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

Kumar, S.; Chandra; Rajesh, B.M.; Mahendra, M.; Doreswamy, B.H.

doi:10.1107/S2414314617001833

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170183

https://doi.org/10.1107/S2414314617001833

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

Shamantha Kumar,^a Chandra,^b B. M. Rajesh,^c M. Mahendra ^b and B. H. Doreswamy ^a ^*

^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.

Keywords: crystal structure; benzoate derivative; hydrogen bonding.

CCDC reference: 1530685

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 ), the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the molecule (Fig. 1), 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) features C—H⋯O contacts (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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
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
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.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₅
M_r	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)
V (Å³)	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
R_int	0.055
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.37
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1530685

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001833/bt4035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001833/bt4035Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001833/bt4035Isup3.cml

checkCIF report

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

C₁₈H₁₈O₅	Z = 2
M_r = 314.32	F(000) = 332
Triclinic, P1	D_x = 1.364 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.9805 (3) Å	Cell parameters from 2522 reflections
b = 8.6087 (3) Å	θ = 5.2–64.5°
c = 11.4674 (4) Å	µ = 0.82 mm⁻¹
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 Anode	R_int = 0.055
Graphite monochromator	θ_max = 64.5°, θ_min = 5.2°
Detector resolution: 18.4 pixels mm^-1	h = −9→9
φ and ω scans	k = −10→9
10314 measured reflections	l = −13→13
2522 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.121P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2522 reflections	Δρ_max = 0.30 e Å⁻³
212 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: shelxl, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction 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

