organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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(Acet­oxy)(2-methylphenyl)methyl acetate

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601204, India, bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: crystallography2010@gmail.com, phdguna@gmail.com

(Received 3 July 2011; accepted 16 July 2011; online 23 July 2011)

In the title compound, C12H14O4, the two acet­oxy groups are inclined by 57.92 (5)° and 62.71 (6)° to the benzene ring. An inter­molecular C—H⋯O inter­action involving the two acet­oxy groups generates a centrosymmetric dimer via an R22(16) ring motif.

Related literature

For the structure of the 4-methyl isomer, see: Rajnikant et al. (2009[Rajnikant, Sarmal, L., Dinesh, K. & Deshmukh, M. B. (2009). J. Chem. Crystallogr. 39, 835-837.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.])

[Scheme 1]

Experimental

Crystal data
  • C12H14O4

  • Mr = 222.23

  • Monoclinic, C 2/c

  • a = 15.757 (5) Å

  • b = 7.564 (5) Å

  • c = 19.886 (5) Å

  • β = 99.17 (5)°

  • V = 2339.8 (18) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 295 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.950, Tmax = 0.975

  • 12571 measured reflections

  • 2414 independent reflections

  • 1856 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.125

  • S = 1.05

  • 2414 reflections

  • 149 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C9—H9A⋯O4i 0.96 2.50 3.425 (3) 161
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The geometric parameters of the title molecule (Fig. 1) agree well with similar structure (Rajnikant et al., 2009). Intermolecular C—H···O interaction involving the two acetoxy groups generates a centrosymmetric dimer via R22(16) ring motif, Fig. 2 (Bernstein et al., 1995).

Related literature top

For the structure of 4-methyl isomer, see: Rajnikant et al. (2009). For graph-set notation, see: Bernstein et al. (1995)

