4′-Hydro­xy-3′-methoxy­aceto­phenone (acetovanillone)

The crystal structure of acetovanillone, C₉H₁₀O₃, has been determined at 173 (1) K. All the C and O atoms are essentially coplanar, and the mol­ecules pack in parallel planes as a result of intermolecular hydrogen bonds (C—H...O and O—H...O).

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](Please check) = 0.000 Å
• H-atom completeness 91%
• R factor = 0.041
• wR factor = 0.122
• Data-to-parameter ratio = 15.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



ABSTM_02  Alert B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
          Tmin and Tmax reported:      0.703     1.000
          Tmin' and Tmax expected:      0.949     0.990
          RR' =      0.734
          Please check that your absorption correction is appropriate.

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C9 H10 O3
          Atom count from the _atom_site data:  C9 H9 O3

CELLZ_01
         From the CIF: _cell_formula_units_Z    4
         From the CIF: _chemical_formula_sum  C9 H10 O3
         TEST: Compare cell contents of formula and atom_site data
         WARNING: Unexpected atom type is in site list: HB
         WARNING: Formula and atom_type_symbol element names mismatch.

         atom    Z*formula  cif sites diff
         C         36.00     36.00    0.00
         H         40.00     36.00    4.00
         O         12.00     12.00    0.00
          WARNING: Site labels do not match formula elements
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

S1. Comment

The title compound, (I), first synthesized in 1949 (Berlin et al., 1949), is a popular model compound used to represent ketonic moieties in lignin; it has recently been used as a substrate to test hydrogenation activity of several platinum metal-based systems (Hu & James, 2002). The molecular structure of (I) is shown in Fig. 1, and selected geometric parameter are listed in Table 1.

Four different C—O bond lengths are found in the molecule: C8—O3 1.230 (2) Å, C2—O2 1.372 (2) Å, C1—O1 1.353 (2) Å and C7—O2 1.431 (2) Å. The orientations of the carbonyl, methyl and methoxy groups with respect to the aromatic ring are defined by the torsion angles O1—C1—C2—C3 − 179.3 (1)°, O2—C2—C1—C6 179.5 (1)°, O3—-C8–C4—C3 − 173.0 (1)°, C6—C5—C4—C8 − 179.5 (1)° and C1—C2—O2—C7 179.5 (1)°. The orientations of the groups outside the aromatic ring deviate slightly from planarity with the aromatic ring. Two kinds of intermolecular hydrogen bonds exist in the crystal structure, O—H···O and C—H···O (Table 2), and these lead to parallel packing of the molecules (Fig. 2).

S2. Experimental

The title compound was crystallized from a solution of 0.1 g of acetovanillone in 5 ml water, heated to totally dissolve the material. When the solution was cooled to room temperature, colorless crystals formed.

S3. Refinement

The resulting transmission factors, therefore, include contributions from absorption, crystal decay, and detectable variations in beam intensity. Hydroxyl atom H1 was refined, while all other H atoms were placed in calculated positions.

Computing details

Data collection: D*TREK (Molecular Structure Corporation, 2001); cell refinement: D*TREK; data reduction: D*TREK; program(s) used to solve structure: SIR97 (Altomare et al.. 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1985-1992); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. The molecular structure of acetovanillone, with the atom-numbering scheme and ellipsoids at the 50% probability level. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. Packing diagram of acetovanillone, viewed down the b axis. O—H···O and C—H···O hydrogen bonds are shown as dotted lines.

(I)

Crystal data

C9H10O3	F(000) = 352.00
Mr = 166.18	Dx = 1.378 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 8.5144 (8) Å	Cell parameters from 4394 reflections
b = 8.778 (1) Å	θ = 2.3–27.9°
c = 10.712 (1) Å	µ = 0.10 mm^−1
β = 90.082 (5)°	T = 173 K
V = 800.7 (1) Å^3	Prism, colorless
Z = 4	0.50 × 0.30 × 0.10 mm

Data collection

Rigaku/ADSC CCD diffractometer	1860 independent reflections
Radiation source: X-ray tube	1334 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 11.76 pixels mm^-1	θmax = 27.9°, θmin = 2.3°
area detector scans	h = −10→11
Absorption correction: multi-scan (D*TREK; Molecular Structure Corporation, 2001)	k = −11→11
Tmin = 0.703, Tmax = 1.000	l = −14→14
6942 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2) + 0.00093|Fo|^2]
S = 1.20	(Δ/σ)max < 0.001
1748 reflections	Δρmax = 0.38 e Å^−3
113 parameters	Δρmin = −0.27 e Å^−3