	x	y	z	U_iso*/U_eq
O9	−0.09184 (18)	0.75607 (14)	0.67623 (13)	0.0300 (5)
O11	0.19147 (17)	0.78179 (14)	0.83817 (13)	0.0261 (5)
O13	0.08365 (17)	0.82775 (14)	1.00977 (13)	0.0288 (5)
O20	0.42611 (16)	0.24229 (13)	0.82041 (12)	0.0234 (4)
O22	0.39935 (16)	0.15667 (14)	1.02101 (12)	0.0228 (4)
C1	−0.2712 (3)	1.3978 (3)	0.4619 (2)	0.0363 (7)
C2	−0.2107 (2)	1.2678 (2)	0.52842 (18)	0.0251 (6)
C3	−0.0852 (2)	1.2978 (2)	0.62938 (18)	0.0246 (6)
C4	−0.0257 (2)	1.1782 (2)	0.68962 (18)	0.0230 (6)
C5	−0.0911 (2)	1.0230 (2)	0.64858 (17)	0.0204 (6)
C6	−0.2189 (2)	0.9924 (2)	0.54882 (19)	0.0252 (6)
C7	−0.2772 (2)	1.1132 (2)	0.48971 (19)	0.0262 (6)
C8	−0.0261 (2)	0.8887 (2)	0.70705 (17)	0.0218 (6)
C10	0.1250 (2)	0.9248 (2)	0.80637 (19)	0.0246 (6)
C12	0.1576 (2)	0.7440 (2)	0.94225 (18)	0.0222 (6)
C14	0.2227 (2)	0.5891 (2)	0.96242 (18)	0.0210 (6)
C15	0.2037 (2)	0.5396 (2)	1.06763 (19)	0.0225 (6)
C16	0.2605 (2)	0.3952 (2)	1.09167 (18)	0.0211 (6)
C17	0.3360 (2)	0.29900 (19)	1.00736 (18)	0.0198 (6)
C18	0.3534 (2)	0.34750 (19)	0.89866 (18)	0.0189 (6)
C19	0.2971 (2)	0.4923 (2)	0.87634 (18)	0.0197 (6)
C21	0.4526 (3)	0.2905 (2)	0.71130 (18)	0.0257 (6)
C23	0.3883 (3)	0.1034 (2)	1.13133 (19)	0.0263 (6)
H3	−0.04010	1.40040	0.65730	0.0300*
H4	0.05780	1.20130	0.75740	0.0280*
H6	−0.26570	0.89020	0.52160	0.0300*
H7	−0.36240	1.09050	0.42290	0.0310*
H10A	0.21260	0.98460	0.78040	0.0300*
H10B	0.09130	0.98870	0.87600	0.0300*
H17	0.15210	0.60370	1.12370	0.0270*
H19	0.30870	0.52490	0.80460	0.0240*
H22	0.24800	0.36330	1.16350	0.0250*
H25A	0.44430	0.18050	1.19730	0.0390*
H25B	0.44210	0.00500	1.13200	0.0390*
H25C	0.27090	0.08890	1.13870	0.0390*
H28A	0.34490	0.30480	0.66470	0.0380*
H28B	0.51060	0.21090	0.66650	0.0380*
H28C	0.52010	0.38810	0.72930	0.0380*
H99A	−0.24360	1.49800	0.51370	0.0540*
H99B	−0.39200	1.38420	0.43670	0.0540*
H99C	−0.21640	1.39410	0.39290	0.0540*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O9	0.0366 (9)	0.0196 (7)	0.0341 (9)	−0.0002 (5)	0.0066 (7)	0.0049 (6)
O11	0.0334 (8)	0.0210 (7)	0.0272 (9)	0.0128 (5)	0.0084 (6)	0.0090 (6)
O13	0.0348 (8)	0.0227 (7)	0.0329 (9)	0.0118 (6)	0.0152 (7)	0.0055 (6)
O20	0.0313 (8)	0.0185 (7)	0.0220 (8)	0.0066 (5)	0.0096 (6)	0.0021 (5)
O22	0.0286 (8)	0.0167 (6)	0.0258 (8)	0.0085 (5)	0.0077 (6)	0.0069 (5)
C1	0.0465 (14)	0.0344 (11)	0.0317 (13)	0.0144 (9)	0.0075 (11)	0.0134 (9)
C2	0.0264 (11)	0.0285 (10)	0.0241 (12)	0.0107 (8)	0.0109 (9)	0.0077 (8)
C3	0.0286 (11)	0.0205 (9)	0.0265 (12)	0.0043 (7)	0.0080 (9)	0.0057 (8)
C4	0.0225 (10)	0.0242 (9)	0.0228 (11)	0.0036 (7)	0.0032 (8)	0.0059 (8)
C5	0.0220 (10)	0.0218 (10)	0.0194 (11)	0.0042 (7)	0.0090 (8)	0.0039 (7)
C6	0.0261 (10)	0.0243 (10)	0.0239 (12)	0.0017 (7)	0.0040 (9)	0.0010 (8)
C7	0.0269 (11)	0.0318 (10)	0.0190 (11)	0.0072 (8)	0.0028 (8)	0.0024 (8)
C8	0.0259 (10)	0.0197 (9)	0.0224 (11)	0.0051 (7)	0.0106 (9)	0.0040 (8)
C10	0.0282 (11)	0.0178 (9)	0.0296 (12)	0.0070 (7)	0.0047 (9)	0.0082 (8)
C12	0.0182 (10)	0.0204 (9)	0.0276 (12)	0.0013 (7)	0.0027 (9)	0.0040 (8)
C14	0.0165 (10)	0.0171 (9)	0.0287 (12)	0.0033 (7)	0.0029 (8)	0.0029 (8)
C15	0.0204 (10)	0.0195 (9)	0.0288 (12)	0.0052 (7)	0.0089 (9)	0.0027 (8)
C16	0.0208 (10)	0.0216 (9)	0.0214 (11)	0.0017 (7)	0.0041 (8)	0.0047 (8)
C17	0.0163 (9)	0.0161 (9)	0.0266 (12)	0.0019 (7)	0.0023 (8)	0.0039 (8)
C18	0.0175 (9)	0.0158 (9)	0.0226 (11)	0.0033 (7)	0.0045 (8)	−0.0007 (7)
C19	0.0179 (9)	0.0187 (9)	0.0225 (11)	0.0006 (7)	0.0026 (8)	0.0042 (8)
C21	0.0327 (11)	0.0246 (9)	0.0208 (11)	0.0038 (8)	0.0088 (9)	0.0027 (8)
C23	0.0346 (11)	0.0220 (9)	0.0257 (12)	0.0083 (8)	0.0085 (9)	0.0093 (8)

Geometric parameters (Å, º) top

O9—C8	1.216 (2)	C16—C17	1.388 (3)
O11—C10	1.433 (2)	C17—C18	1.405 (3)
O11—C12	1.354 (2)	C18—C19	1.386 (2)
O13—C12	1.203 (2)	C1—H99A	0.9600
O20—C18	1.372 (2)	C1—H99B	0.9600
O20—C21	1.427 (2)	C1—H99C	0.9600
O22—C17	1.361 (2)	C3—H3	0.9300
O22—C23	1.431 (2)	C4—H4	0.9300
C1—C2	1.505 (3)	C6—H6	0.9300
C2—C3	1.388 (3)	C7—H7	0.9300
C2—C7	1.393 (3)	C10—H10A	0.9700
C3—C4	1.387 (3)	C10—H10B	0.9700
C4—C5	1.398 (2)	C15—H17	0.9300
C5—C6	1.390 (3)	C16—H22	0.9300
C5—C8	1.496 (3)	C19—H19	0.9300
C6—C7	1.385 (3)	C21—H28A	0.9600
C8—C10	1.507 (3)	C21—H28B	0.9600
C12—C14	1.484 (2)	C21—H28C	0.9600
C14—C15	1.374 (3)	C23—H25A	0.9600
C14—C19	1.399 (3)	C23—H25B	0.9600
C15—C16	1.390 (2)	C23—H25C	0.9600