Experimental top

To a solution of 2-methylbenzaldehyde (5 g, 41.61 mmol) in dry acetic anhydride (25 ml) anhydrous indium bromide (0.147 g, 0.416 mmol) was added. It was then stirred at room temperature for 4 h under nitrogen atmosphere. The reaction mixture was then poured over crushed ice (300 g). The solid obtained was filtered and washed thoroughly with water and the product was recrystallized from methanol to give pure product as a colorless solid with a yield of 82% and melting point 333 K.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for methine C—H, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl group.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The R22(16) ring set motif of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines (hydrogen atoms have been omitted).
(Acetoxy)(2-methylphenyl)methyl acetate top
Crystal data top
C12H14O4F(000) = 944
Mr = 222.23Dx = 1.262 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7598 reflections
a = 15.757 (5) Åθ = 2.1–26.5°
b = 7.564 (5) ŵ = 0.10 mm1
c = 19.886 (5) ÅT = 295 K
β = 99.17 (5)°Block, colourless
V = 2339.8 (18) Å30.25 × 0.20 × 0.15 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2414 independent reflections
Radiation source: fine-focus sealed tube1856 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scansθmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1319
Tmin = 0.950, Tmax = 0.975k = 98
12571 measured reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0609P)2 + 0.9232P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2414 reflectionsΔρmax = 0.20 e Å3
149 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0066 (8)
Crystal data top
C12H14O4V = 2339.8 (18) Å3
Mr = 222.23Z = 8
Monoclinic, C2/cMo Kα radiation
a = 15.757 (5) ŵ = 0.10 mm1
b = 7.564 (5) ÅT = 295 K
c = 19.886 (5) Å0.25 × 0.20 × 0.15 mm
β = 99.17 (5)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2414 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1856 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.975Rint = 0.027
12571 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.05Δρmax = 0.20 e Å3
2414 reflectionsΔρmin = 0.19 e Å3
149 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.70247 (11)0.0332 (2)0.68559 (8)0.0539 (4)
C20.77083 (15)0.0812 (3)0.73557 (9)0.0703 (6)
H20.75920.13540.77510.084*
C30.85476 (14)0.0510 (3)0.72841 (10)0.0744 (6)
H30.89900.08420.76280.089*
C40.87350 (12)0.0281 (3)0.67050 (10)0.0670 (5)
H40.93030.04920.66540.080*
C50.80723 (10)0.0760 (2)0.61999 (9)0.0530 (4)
H50.81960.12950.58060.064*
C60.72234 (10)0.04578 (19)0.62698 (7)0.0447 (4)
C70.65391 (10)0.10316 (19)0.56986 (7)0.0434 (4)
H70.59630.07830.58020.052*
C80.60492 (10)0.3993 (2)0.57295 (8)0.0513 (4)
C90.61840 (14)0.5811 (2)0.54922 (12)0.0794 (6)
H9A0.56460.64350.54240.119*
H9B0.64070.57620.50710.119*
H9C0.65860.64160.58280.119*
C100.60738 (10)0.0292 (2)0.45432 (8)0.0494 (4)
C110.62941 (13)0.0747 (3)0.39646 (10)0.0717 (5)
H11A0.57770.10680.36660.108*
H11B0.65980.17980.41330.108*
H11C0.66510.00500.37190.108*
C120.61143 (13)0.0643 (3)0.69723 (10)0.0740 (6)
H12A0.61190.13310.73790.111*
H12B0.58040.12690.65910.111*
H12C0.58400.04720.70220.111*
O10.66431 (6)0.28750 (13)0.55632 (5)0.0477 (3)
O20.54980 (9)0.35382 (19)0.60388 (8)0.0794 (4)
O30.66880 (7)0.01209 (13)0.51011 (5)0.0469 (3)
O40.54496 (8)0.11891 (18)0.45344 (6)0.0649 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0757 (11)0.0441 (9)0.0415 (9)0.0013 (8)0.0083 (8)0.0000 (7)
C20.1023 (16)0.0611 (11)0.0444 (10)0.0105 (11)0.0019 (9)0.0072 (8)
C30.0860 (14)0.0725 (13)0.0567 (12)0.0227 (11)0.0132 (10)0.0030 (10)
