4-Acetyl­resorcinol

The mol­ecule of the title compound [1-(2,4-dihydroxy­phenyl)­ethanone], C₈H₈O₃, is planar except for the methyl H atoms. One intra­molecular O—H...O hydrogen bond and a second inter­molecular O—H...O inter­action link the mol­ecules into chains as seen down the 010 face. The distance between the sheets is 3.049 Å at its closest and 3.262 Å at its farthest.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.115
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT707_ALERT_1_A D...A   Calc  4.7419(14), Rep     2.56(4), Dev..    1558.50 Sigma
              O2   -O1      1.555   1.555
PLAT707_ALERT_1_A D...A   Calc 10.4392(15), Rep     2.65(4), Dev..    5192.80 Sigma
              O3   -O2      1.555   4.466
PLAT725_ALERT_1_A D-H     Calc     6.55000, Rep     0.82000 Dev...       5.73 Ang.
              O3   -H1      1.555   1.555
PLAT726_ALERT_1_A H...A   Calc     5.40000, Rep     1.83900 Dev...       3.56 Ang.
              H2A  -O1      1.555   1.555
PLAT726_ALERT_1_A H...A   Calc     3.89000, Rep     1.92200 Dev...       1.97 Ang.
              H1   -O2      1.555   4.466
PLAT728_ALERT_1_A D-H..A  Calc       34.00, Rep      146.23 Dev...     112.23 Deg.
              O2   -H2A  -O1      1.555   1.555   1.555
PLAT728_ALERT_1_A D-H..A  Calc      176.00, Rep      147.77 Dev...      28.23 Deg.
              O3   -H1   -O2      1.555   1.555   4.466
PLAT737_ALERT_1_A D...A   Calc  4.7419(14), Rep     2.56(4) ......       9.90 su-Ra
              O2   -O1      1.555   1.555
PLAT737_ALERT_1_A D...A   Calc 10.4392(15), Rep     2.65(4) ......       9.90 su-Ra
              O3   -O2      1.555   4.466

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

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

  10 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
   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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S1. Comment

The title compound, (I, Fig. 1), was formed in a reaction mixture containing resorcinol, 3,4-pyridine dicarboxlyic acid anhydride, acetic acid and sulfuric acid where the original intent was to prepare a fluoroscein derivative containing pyridine for use as a chelating ligand which would allow for detection of metal ions at very low concentrations. The title compound is currently being used as a starting material for synthesis of new chelating ligands. There have been several derivatives of resorcinol published in the literature (Fronczek et al., 1987; Kokila et al., 1992; Liebich, 1979; Li et al., 2005; van Rooyen & Breytenbach, 1988). The compound most similiar to (I) (Kokila et al., 1992) has two acetyl groups found in the 4 and 6 positions. However, it differs from (I) in that it has two intramolecular O—H···O hydrogen bonds and no intermolecular interactions. In (I), in addition to the O3 ··· O4 intramolecular H-bond there is an intermolecular H-bod between O2 and O3 that links the molecules inttoo sheets which can be seen by viewing the unit cell down the 010 face. The distance between the sheets is 3.049 Å at its closest and 3.262 Å at its fartherest.

Related literature

For related literature, see: Fronczek et al. (1987); Kokila et al. (1992); Liebich (1979); Li et al. (2005); van Rooyen & Breytenbach (1988).

S2. Experimental

The title compound was synthesized by refluxing 0.11 g (0.75 mmol) of 3,4-Pyridinedicarboxylic anhydride and 0.19 g (1.72 mmol) of resorcinol in 15:1 Glacial Acetic Acid:Water for 30 minutes. Added 250.7 µL of con. H₂SO₄ and 10 ml of water. Continued relux overnight. Allowed the solution to cool. Suitable crystals of the title compound were found on the bottom.

S3. Refinement

All non-hydrogen atoms were refined using anisotropic thermal parameters. All hydrogen atoms were included at idealized positions and not refined.

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Bruker, 2006); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2006).

Figures

Fig. 1. ORTEP drawing with 50% elipsoids.

1-(2,4-dihydroxyphenyl)ethanone

Crystal data

C8H8O3	F(000) = 320
Mr = 152.14	Dx = 1.417 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3391 reflections
a = 7.1325 (3) Å	θ = 2.9–26.7°
b = 13.7067 (5) Å	µ = 0.11 mm^−1
c = 7.2998 (3) Å	T = 296 K
β = 92.369 (2)°	Block, red
V = 713.04 (5) Å^3	0.50 × 0.32 × 0.24 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	1394 independent reflections
Radiation source: fine-focus sealed tube	1112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
φ and ω scans	θmax = 26.0°, θmin = 2.9°
Absorption correction: numerical (SADABS; Bruker, 2006)	h = −8→8
Tmin = 0.948, Tmax = 0.974	k = −16→16
11606 measured reflections	l = −8→8

