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

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ISSN: 2414-3146

2-(4-Methyl­phen­yl)-2-oxo­ethyl 3,4-di­meth­­oxy­benzoate

aDepartment of Physics, SJB Institute of Technology, Kengeri, Bangalore 560 060, India, bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and cDepartment of Physics, R V College of Engineering, Bangalore 560 059, India
*Correspondence e-mail: mychandru.10@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 27 December 2016; accepted 2 February 2017; online 14 February 2017)

In the title compound, C18H18O5, the dihedral angle between the mean planes of the two aromatic rings is 66.55 (8)°. The crystal packing features by inter­molecular C—H⋯O contacts.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Benzoate and its derivatives are well known heterocyclic compounds, which have a variety of biological activities. As a part of our ongoing research on benzoate derivatives (Kumar et al., 2016[Kumar, S., Chandra, Dileep, C. S., Mahendra, M. & Doreswamy, B. H. (2016). IUCrData, 1, x160867.]), the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the mol­ecule (Fig. 1[link]), the dihedral angle between the mean planes of the benzoate (C14–C19) and phenyl groups (C2–C7) is 66.55 (8)°. The crystal packing (Fig. 2[link]) features C—H⋯O contacts (Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10B⋯O13i 0.97 2.48 3.399 (2) 157
C23—H25B⋯O20ii 0.96 2.50 3.447 (2) 168
C23—H25B⋯O22ii 0.96 2.57 3.281 (2) 131
Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x+1, -y, -z+2.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles of arbitrary radius.
[Figure 2]
Figure 2
The crystal packing.

Synthesis and crystallization

Potassium carbonate was added to the solution of 3,4-di­meth­oxy­benzoic acid (1) in water and the mixture was stirred for 30 min. Then, a solution of 2-bromo-1-(p-tol­yl)ethanone (2) in ethanol was added and the reaction mixture was heated under reflux for 6 h. After completion of the reaction, ethanol was removed under reduced pressure. The obtained crystals were collected by filtration and recrystallized using ethanol.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C18H18O5
Mr 314.32
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 7.9805 (3), 8.6087 (3), 11.4674 (4)
α, β, γ (°) 99.678 (2), 99.173 (2), 91.495 (2)
V3) 765.55 (5)
Z 2
Radiation type Cu Kα
μ (mm−1) 0.82
Crystal size (mm) 0.30 × 0.25 × 0.20
 
Data collection
Diffractometer Bruker X8 Proteum
No. of measured, independent and observed [I > 2σ(I)] reflections 10314, 2522, 2053
Rint 0.055
(sin θ/λ)max−1) 0.585
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.169, 1.06
No. of reflections 2522
No. of parameters 212
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.30, −0.37
Computer programs: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

