2,4-Diacetyl­benzene-1,3-diol

In the crystal structure of the title compound, C₁₀H₁₀O₄, there are two independent mol­ecules in the asymmetric unit. Each mol­ecule is characterized by intra­molecular O—H...O hydrogen bonding. The crystal structure is stabilized by inter­molecular C—H...O hydrogen bonds and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.064
• wR factor = 0.149
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.17 Ratio
PLAT391_ALERT_3_B Deviating Methyl C8      H-C-H Bond Angle ......      99.00 Deg.

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O2B    -   H2Y    ...       1.02 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O4B    -   H4Y    ...       1.06 Ang.
PLAT390_ALERT_3_C Deviating Methyl C10     X-C-H Bond Angle ......     102.00 Deg.
PLAT708_ALERT_1_C D-H..A  Calc      154(4), Rep      146(4), Dev..       2.00 Sigma
              O2B  -H2Y  -O1B     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 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
   6 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: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,4-Diacetylbenzene-1,3-diol

Crystal data

C10H10O4	F(000) = 816
Mr = 194.18	Dx = 1.446 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18514 reflections
a = 6.9666 (3) Å	θ = 3.4–26.0°
b = 10.6786 (7) Å	µ = 0.11 mm^−1
c = 24.0792 (14) Å	T = 173 K
β = 95.215 (4)°	Needle, colourless
V = 1783.92 (17) Å^3	0.1 × 0.05 × 0.02 mm
Z = 8

Data collection

Nonius KappaCCD area-detector diffractometer	2097 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.082
Graphite monochromator	θmax = 26.0°, θmin = 3.5°
Detector resolution: 9 pixels mm^-1	h = −8→8
φ and ω scans	k = −13→10
9562 measured reflections	l = −29→29
3482 independent reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0505P)^2 + 0.8082P] where P = (Fo^2 + 2Fc^2)/3
3482 reflections	(Δ/σ)max < 0.001
333 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. IR (KBr, v, cm^-1): 3252 (br, O—H), 1630, 1640, 1507, 1447, 1372, 1322, 1275. ¹H-NMR (400 MHz, DMSO– d6, 298 K, TMS): δ 2.2 (3H, s, CH₃), 2.8 (3H, s, CH₃), 6.4 (1H, d, aromatic), 8.5 (1H, d, aromatic), 12.7 (1H, s, OH), 12.9 (1H, s, OH).