C40.0614 (10)0.0700 (12)0.0659 (12)0.0116 (9)0.0017 (9)0.0120 (10)
C50.0596 (10)0.0499 (9)0.0496 (9)0.0049 (7)0.0089 (7)0.0031 (7)
C60.0590 (9)0.0351 (7)0.0394 (8)0.0033 (6)0.0060 (6)0.0028 (6)
C70.0533 (8)0.0358 (8)0.0423 (8)0.0010 (6)0.0119 (6)0.0014 (6)
C80.0531 (9)0.0507 (9)0.0482 (9)0.0113 (7)0.0023 (7)0.0071 (7)
C90.0886 (14)0.0432 (10)0.1066 (17)0.0173 (10)0.0163 (12)0.0014 (10)
C100.0558 (9)0.0470 (9)0.0445 (9)0.0060 (7)0.0055 (7)0.0033 (7)
C110.0824 (13)0.0797 (13)0.0508 (10)0.0020 (10)0.0039 (9)0.0145 (9)
C120.0912 (14)0.0805 (13)0.0538 (11)0.0122 (11)0.0222 (10)0.0127 (10)
O10.0520 (6)0.0355 (6)0.0573 (7)0.0054 (4)0.0135 (5)0.0036 (5)
O20.0832 (9)0.0732 (9)0.0908 (10)0.0161 (7)0.0418 (8)0.0052 (8)
O30.0573 (6)0.0417 (6)0.0407 (6)0.0042 (4)0.0053 (5)0.0033 (4)
O40.0595 (7)0.0741 (9)0.0586 (7)0.0104 (6)0.0021 (6)0.0037 (6)
Geometric parameters (Å, º) top
C1—C61.389 (2)C8—O21.192 (2)
C1—C21.392 (3)C8—O11.3413 (19)
C1—C121.508 (3)C8—C91.480 (3)
C2—C31.372 (3)C9—H9A0.9600
C2—H20.9300C9—H9B0.9600
C3—C41.371 (3)C9—H9C0.9600
C3—H30.9300C10—O41.1929 (19)
C4—C51.377 (2)C10—O31.3572 (19)
C4—H40.9300C10—C111.480 (3)
C5—C61.386 (2)C11—H11A0.9600
C5—H50.9300C11—H11B0.9600
C6—C71.500 (2)C11—H11C0.9600
C7—O31.4248 (18)C12—H12A0.9600
C7—O11.434 (2)C12—H12B0.9600
C7—H70.9800C12—H12C0.9600
C6—C1—C2117.32 (17)O2—C8—C9125.89 (16)
C6—C1—C12122.91 (15)O1—C8—C9111.48 (16)
C2—C1—C12119.76 (17)C8—C9—H9A109.5
C3—C2—C1122.11 (18)C8—C9—H9B109.5
C3—C2—H2118.9H9A—C9—H9B109.5
C1—C2—H2118.9C8—C9—H9C109.5
C4—C3—C2120.01 (17)H9A—C9—H9C109.5
C4—C3—H3120.0H9B—C9—H9C109.5
C2—C3—H3120.0O4—C10—O3123.03 (15)
C3—C4—C5119.19 (19)O4—C10—C11125.86 (16)
C3—C4—H4120.4O3—C10—C11111.10 (15)
C5—C4—H4120.4C10—C11—H11A109.5
C4—C5—C6121.02 (17)C10—C11—H11B109.5
C4—C5—H5119.5H11A—C11—H11B109.5
C6—C5—H5119.5C10—C11—H11C109.5
C5—C6—C1120.36 (15)H11A—C11—H11C109.5
C5—C6—C7117.72 (14)H11B—C11—H11C109.5
C1—C6—C7121.92 (14)C1—C12—H12A109.5
O3—C7—O1105.94 (11)C1—C12—H12B109.5
O3—C7—C6107.31 (12)H12A—C12—H12B109.5
O1—C7—C6109.49 (12)C1—C12—H12C109.5
O3—C7—H7111.3H12A—C12—H12C109.5
O1—C7—H7111.3H12B—C12—H12C109.5
C6—C7—H7111.3C8—O1—C7117.51 (13)
O2—C8—O1122.63 (16)C10—O3—C7116.42 (12)
C6—C1—C2—C30.7 (3)C1—C6—C7—O3121.51 (15)
C12—C1—C2—C3178.03 (19)C5—C6—C7—O155.29 (17)
C1—C2—C3—C40.3 (3)C1—C6—C7—O1123.95 (15)
C2—C3—C4—C50.1 (3)O2—C8—O1—C77.3 (2)
C3—C4—C5—C60.1 (3)C9—C8—O1—C7173.66 (14)
C4—C5—C6—C10.3 (2)O3—C7—O1—C8134.50 (12)
C4—C5—C6—C7179.53 (15)C6—C7—O1—C8110.08 (14)
C2—C1—C6—C50.7 (2)O4—C10—O3—C72.1 (2)
C12—C1—C6—C5177.99 (17)C11—C10—O3—C7178.64 (14)
C2—C1—C6—C7179.89 (15)O1—C7—O3—C1071.00 (15)
C12—C1—C6—C71.2 (2)C6—C7—O3—C10172.10 (12)
C5—C6—C7—O359.25 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O4i0.962.503.425 (3)161
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC12H14O4
Mr222.23
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)15.757 (5), 7.564 (5), 19.886 (5)
β (°) 99.17 (5)
V3)2339.8 (18)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.950, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
12571, 2414, 1856
Rint0.027
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.125, 1.05
No. of reflections2414
No. of parameters149
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O4i0.962.503.425 (3)161
Symmetry code: (i) x+1, y+1, z+1.
 

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationRajnikant, Sarmal, L., Dinesh, K. & Deshmukh, M. B. (2009). J. Chem. Crystallogr. 39, 835–837.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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