Special details

Experimental. Data were collected in 0.50° oscillations with 35 s exposures. A sweep of data was done using ϕ oscillations from 0.0 to 190.0° at χ = −90°, and a second sweep was performed using ω oscillations between −17.0 and 23.0° at χ = −90.0°. The crystal-to-detector distance was 38.78 mm. The detector swing angle was −5.5°. The absorption correction is based on a three-dimensional analysis of symmetry-equivalent data and is performed along with batch scaling in a single step.

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

	x	y	z	Uiso*/Ueq
O1	0.5548 (1)	0.7565 (1)	0.7150 (1)	0.0243 (3)
O2	0.2791 (1)	0.7013 (1)	0.6024 (1)	0.0217 (3)
O3	0.4765 (1)	0.0450 (1)	0.6650 (1)	0.0283 (3)
C1	0.5121 (1)	0.6113 (1)	0.6894 (1)	0.0166 (3)
C2	0.3689 (1)	0.5762 (1)	0.6309 (1)	0.0156 (3)
C3	0.3294 (1)	0.4263 (1)	0.6076 (1)	0.0164 (3)
C4	0.4315 (2)	0.3084 (1)	0.6433 (1)	0.0167 (3)
C5	0.5725 (2)	0.3442 (2)	0.7013 (1)	0.0190 (3)
C6	0.6131 (2)	0.4944 (2)	0.7238 (1)	0.0191 (3)
C7	0.1320 (2)	0.6732 (2)	0.5417 (1)	0.0244 (4)
C8	0.3917 (2)	0.1456 (2)	0.6219 (1)	0.0194 (3)
C9	0.2490 (2)	0.1042 (2)	0.5479 (1)	0.0259 (4)
H1	0.491 (3)	0.820 (3)	0.691 (2)	0.072 (8)*
H3	0.2297	0.4021	0.5664	0.019*
H5	0.6440	0.2623	0.7268	0.022*
H6	0.7135	0.5183	0.7640	0.023*
H7A	0.1505	0.6215	0.4621	0.029*
HB	0.0784	0.7702	0.5266	0.029*
H7C	0.0664	0.6087	0.5952	0.029*
H9B	0.2518	0.1566	0.4671	0.031*
H9C	0.1548	0.1352	0.5937	0.031*
H9A	0.2468	−0.0062	0.5343	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0225 (5)	0.0146 (5)	0.0357 (6)	−0.0006 (4)	−0.0126 (4)	0.0014 (4)
O2	0.0165 (5)	0.0160 (5)	0.0326 (6)	0.0052 (4)	−0.0105 (4)	−0.0024 (4)
O3	0.0276 (5)	0.0162 (5)	0.0411 (7)	0.0032 (4)	−0.0088 (5)	0.0006 (4)
C1	0.0153 (6)	0.0167 (6)	0.0178 (6)	−0.0013 (5)	−0.0022 (5)	0.0011 (5)
C2	0.0140 (6)	0.0168 (6)	0.0162 (6)	0.0040 (5)	−0.0010 (5)	0.0007 (5)
C3	0.0138 (6)	0.0181 (7)	0.0172 (6)	−0.0002 (5)	−0.0021 (5)	−0.0009 (5)
C4	0.0164 (6)	0.0161 (6)	0.0174 (6)	0.0009 (5)	0.0000 (5)	0.0017 (5)
C5	0.0158 (7)	0.0181 (7)	0.0230 (7)	0.0018 (5)	−0.0028 (5)	0.0056 (5)
C6	0.0148 (6)	0.0201 (7)	0.0224 (7)	−0.0013 (5)	−0.0048 (5)	0.0045 (5)
C7	0.0179 (7)	0.0225 (7)	0.0327 (8)	0.0052 (6)	−0.0106 (6)	−0.0012 (6)
C8	0.0189 (7)	0.0181 (6)	0.0212 (7)	−0.0003 (5)	0.0011 (5)	0.0005 (5)
C9	0.0261 (7)	0.0215 (7)	0.0299 (8)	−0.0041 (6)	−0.0071 (6)	0.0003 (6)