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
O1	0.1763 (3)	0.6426 (2)	0.05237 (8)	0.0343 (5)
H1X	0.177 (5)	0.714 (4)	0.0343 (15)	0.082 (13)*
O2	0.1363 (3)	0.35739 (19)	0.16600 (8)	0.0423 (6)
O3	0.1054 (3)	0.5180 (2)	0.23973 (8)	0.0402 (6)
H3X	0.125 (6)	0.440 (4)	0.2193 (18)	0.106 (16)*
O4	0.1694 (3)	0.87242 (19)	0.03130 (8)	0.0426 (6)
C1	0.1229 (3)	0.7964 (3)	0.12072 (10)	0.0287 (7)
C2	0.1431 (3)	0.6702 (3)	0.10482 (10)	0.0264 (7)
C3	0.1304 (3)	0.5714 (3)	0.14358 (10)	0.0267 (6)
C4	0.1069 (3)	0.6048 (3)	0.19934 (11)	0.0316 (7)
C5	0.0835 (4)	0.7297 (3)	0.21518 (12)	0.0346 (7)
H5	0.057 (3)	0.747 (3)	0.2539 (11)	0.040 (8)*
C6	0.0909 (4)	0.8223 (3)	0.17652 (12)	0.0328 (7)
H6	0.080 (4)	0.905 (3)	0.1855 (11)	0.036 (8)*
C7	0.1351 (4)	0.8967 (3)	0.08014 (12)	0.0345 (7)
C8	0.1052 (6)	1.0311 (3)	0.09562 (17)	0.0505 (9)
H8C	0.104 (6)	1.078 (5)	0.061 (2)	0.121 (17)*
H8B	0.205 (7)	1.062 (5)	0.126 (2)	0.15 (2)*
H8A	−0.010 (7)	1.038 (4)	0.116 (2)	0.119 (17)*
C9	0.1384 (4)	0.4386 (3)	0.12870 (11)	0.0322 (7)
C10	0.1418 (5)	0.3937 (3)	0.07027 (13)	0.0402 (8)
H10C	0.128 (5)	0.303 (4)	0.0744 (14)	0.076 (12)*
H10B	0.265 (4)	0.416 (3)	0.0552 (12)	0.051 (9)*
H10A	0.041 (4)	0.430 (3)	0.0458 (12)	0.050 (9)*
O1B	0.3368 (3)	−0.16272 (19)	0.44189 (8)	0.0416 (6)
O2B	0.3394 (3)	0.0705 (2)	0.45077 (8)	0.0371 (5)
H2Y	0.332 (6)	−0.023 (4)	0.4582 (17)	0.105 (15)*
O3B	0.3839 (3)	0.4167 (2)	0.37683 (9)	0.0460 (6)
O4B	0.4039 (3)	0.3096 (2)	0.28639 (9)	0.0428 (6)
H4Y	0.394 (5)	0.380 (4)	0.3170 (18)	0.101 (14)*
C1B	0.3701 (3)	−0.0332 (3)	0.36456 (11)	0.0277 (6)
C2B	0.3600 (3)	0.0783 (3)	0.39647 (10)	0.0269 (6)
C3B	0.3735 (3)	0.1978 (3)	0.37175 (10)	0.0271 (6)
C4B	0.3922 (4)	0.2006 (3)	0.31344 (11)	0.0318 (7)
C5B	0.3995 (4)	0.0921 (3)	0.28191 (12)	0.0362 (7)
H5B	0.414 (3)	0.098 (3)	0.2437 (11)	0.033 (7)*
C6B	0.3900 (4)	−0.0220 (3)	0.30713 (12)	0.0335 (7)
H6B	0.397 (4)	−0.097 (3)	0.2856 (11)	0.034 (8)*
C7B	0.3627 (4)	−0.1548 (3)	0.39150 (12)	0.0315 (7)
C8B	0.3894 (6)	−0.2733 (3)	0.36007 (16)	0.0475 (9)
H8F	0.289 (5)	−0.286 (4)	0.3299 (17)	0.096 (14)*
H8E	0.510 (5)	−0.270 (3)	0.3405 (14)	0.072 (11)*
H8D	0.402 (5)	−0.347 (4)	0.3881 (16)	0.091 (13)*
C9B	0.3668 (4)	0.3161 (3)	0.40242 (12)	0.0343 (7)
C10B	0.3426 (5)	0.3249 (3)	0.46319 (13)	0.0390 (8)
