (3)
C16—C11—C12—C13	2.4 (3)	C6—C1—C2—C3	1.8 (3)
C17—C11—C12—C13	−179.56 (18)	C7—C1—C2—C3	−178.12 (18)
O4—C12—C13—C14	178.5 (2)	O1—C2—C3—C4	179.65 (19)
C11—C12—C13—C14	−1.4 (3)	C1—C2—C3—C4	−1.1 (3)
C12—C13—C14—C15	−0.2 (4)	C2—C3—C4—C5	−0.4 (3)
C13—C14—C15—C16	0.7 (4)	C3—C4—C5—C6	1.1 (3)
C14—C15—C16—O5	−179.57 (19)	C4—C5—C6—O2	−179.74 (18)
C14—C15—C16—C11	0.4 (3)	C4—C5—C6—C1	−0.4 (3)
C12—C11—C16—O5	178.04 (16)	C2—C1—C6—O2	178.36 (15)
C17—C11—C16—O5	0.2 (3)	C7—C1—C6—O2	−1.8 (3)
C12—C11—C16—C15	−2.0 (3)	C2—C1—C6—C5	−1.0 (3)
C17—C11—C16—C15	−179.84 (17)	C7—C1—C6—C5	178.83 (17)
C12—C11—C17—O6	−2.5 (3)	C6—C1—C7—O3	175.76 (17)
C16—C11—C17—O6	175.33 (17)	C2—C1—C7—O3	−4.4 (3)
C12—C11—C17—C18	176.3 (2)	C6—C1—C7—C8	−4.4 (3)
C16—C11—C17—C18	−5.9 (3)	C2—C1—C7—C8	175.47 (16)
O6—C17—C18—C19	31.2 (4)	O3—C7—C8—C9	3.5 (3)
C11—C17—C18—C19	−147.6 (3)	C1—C7—C8—C9	−176.29 (17)
C17—C18—C19—C20	56.5 (9)	C7—C8—C9—C10	−175.12 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O6	0.90 (2)	1.66 (2)	2.498 (2)	153 (2)
O5—H5···O1	0.85 (2)	1.90 (2)	2.744 (2)	169 (2)
O1—H1···O3	0.96 (3)	1.58 (3)	2.460 (2)	151 (3)
O2—H2···O6^i	0.90 (3)	1.83 (3)	2.712 (2)	166 (2)

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