2-(4-Methylphenyl)-2-oxoethyl 3,4-dimethoxybenzoate top
Crystal data top
C18H18O5Z = 2
Mr = 314.32F(000) = 332
Triclinic, P1Dx = 1.364 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 7.9805 (3) ÅCell parameters from 2522 reflections
b = 8.6087 (3) Åθ = 5.2–64.5°
c = 11.4674 (4) ŵ = 0.82 mm1
α = 99.678 (2)°T = 293 K
β = 99.173 (2)°Block, light yellow
γ = 91.495 (2)°0.30 × 0.25 × 0.20 mm
V = 765.55 (5) Å3
Data collection top
Bruker X8 Proteum
diffractometer
2053 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.055
Graphite monochromatorθmax = 64.5°, θmin = 5.2°
Detector resolution: 18.4 pixels mm-1h = 99
φ and ω scansk = 109
10314 measured reflectionsl = 1313
2522 independent reflections
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.121P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2522 reflectionsΔρmax = 0.30 e Å3
212 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: shelxl, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (2)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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 (Å2) top
xyzUiso*/Ueq
O90.09184 (18)0.75607 (14)0.67623 (13)0.0300 (5)
O110.19147 (17)0.78179 (14)0.83817 (13)0.0261 (5)
O130.08365 (17)0.82775 (14)1.00977 (13)0.0288 (5)
O200.42611 (16)0.24229 (13)0.82041 (12)0.0234 (4)
O220.39935 (16)0.15667 (14)1.02101 (12)0.0228 (4)
C10.2712 (3)1.3978 (3)0.4619 (2)0.0363 (7)
C20.2107 (2)1.2678 (2)0.52842 (18)0.0251 (6)
C30.0852 (2)1.2978 (2)0.62938 (18)0.0246 (6)
C40.0257 (2)1.1782 (2)0.68962 (18)0.0230 (6)
C50.0911 (2)1.0230 (2)0.64858 (17)0.0204 (6)
C60.2189 (2)0.9924 (2)0.54882 (19)0.0252 (6)
C70.2772 (2)1.1132 (2)0.48971 (19)0.0262 (6)
C80.0261 (2)0.8887 (2)0.70705 (17)0.0218 (6)
C100.1250 (2)0.9248 (2)0.80637 (19)0.0246 (6)
C120.1576 (2)0.7440 (2)0.94225 (18)0.0222 (6)
C140.2227 (2)0.5891 (2)0.96242 (18)0.0210 (6)
C150.2037 (2)0.5396 (2)1.06763 (19)0.0225 (6)
C160.2605 (2)0.3952 (2)1.09167 (18)0.0211 (6)
C170.3360 (2)0.29900 (19)1.00736 (18)0.0198 (6)
C180.3534 (2)0.34750 (19)0.89866 (18)0.0189 (6)
C190.2971 (2)0.4923 (2)0.87634 (18)0.0197 (6)
C210.4526 (3)0.2905 (2)0.71130 (18)0.0257 (6)
C230.3883 (3)0.1034 (2)1.13133 (19)0.0263 (6)
H30.040101.400400.657300.0300*
H40.057801.201300.757400.0280*
H60.265700.890200.521600.0300*
H70.362401.090500.422900.0310*
H10A0.212600.984600.780400.0300*
H10B0.091300.988700.876000.0300*
H170.152100.603701.123700.0270*
H190.308700.524900.804600.0240*
H220.248000.363301.163500.0250*
H25A0.444300.180501.197300.0390*
H25B0.442100.005001.132000.0390*
H25C0.270900.088901.138700.0390*
H28A0.344900.304800.664700.0380*
H28B0.510600.210900.666500.0380*
H28C0.520100.388100.729300.0380*