H10F	0.226 (4)	0.281 (3)	0.4713 (11)	0.049 (9)*
H10E	0.451 (4)	0.283 (3)	0.4866 (12)	0.054 (9)*
H10D	0.339 (5)	0.416 (4)	0.4726 (14)	0.072 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0429 (12)	0.0347 (13)	0.0260 (11)	0.0006 (10)	0.0079 (8)	0.0008 (10)
O2	0.0541 (13)	0.0339 (13)	0.0401 (13)	0.0006 (11)	0.0103 (9)	0.0066 (11)
O3	0.0477 (12)	0.0462 (15)	0.0278 (11)	0.0045 (11)	0.0091 (9)	0.0082 (10)
O4	0.0530 (13)	0.0379 (13)	0.0382 (13)	0.0010 (11)	0.0112 (10)	0.0074 (10)
C1	0.0236 (14)	0.0309 (18)	0.0319 (16)	−0.0023 (13)	0.0037 (11)	0.0011 (13)
C2	0.0193 (13)	0.0355 (19)	0.0248 (15)	−0.0011 (12)	0.0032 (10)	−0.0003 (13)
C3	0.0224 (13)	0.0325 (18)	0.0256 (15)	0.0010 (12)	0.0042 (10)	0.0015 (13)
C4	0.0236 (14)	0.0419 (19)	0.0297 (16)	0.0006 (13)	0.0044 (11)	0.0057 (14)
C5	0.0309 (15)	0.047 (2)	0.0263 (15)	0.0026 (14)	0.0034 (11)	−0.0056 (15)
C6	0.0286 (15)	0.033 (2)	0.0369 (17)	0.0011 (14)	0.0023 (12)	−0.0050 (15)
C7	0.0288 (15)	0.0350 (19)	0.0397 (18)	−0.0012 (13)	0.0042 (12)	0.0028 (15)
C8	0.072 (3)	0.028 (2)	0.053 (2)	0.0016 (18)	0.014 (2)	0.0009 (17)
C9	0.0250 (14)	0.0380 (19)	0.0338 (16)	0.0029 (13)	0.0043 (11)	0.0044 (14)
C10	0.054 (2)	0.033 (2)	0.0341 (18)	0.0025 (17)	0.0074 (15)	0.0004 (15)
O1B	0.0519 (13)	0.0350 (13)	0.0389 (12)	−0.0015 (10)	0.0099 (9)	0.0066 (10)
O2B	0.0493 (12)	0.0343 (13)	0.0291 (11)	0.0003 (10)	0.0117 (9)	0.0009 (9)
O3B	0.0567 (14)	0.0315 (13)	0.0507 (14)	0.0002 (11)	0.0092 (10)	0.0051 (11)
O4B	0.0455 (13)	0.0424 (14)	0.0416 (13)	0.0003 (11)	0.0099 (9)	0.0153 (11)
C1B	0.0233 (14)	0.0291 (17)	0.0312 (15)	0.0007 (13)	0.0044 (11)	0.0004 (13)
C2B	0.0217 (13)	0.0358 (19)	0.0237 (14)	0.0030 (13)	0.0049 (10)	0.0033 (13)
C3B	0.0231 (14)	0.0291 (17)	0.0295 (15)	0.0012 (12)	0.0048 (10)	0.0021 (13)
C4B	0.0261 (14)	0.0359 (18)	0.0334 (16)	0.0003 (13)	0.0029 (11)	0.0089 (14)
C5B	0.0377 (17)	0.044 (2)	0.0273 (16)	0.0015 (15)	0.0079 (12)	0.0042 (16)
C6B	0.0293 (15)	0.040 (2)	0.0315 (17)	0.0015 (14)	0.0062 (12)	−0.0049 (15)
C7B	0.0263 (14)	0.0336 (19)	0.0344 (17)	−0.0011 (13)	0.0019 (12)	0.0007 (14)
C8B	0.059 (2)	0.032 (2)	0.050 (2)	0.0050 (18)	0.0013 (18)	−0.0041 (17)
C9B	0.0264 (15)	0.034 (2)	0.0435 (18)	0.0002 (13)	0.0069 (12)	0.0051 (15)
C10B	0.0427 (19)	0.035 (2)	0.0391 (18)	0.0002 (17)	0.0037 (14)	−0.0032 (15)

