7-Hydr­oxy-4,6-dimethyl-3H-isobenzofuran-1-one

The structure of the title compound, C₁₀H₁₀O₃, a colourless lump metabolite isolated from Diaporthe phaseolorum, was determined by X-ray analysis. The mol­ecular packing in the crystal structure is stabilized by weak O—H...O=C hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.061
• wR factor = 0.161
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
SHFSU01_ALERT_2_B  The absolute value of parameter shift to su ratio > 0.10
            Absolute value of the parameter shift to su ratio given   0.154
            Additional refinement cycles may be required.
PLAT080_ALERT_2_B Maximum Shift/Error ............................       0.15

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   1 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
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

7-Hydroxy-4,6-dimethyl-3H-isobenzofuran-1-one

Crystal data

C10H10O3	F(000) = 752
Mr = 178.18	Dx = 1.396 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3244 reflections
a = 14.362 (5) Å	θ = 2.8–27.4°
b = 8.220 (3) Å	µ = 0.10 mm^−1
c = 14.360 (2) Å	T = 273 K
V = 1695.5 (9) Å^3	Chunk, colourless
Z = 8	0.38 × 0.25 × 0.11 mm

Data collection

Bruker APEX area-detector diffractometer	1750 independent reflections
Radiation source: fine-focus sealed tube	1577 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→18
Tmin = 0.962, Tmax = 0.989	k = −5→10
8712 measured reflections	l = −18→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0779P)^2 + 0.9444P] where P = (Fo^2 + 2Fc^2)/3
1750 reflections	(Δ/σ)max = 0.154
120 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	−0.01139 (15)	0.10792 (19)	0.41702 (13)	0.0612 (6)
C1	0.01894 (16)	0.2376 (3)	0.39665 (15)	0.0401 (5)
O2	0.00197 (12)	0.30531 (18)	0.31362 (10)	0.0488 (5)
C2	0.07657 (13)	0.3470 (2)	0.44961 (14)	0.0323 (5)
O3	0.09450 (11)	0.19702 (17)	0.59115 (11)	0.0452 (4)
H3A	0.0617	0.1326	0.5624	0.068*
C3	0.11031 (13)	0.3286 (2)	0.53837 (14)	0.0330 (5)
C4	0.16383 (14)	0.4537 (3)	0.57452 (15)	0.0369 (5)
C5	0.17852 (14)	0.5892 (3)	0.52042 (16)	0.0404 (5)
H5A	0.2140	0.6729	0.5457	0.048*
C6	0.14476 (14)	0.6102 (2)	0.43185 (15)	0.0381 (5)
C7	0.09345 (13)	0.4832 (2)	0.39740 (14)	0.0335 (5)
C8	0.04661 (17)	0.4612 (3)	0.30713 (15)	0.0431 (5)
H8A	0.0011	0.5466	0.2967	0.052*
H8B	0.0914	0.4626	0.2566	0.052*
C9	0.20502 (18)	0.4407 (3)	0.66937 (17)	0.0526 (6)
H9A	0.2161	0.5478	0.6937	0.079*
H9B	0.2628	0.3823	0.6660	0.079*
H9C	0.1627	0.3837	0.7095	0.079*
C10	0.16237 (19)	0.7624 (3)	0.37762 (19)	0.0565 (7)
H10A	0.1258	0.7610	0.3217	0.085*
H10B	0.2272	0.7689	0.3618	0.085*
H10C	0.1454	0.8551	0.4146	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0941 (14)	0.0364 (9)	0.0531 (11)	−0.0225 (9)	−0.0153 (9)	0.0031 (7)
C1	0.0529 (13)	0.0337 (10)	0.0337 (11)	−0.0017 (9)	−0.0049 (9)	−0.0036 (8)
O2	0.0712 (11)	0.0427 (9)	0.0327 (9)	−0.0105 (8)	−0.0135 (7)	−0.0006 (6)
C2	0.0341 (10)	0.0305 (9)	0.0322 (10)	0.0012 (8)	0.0012 (8)	−0.0030 (8)
O3	0.0595 (10)	0.0380 (8)	0.0381 (9)	−0.0092 (7)	−0.0104 (7)	0.0063 (6)
C3	0.0330 (9)	0.0329 (10)	0.0331 (10)	0.0019 (8)	−0.0005 (8)	0.0002 (8)
C4	0.0348 (10)	0.0394 (11)	0.0367 (11)	0.0012 (8)	−0.0045 (8)	−0.0045 (9)
C5	0.0351 (10)	0.0375 (11)	0.0486 (13)	−0.0069 (8)	−0.0050 (9)	−0.0080 (9)
C6	0.0358 (10)	0.0348 (11)	0.0439 (12)	−0.0034 (8)	0.0036 (9)	0.0006 (9)
C7	0.0335 (10)	0.0345 (10)	0.0325 (10)	0.0030 (8)	0.0046 (8)	0.0005 (8)
C8	0.0545 (13)	0.0419 (12)	0.0328 (11)	−0.0051 (10)	−0.0015 (9)	0.0028 (9)
C9	0.0576 (14)	0.0547 (14)	0.0455 (14)	−0.0042 (12)	−0.0177 (11)	−0.0035 (11)
C10	0.0650 (16)	0.0452 (13)	0.0593 (16)	−0.0158 (11)	0.0012 (13)	0.0105 (12)