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) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 0.1744P] where P = (Fo^2 + 2Fc^2)/3
1394 reflections	(Δ/σ)max < 0.001
103 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.21 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
C8	1.3101 (2)	0.43113 (11)	0.6235 (2)	0.0320 (4)
H8A	1.4239	0.4138	0.5657	0.048*
H8B	1.3391	0.4725	0.7270	0.048*
H8C	1.2285	0.4652	0.5374	0.048*
C7	1.2146 (2)	0.34057 (10)	0.68663 (18)	0.0249 (3)
C4	1.03441 (18)	0.34595 (9)	0.77170 (17)	0.0212 (3)
C3	0.94218 (19)	0.26014 (9)	0.82921 (17)	0.0214 (3)
C2	0.77058 (19)	0.26558 (10)	0.91087 (17)	0.0226 (3)
H2	0.7107	0.2090	0.9473	0.027*
C1	0.68871 (19)	0.35572 (9)	0.93794 (18)	0.0235 (3)
C6	0.7743 (2)	0.44146 (10)	0.87870 (19)	0.0259 (3)
H6	0.7165	0.5016	0.8941	0.031*
C5	0.94371 (19)	0.43583 (9)	0.79787 (17)	0.0239 (3)
H5	1.0005	0.4929	0.7592	0.029*
O3	1.29189 (14)	0.26013 (7)	0.66509 (14)	0.0320 (3)
O2	1.01829 (14)	0.17102 (7)	0.80826 (13)	0.0280 (3)
H2A	1.1171	0.1762	0.7555	0.042*
O1	0.52510 (14)	0.36696 (7)	1.02242 (15)	0.0320 (3)
H1	0.4859	0.3134	1.0531	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.0231 (8)	0.0356 (8)	0.0378 (8)	−0.0037 (6)	0.0075 (6)	0.0033 (6)
C7	0.0216 (8)	0.0291 (8)	0.0240 (7)	0.0015 (6)	0.0018 (5)	−0.0012 (5)
C4	0.0196 (8)	0.0216 (7)	0.0224 (7)	−0.0007 (5)	0.0018 (5)	0.0002 (5)
C3	0.0234 (7)	0.0196 (7)	0.0212 (6)	0.0027 (5)	0.0003 (5)	−0.0014 (5)
C2	0.0238 (8)	0.0201 (7)	0.0242 (7)	−0.0032 (5)	0.0025 (5)	0.0014 (5)
C1	0.0202 (7)	0.0269 (7)	0.0236 (7)	0.0009 (5)	0.0034 (5)	−0.0011 (5)
C6	0.0248 (8)	0.0201 (7)	0.0330 (7)	0.0037 (5)	0.0035 (6)	−0.0005 (6)
C5	0.0246 (8)	0.0192 (7)	0.0280 (7)	−0.0017 (5)	0.0020 (5)	0.0010 (5)
O3	0.0270 (6)	0.0319 (6)	0.0377 (6)	0.0052 (4)	0.0101 (4)	−0.0016 (4)
O2	0.0295 (6)	0.0200 (5)	0.0352 (6)	0.0038 (4)	0.0091 (4)	−0.0004 (4)
O1	0.0258 (6)	0.0273 (6)	0.0440 (6)	0.0021 (4)	0.0158 (5)	0.0019 (5)

Geometric parameters (Å, º)

C8—C7	1.4976 (19)	C2—C1	1.3842 (18)
C8—H8A	0.9600	C2—H2	0.9300
C8—H8B	0.9600	C1—O1	1.3510 (17)
C8—H8C	0.9600	C1—C6	1.4008 (19)
C7—O3	1.2455 (17)	C6—C5	1.369 (2)
C7—C4	1.4522 (19)	C6—H6	0.9300
C4—C5	1.4081 (18)	C5—H5	0.9300
C4—C3	1.4196 (18)	O2—H2A	0.8200
C3—O2	1.3480 (15)	O1—H1	0.8200
C3—C2	1.3853 (19)
C7—C8—H8A	109.5	C1—C2—C3	119.66 (12)
C7—C8—H8B	109.5	C1—C2—H2	120.2
H8A—C8—H8B	109.5	C3—C2—H2	120.2
C7—C8—H8C	109.5	O1—C1—C2	122.98 (12)
H8A—C8—H8C	109.5	O1—C1—C6	116.15 (11)
H8B—C8—H8C	109.5	C2—C1—C6	120.87 (13)
O3—C7—C4	120.21 (12)	C5—C6—C1	119.30 (12)
O3—C7—C8	119.04 (13)	C5—C6—H6	120.4
C4—C7—C8	120.75 (12)	C1—C6—H6	120.4
C5—C4—C3	117.62 (12)	C6—C5—C4	121.77 (12)
C5—C4—C7	121.47 (12)	C6—C5—H5	119.1
C3—C4—C7	120.90 (12)	C4—C5—H5	119.1
O2—C3—C2	117.69 (12)	C3—O2—H2A	109.5
O2—C3—C4	121.57 (12)	C1—O1—H1	109.5
C2—C3—C4	120.74 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.84	2.56 (4)	146
O3—H1···O2^i	0.82	1.92	2.65 (4)	148

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