H99A0.243601.498000.513700.0540*
H99B0.392001.384200.436700.0540*
H99C0.216401.394100.392900.0540*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O90.0366 (9)0.0196 (7)0.0341 (9)0.0002 (5)0.0066 (7)0.0049 (6)
O110.0334 (8)0.0210 (7)0.0272 (9)0.0128 (5)0.0084 (6)0.0090 (6)
O130.0348 (8)0.0227 (7)0.0329 (9)0.0118 (6)0.0152 (7)0.0055 (6)
O200.0313 (8)0.0185 (7)0.0220 (8)0.0066 (5)0.0096 (6)0.0021 (5)
O220.0286 (8)0.0167 (6)0.0258 (8)0.0085 (5)0.0077 (6)0.0069 (5)
C10.0465 (14)0.0344 (11)0.0317 (13)0.0144 (9)0.0075 (11)0.0134 (9)
C20.0264 (11)0.0285 (10)0.0241 (12)0.0107 (8)0.0109 (9)0.0077 (8)
C30.0286 (11)0.0205 (9)0.0265 (12)0.0043 (7)0.0080 (9)0.0057 (8)
C40.0225 (10)0.0242 (9)0.0228 (11)0.0036 (7)0.0032 (8)0.0059 (8)
C50.0220 (10)0.0218 (10)0.0194 (11)0.0042 (7)0.0090 (8)0.0039 (7)
C60.0261 (10)0.0243 (10)0.0239 (12)0.0017 (7)0.0040 (9)0.0010 (8)
C70.0269 (11)0.0318 (10)0.0190 (11)0.0072 (8)0.0028 (8)0.0024 (8)
C80.0259 (10)0.0197 (9)0.0224 (11)0.0051 (7)0.0106 (9)0.0040 (8)
C100.0282 (11)0.0178 (9)0.0296 (12)0.0070 (7)0.0047 (9)0.0082 (8)
C120.0182 (10)0.0204 (9)0.0276 (12)0.0013 (7)0.0027 (9)0.0040 (8)
C140.0165 (10)0.0171 (9)0.0287 (12)0.0033 (7)0.0029 (8)0.0029 (8)
C150.0204 (10)0.0195 (9)0.0288 (12)0.0052 (7)0.0089 (9)0.0027 (8)
C160.0208 (10)0.0216 (9)0.0214 (11)0.0017 (7)0.0041 (8)0.0047 (8)
C170.0163 (9)0.0161 (9)0.0266 (12)0.0019 (7)0.0023 (8)0.0039 (8)
C180.0175 (9)0.0158 (9)0.0226 (11)0.0033 (7)0.0045 (8)0.0007 (7)
C190.0179 (9)0.0187 (9)0.0225 (11)0.0006 (7)0.0026 (8)0.0042 (8)
C210.0327 (11)0.0246 (9)0.0208 (11)0.0038 (8)0.0088 (9)0.0027 (8)
C230.0346 (11)0.0220 (9)0.0257 (12)0.0083 (8)0.0085 (9)0.0093 (8)
Geometric parameters (Å, º) top
O9—C81.216 (2)C16—C171.388 (3)
O11—C101.433 (2)C17—C181.405 (3)
O11—C121.354 (2)C18—C191.386 (2)
O13—C121.203 (2)C1—H99A0.9600
O20—C181.372 (2)C1—H99B0.9600
O20—C211.427 (2)C1—H99C0.9600
O22—C171.361 (2)C3—H30.9300
O22—C231.431 (2)C4—H40.9300
C1—C21.505 (3)C6—H60.9300
C2—C31.388 (3)C7—H70.9300
C2—C71.393 (3)C10—H10A0.9700
C3—C41.387 (3)C10—H10B0.9700
C4—C51.398 (2)C15—H170.9300
C5—C61.390 (3)C16—H220.9300
C5—C81.496 (3)C19—H190.9300
C6—C71.385 (3)C21—H28A0.9600
C8—C101.507 (3)C21—H28B0.9600
C12—C141.484 (2)C21—H28C0.9600
C14—C151.374 (3)C23—H25A0.9600
C14—C191.399 (3)C23—H25B0.9600
C15—C161.390 (2)C23—H25C0.9600
C10—O11—C12116.65 (14)H99A—C1—H99B110.00
C18—O20—C21116.91 (14)H99A—C1—H99C109.00
C17—O22—C23117.24 (15)H99B—C1—H99C109.00
C1—C2—C3121.05 (17)C2—C3—H3119.00
C1—C2—C7121.07 (18)C4—C3—H3119.00
C3—C2—C7117.87 (17)C3—C4—H4120.00
C2—C3—C4121.50 (17)C5—C4—H4120.00
C3—C4—C5120.11 (17)C5—C6—H6120.00
C4—C5—C6118.75 (16)C7—C6—H6120.00