Geometric parameters (Å, º)

O1—C1	1.353 (2)	C4—C8	1.486 (2)
O1—H1	0.82 (3)	C5—C6	1.385 (2)
O2—C2	1.372 (2)	C5—H5	0.98
O2—C7	1.431 (2)	C6—H6	0.98
O3—C8	1.230 (2)	C7—H7A	0.98
C1—C2	1.404 (2)	C7—HB	0.98
C1—C6	1.388 (2)	C7—H7C	0.98
C2—C3	1.381 (2)	C8—C9	1.495 (2)
C3—C4	1.404 (2)	C9—H9B	0.98
C3—H3	0.98	C9—H9C	0.98
C4—C5	1.387 (2)	C9—H9A	0.98
O1···O3^i	2.673 (1)	O2···C9^i	3.594 (2)
O1···C5^ii	3.385 (2)	O3···C7^v	3.464 (2)
O1···C9^iii	3.497 (2)	O3···C9^vi	3.520 (2)
O1···C6^ii	3.575 (2)	C1···C3^iii	3.474 (2)
O2···C8^iv	3.330 (2)	C1···C9^iv	3.590 (2)
O2···C4^iv	3.395 (2)	C2···C8^iv	3.511 (2)
O2···C5^iii	3.515 (2)	C2···C4^iii	3.543 (2)
O2···O3^i	3.518 (1)	C2···C9^iv	3.595 (2)
O2···O3^iv	3.583 (2)	C5···C7^v	3.588 (2)
C1—O1—H1	113 (2)	C1—C6—H6	119.9
C2—O2—C7	116.8 (1)	C5—C6—H6	119.9
O1—C1—C2	122.0 (1)	O2—C7—H7A	109.5
O1—C1—C6	118.4 (1)	O2—C7—HB	109.4
C2—C1—C6	119.6 (1)	O2—C7—H7C	109.4
O2—C2—C1	114.0 (1)	H7A—C7—HB	109.6
O2—C2—C3	125.9 (1)	H7A—C7—H7C	109.5
C1—C2—C3	120.0 (1)	HB—C7—H7C	109.4
C2—C3—C4	120.2 (1)	O3—C8—C4	119.9 (1)
C2—C3—H3	119.9	O3—C8—C9	120.1 (1)
C4—C3—H3	119.9	C4—C8—C9	120.1 (1)
C3—C4—C5	119.3 (1)	C8—C9—H9B	109.5
C3—C4—C8	121.7 (1)	C8—C9—H9C	109.4
C5—C4—C8	119.0 (1)	C8—C9—H9A	109.5
C4—C5—C6	120.6 (1)	H9B—C9—H9C	109.5
C4—C5—H5	119.7	H9B—C9—H9A	109.4
C6—C5—H5	119.7	H9C—C9—H9A	109.5
C1—C6—C5	120.2 (1)
O1—C1—C2—O2	0.3 (2)	C2—C1—C6—C5	−0.4 (2)
O1—C1—C2—C3	−179.3 (1)	C2—C3—C4—C5	−0.4 (2)
O1—C1—C6—C5	178.8 (1)	C2—C3—C4—C8	178.9 (1)
O2—C2—C1—C6	179.5 (1)	C3—C2—O2—C7	−0.9 (2)
O2—C2—C3—C4	−179.0 (1)	C3—C2—C1—C6	−0.1 (2)
O3—C8—C4—C3	−173.0 (1)	C3—C4—C5—C6	−0.2 (2)
O3—C8—C4—C5	6.4 (2)	C3—C4—C8—C9	7.1 (2)
C1—C2—O2—C7	179.5 (1)	C5—C4—C8—C9	−173.6 (1)
C1—C2—C3—C4	0.5 (2)	C6—C5—C4—C8	−179.5 (1)
C1—C6—C5—C4	0.6 (2)

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x+1/2, y−1/2, −z+3/2; (vi) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82 (2)	2.29 (3)	2.682 (1)	110 (2)
O1—H1···O3^i	0.82 (2)	2.00 (3)	2.673 (1)	139 (2)
C9—H9B···O1^iii	0.98	2.67	3.497 (2)	143

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