Geometric parameters (Å, º)

O1—C2	1.337 (3)	O1B—C7B	1.246 (3)
O1—H1X	0.88 (4)	O2B—C2B	1.331 (3)
O2—C9	1.250 (3)	O2B—H2Y	1.01 (5)
O3—C4	1.345 (3)	O3B—C9B	1.249 (3)
O3—H3X	0.98 (4)	O4B—C4B	1.339 (3)
O4—C7	1.249 (3)	O4B—H4Y	1.06 (4)
C1—C6	1.409 (4)	C1B—C6B	1.407 (4)
C1—C2	1.412 (4)	C1B—C2B	1.422 (4)
C1—C7	1.458 (4)	C1B—C7B	1.456 (4)
C2—C3	1.417 (4)	C2B—C3B	1.415 (4)
C3—C4	1.413 (4)	C3B—C4B	1.422 (3)
C3—C9	1.464 (4)	C3B—C9B	1.466 (4)
C4—C5	1.400 (4)	C4B—C5B	1.389 (4)
C5—C6	1.362 (4)	C5B—C6B	1.366 (4)
C5—H5	0.98 (3)	C5B—H5B	0.94 (3)
C6—H6	0.92 (3)	C6B—H6B	0.96 (3)
C7—C8	1.502 (4)	C7B—C8B	1.494 (4)
C8—H8C	0.98 (5)	C8B—H8F	0.97 (4)
C8—H8B	1.03 (5)	C8B—H8E	1.00 (3)
C8—H8A	0.99 (5)	C8B—H8D	1.03 (4)
C9—C10	1.489 (4)	C9B—C10B	1.491 (4)
C10—H10C	0.98 (4)	C10B—H10F	0.97 (3)
C10—H10B	0.99 (3)	C10B—H10E	1.01 (3)
C10—H10A	0.96 (3)	C10B—H10D	1.00 (4)
C2—O1—H1X	107 (2)	C2B—O2B—H2Y	104 (2)
C4—O3—H3X	102 (2)	C4B—O4B—H4Y	105 (2)
C6—C1—C2	118.3 (3)	C6B—C1B—C2B	118.3 (3)
C6—C1—C7	121.2 (3)	C6B—C1B—C7B	121.6 (3)
C2—C1—C7	120.5 (2)	C2B—C1B—C7B	120.1 (2)
O1—C2—C1	119.8 (2)	O2B—C2B—C3B	119.2 (2)
O1—C2—C3	119.0 (2)	O2B—C2B—C1B	119.5 (2)
C1—C2—C3	121.2 (2)	C3B—C2B—C1B	121.3 (2)
C4—C3—C2	117.2 (3)	C2B—C3B—C4B	116.7 (2)
C4—C3—C9	119.2 (2)	C2B—C3B—C9B	124.0 (2)
C2—C3—C9	123.6 (2)	C4B—C3B—C9B	119.3 (3)
O3—C4—C5	116.8 (3)	O4B—C4B—C5B	116.9 (2)
O3—C4—C3	121.5 (3)	O4B—C4B—C3B	120.9 (3)
C5—C4—C3	121.7 (3)	C5B—C4B—C3B	122.2 (3)
C6—C5—C4	119.5 (3)	C6B—C5B—C4B	119.7 (3)
C6—C5—H5	122.5 (17)	C6B—C5B—H5B	120.8 (17)
C4—C5—H5	118.0 (17)	C4B—C5B—H5B	119.5 (17)
C5—C6—C1	121.9 (3)	C5B—C6B—C1B	121.7 (3)
C5—C6—H6	122.2 (17)	C5B—C6B—H6B	120.1 (16)
C1—C6—H6	115.9 (17)	C1B—C6B—H6B	118.2 (17)
O4—C7—C1	120.4 (3)	O1B—C7B—C1B	120.6 (3)
O4—C7—C8	118.4 (3)	O1B—C7B—C8B	118.2 (3)
C1—C7—C8	121.2 (3)	C1B—C7B—C8B	121.2 (3)
C7—C8—H8C	105 (3)	C7B—C8B—H8F	113 (2)
C7—C8—H8B	113 (3)	C7B—C8B—H8E	111 (2)
H8C—C8—H8B	114 (4)	H8F—C8B—H8E	103 (3)
C7—C8—H8A	110 (3)	C7B—C8B—H8D	109 (2)
H8C—C8—H8A	117 (4)	H8F—C8B—H8D	113 (3)
H8B—C8—H8A	98 (4)	H8E—C8B—H8D	108 (3)
O2—C9—C3	119.5 (2)	O3B—C9B—C3B	118.9 (2)
O2—C9—C10	117.2 (3)	O3B—C9B—C10B	117.0 (3)
C3—C9—C10	123.2 (3)	C3B—C9B—C10B	124.0 (3)
C9—C10—H10C	102 (2)	C9B—C10B—H10F	109.7 (17)
C9—C10—H10B	111.0 (17)	C9B—C10B—H10E	112.1 (17)
H10C—C10—H10B	112 (3)	H10F—C10B—H10E	106 (2)
C9—C10—H10A	112.1 (18)	C9B—C10B—H10D	107 (2)
H10C—C10—H10A	113 (3)	H10F—C10B—H10D	113 (3)
H10B—C10—H10A	107 (2)	H10E—C10B—H10D	110 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1X···O4	0.88 (4)	1.69 (4)	2.506 (3)	153 (4)
O2B—H2Y···O1B	1.01 (4)	1.55 (4)	2.499 (3)	146 (4)
O3—H3X···O2	0.98 (4)	1.57 (4)	2.492 (3)	155 (4)
O4B—H4Y···O3B	1.06 (4)	1.50 (4)	2.475 (3)	150 (4)
C6B—H6B···O4B^i	0.96 (3)	2.52 (3)	3.310 (4)	140 (2)
C8B—H8D···O3B^ii	1.04 (4)	2.54 (4)	3.336 (4)	133 (3)
C10B—H10E···O1B^iii	1.01 (3)	2.52 (3)	3.505 (4)	167 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1, −y, −z+1.