C4—C5—C8122.23 (16)C2—C7—H7119.00
C6—C5—C8119.01 (16)C6—C7—H7119.00
C5—C6—C7120.44 (17)O11—C10—H10A110.00
C2—C7—C6121.30 (18)O11—C10—H10B110.00
O9—C8—C5121.72 (16)C8—C10—H10A110.00
O9—C8—C10121.22 (16)C8—C10—H10B110.00
C5—C8—C10117.06 (15)H10A—C10—H10B108.00
O11—C10—C8110.52 (15)C14—C15—H17120.00
O11—C12—O13123.23 (16)C16—C15—H17119.00
O11—C12—C14112.10 (15)C15—C16—H22120.00
O13—C12—C14124.67 (18)C17—C16—H22120.00
C12—C14—C15118.14 (16)C14—C19—H19120.00
C12—C14—C19121.80 (17)C18—C19—H19120.00
C15—C14—C19120.04 (16)O20—C21—H28A109.00
C14—C15—C16121.05 (17)O20—C21—H28B109.00
C15—C16—C17119.34 (18)O20—C21—H28C109.00
O22—C17—C16125.00 (17)H28A—C21—H28B109.00
O22—C17—C18115.00 (16)H28A—C21—H28C109.00
C16—C17—C18119.99 (16)H28B—C21—H28C110.00
O20—C18—C17115.38 (15)O22—C23—H25A109.00
O20—C18—C19124.65 (17)O22—C23—H25B109.00
C17—C18—C19119.97 (17)O22—C23—H25C109.00
C14—C19—C18119.59 (18)H25A—C23—H25B110.00
C2—C1—H99A109.00H25A—C23—H25C109.00
C2—C1—H99B109.00H25B—C23—H25C109.00
C2—C1—H99C109.00
C12—O11—C10—C8105.06 (18)C5—C6—C7—C20.3 (3)
C10—O11—C12—O133.9 (3)O9—C8—C10—O1110.7 (2)
C10—O11—C12—C14176.33 (14)C5—C8—C10—O11169.40 (15)
C21—O20—C18—C17177.34 (16)O11—C12—C14—C15177.09 (16)
C21—O20—C18—C193.3 (2)O11—C12—C14—C194.8 (2)
C23—O22—C17—C160.6 (3)O13—C12—C14—C152.7 (3)
C23—O22—C17—C18178.63 (16)O13—C12—C14—C19175.41 (17)
C1—C2—C3—C4178.44 (18)C12—C14—C15—C16179.44 (16)
C7—C2—C3—C40.7 (3)C19—C14—C15—C161.3 (3)
C1—C2—C7—C6178.34 (18)C12—C14—C19—C18178.94 (16)
C3—C2—C7—C60.8 (3)C15—C14—C19—C180.9 (3)
C2—C3—C4—C50.5 (3)C14—C15—C16—C170.7 (3)
C3—C4—C5—C61.6 (3)C15—C16—C17—O22178.78 (16)
C3—C4—C5—C8177.30 (16)C15—C16—C17—C180.4 (3)
C4—C5—C6—C71.5 (3)O22—C17—C18—O202.2 (2)
C8—C5—C6—C7177.43 (16)O22—C17—C18—C19178.44 (15)
C4—C5—C8—O9174.62 (17)C16—C17—C18—O20178.56 (15)
C4—C5—C8—C105.3 (2)C16—C17—C18—C190.8 (3)
C6—C5—C8—O96.5 (3)O20—C18—C19—C14179.13 (16)
C6—C5—C8—C10173.57 (16)C17—C18—C19—C140.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O130.972.242.671 (2)106
C10—H10B···O13i0.972.483.399 (2)157
C19—H19···O110.932.422.733 (2)100
C23—H25B···O20ii0.962.503.447 (2)168
C23—H25B···O22ii0.962.573.281 (2)131
Symmetry codes: (i) x, y+2, z+2; (ii) x+1, y, z+2.
 

Acknowledgements

The authors would like to thank the SJB Institute of Technology, Kengeri, Bangalore, for their support. MM would like to thank UGC, New Delhi, Government of India, for awarding project F.41–920/2012(SR).

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKumar, S., Chandra, Dileep, C. S., Mahendra, M. & Doreswamy, B. H. (2016). IUCrData, 1, x160867.  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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