C10—O11—C12	116.65 (14)	H99A—C1—H99B	110.00
C18—O20—C21	116.91 (14)	H99A—C1—H99C	109.00
C17—O22—C23	117.24 (15)	H99B—C1—H99C	109.00
C1—C2—C3	121.05 (17)	C2—C3—H3	119.00
C1—C2—C7	121.07 (18)	C4—C3—H3	119.00
C3—C2—C7	117.87 (17)	C3—C4—H4	120.00
C2—C3—C4	121.50 (17)	C5—C4—H4	120.00
C3—C4—C5	120.11 (17)	C5—C6—H6	120.00
C4—C5—C6	118.75 (16)	C7—C6—H6	120.00
C4—C5—C8	122.23 (16)	C2—C7—H7	119.00
C6—C5—C8	119.01 (16)	C6—C7—H7	119.00
C5—C6—C7	120.44 (17)	O11—C10—H10A	110.00
C2—C7—C6	121.30 (18)	O11—C10—H10B	110.00
O9—C8—C5	121.72 (16)	C8—C10—H10A	110.00
O9—C8—C10	121.22 (16)	C8—C10—H10B	110.00
C5—C8—C10	117.06 (15)	H10A—C10—H10B	108.00
O11—C10—C8	110.52 (15)	C14—C15—H17	120.00
O11—C12—O13	123.23 (16)	C16—C15—H17	119.00
O11—C12—C14	112.10 (15)	C15—C16—H22	120.00
O13—C12—C14	124.67 (18)	C17—C16—H22	120.00
C12—C14—C15	118.14 (16)	C14—C19—H19	120.00
C12—C14—C19	121.80 (17)	C18—C19—H19	120.00
C15—C14—C19	120.04 (16)	O20—C21—H28A	109.00
C14—C15—C16	121.05 (17)	O20—C21—H28B	109.00
C15—C16—C17	119.34 (18)	O20—C21—H28C	109.00
O22—C17—C16	125.00 (17)	H28A—C21—H28B	109.00
O22—C17—C18	115.00 (16)	H28A—C21—H28C	109.00
C16—C17—C18	119.99 (16)	H28B—C21—H28C	110.00
O20—C18—C17	115.38 (15)	O22—C23—H25A	109.00
O20—C18—C19	124.65 (17)	O22—C23—H25B	109.00
C17—C18—C19	119.97 (17)	O22—C23—H25C	109.00
C14—C19—C18	119.59 (18)	H25A—C23—H25B	110.00
C2—C1—H99A	109.00	H25A—C23—H25C	109.00
C2—C1—H99B	109.00	H25B—C23—H25C	109.00
C2—C1—H99C	109.00

C12—O11—C10—C8	−105.06 (18)	C5—C6—C7—C2	−0.3 (3)
C10—O11—C12—O13	−3.9 (3)	O9—C8—C10—O11	10.7 (2)
C10—O11—C12—C14	176.33 (14)	C5—C8—C10—O11	−169.40 (15)
C21—O20—C18—C17	−177.34 (16)	O11—C12—C14—C15	177.09 (16)
C21—O20—C18—C19	3.3 (2)	O11—C12—C14—C19	−4.8 (2)
C23—O22—C17—C16	−0.6 (3)	O13—C12—C14—C15	−2.7 (3)
C23—O22—C17—C18	178.63 (16)	O13—C12—C14—C19	175.41 (17)
C1—C2—C3—C4	−178.44 (18)	C12—C14—C15—C16	179.44 (16)
C7—C2—C3—C4	0.7 (3)	C19—C14—C15—C16	1.3 (3)
C1—C2—C7—C6	178.34 (18)	C12—C14—C19—C18	−178.94 (16)
C3—C2—C7—C6	−0.8 (3)	C15—C14—C19—C18	−0.9 (3)
C2—C3—C4—C5	0.5 (3)	C14—C15—C16—C17	−0.7 (3)
C3—C4—C5—C6	−1.6 (3)	C15—C16—C17—O22	178.78 (16)
C3—C4—C5—C8	177.30 (16)	C15—C16—C17—C18	−0.4 (3)
C4—C5—C6—C7	1.5 (3)	O22—C17—C18—O20	2.2 (2)
C8—C5—C6—C7	−177.43 (16)	O22—C17—C18—C19	−178.44 (15)
C4—C5—C8—O9	174.62 (17)	C16—C17—C18—O20	−178.56 (15)
C4—C5—C8—C10	−5.3 (2)	C16—C17—C18—C19	0.8 (3)
C6—C5—C8—O9	−6.5 (3)	O20—C18—C19—C14	179.13 (16)
C6—C5—C8—C10	173.57 (16)	C17—C18—C19—C14	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O13	0.97	2.24	2.671 (2)	106
C10—H10B···O13ⁱ	0.97	2.48	3.399 (2)	157
C19—H19···O11	0.93	2.42	2.733 (2)	100
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.

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

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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