Geometric parameters (Å, º)

O1—C1	1.188 (3)	C5—H5A	0.9300
C1—O2	1.338 (3)	C6—C7	1.370 (3)
C1—C2	1.439 (3)	C6—C10	1.496 (3)
O2—C8	1.436 (3)	C7—C8	1.472 (3)
C2—C7	1.369 (3)	C8—H8A	0.9700
C2—C3	1.372 (3)	C8—H8B	0.9700
O3—C3	1.340 (2)	C9—H9A	0.9600
O3—H3A	0.8200	C9—H9B	0.9600
C3—C4	1.385 (3)	C9—H9C	0.9600
C4—C5	1.374 (3)	C10—H10A	0.9600
C4—C9	1.489 (3)	C10—H10B	0.9600
C5—C6	1.372 (3)	C10—H10C	0.9600
O1—C1—O2	121.7 (2)	C2—C7—C8	107.53 (18)
O1—C1—C2	129.9 (2)	C6—C7—C8	131.10 (19)
O2—C1—C2	108.42 (18)	O2—C8—C7	104.85 (16)
C1—O2—C8	110.34 (16)	O2—C8—H8A	110.8
C7—C2—C3	122.44 (18)	C7—C8—H8A	110.8
C7—C2—C1	108.85 (18)	O2—C8—H8B	110.8
C3—C2—C1	128.69 (19)	C7—C8—H8B	110.8
C3—O3—H3A	109.5	H8A—C8—H8B	108.9
O3—C3—C2	123.69 (18)	C4—C9—H9A	109.5
O3—C3—C4	118.77 (18)	C4—C9—H9B	109.5
C2—C3—C4	117.54 (18)	H9A—C9—H9B	109.5
C5—C4—C3	118.37 (19)	C4—C9—H9C	109.5
C5—C4—C9	120.96 (19)	H9A—C9—H9C	109.5
C3—C4—C9	120.7 (2)	H9B—C9—H9C	109.5
C6—C5—C4	124.86 (19)	C6—C10—H10A	109.5
C6—C5—H5A	117.6	C6—C10—H10B	109.5
C4—C5—H5A	117.6	H10A—C10—H10B	109.5
C7—C6—C5	115.42 (19)	C6—C10—H10C	109.5
C7—C6—C10	122.7 (2)	H10A—C10—H10C	109.5
C5—C6—C10	121.9 (2)	H10B—C10—H10C	109.5
C2—C7—C6	121.36 (19)
O1—C1—O2—C8	−180.0 (2)	C9—C4—C5—C6	178.8 (2)
C2—C1—O2—C8	−0.1 (2)	C4—C5—C6—C7	−0.4 (3)
O1—C1—C2—C7	−179.5 (2)	C4—C5—C6—C10	179.0 (2)
O2—C1—C2—C7	0.6 (2)	C3—C2—C7—C6	−0.6 (3)
O1—C1—C2—C3	−0.8 (4)	C1—C2—C7—C6	178.25 (18)
O2—C1—C2—C3	179.40 (19)	C3—C2—C7—C8	−179.70 (19)
C7—C2—C3—O3	179.68 (18)	C1—C2—C7—C8	−0.8 (2)
C1—C2—C3—O3	1.0 (3)	C5—C6—C7—C2	1.0 (3)
C7—C2—C3—C4	−0.5 (3)	C10—C6—C7—C2	−178.3 (2)
C1—C2—C3—C4	−179.2 (2)	C5—C6—C7—C8	179.9 (2)
O3—C3—C4—C5	−179.05 (18)	C10—C6—C7—C8	0.5 (4)
C2—C3—C4—C5	1.1 (3)	C1—O2—C8—C7	−0.4 (2)
O3—C3—C4—C9	1.5 (3)	C2—C7—C8—O2	0.7 (2)
C2—C3—C4—C9	−178.3 (2)	C6—C7—C8—O2	−178.2 (2)
C3—C4—C5—C6	−0.7 (3)