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ISSN: 2056-9890

2-Meth­­oxy-4-(prop-2-en-1-yl)phenyl benzoate

aDepartment of Pharmaceutical Chemistry, International Medical University, 126 Jalan Bukit Jalil, 57000 Kuala Lumpur, Malaysia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: mallikarjunarao_pichika@imu.edu.my

(Received 3 June 2013; accepted 6 June 2013; online 12 June 2013)

In the title compound, C17H16O3, the benzene rings are twisted by 63.54 (5)°. The twist is similar to that found in the unsubstituted compound, phenyl benzoate. The crystal packing features C—H⋯O hydrogen bonds.

Related literature

For the structure of phenyl benzoate, see: Shibakami & Sekiya (1995[Shibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326-330.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16O3

  • Mr = 268.30

  • Monoclinic, P 21 /c

  • a = 9.9334 (6) Å

  • b = 9.5124 (5) Å

  • c = 14.9463 (9) Å

  • β = 103.405 (6)°

  • V = 1373.81 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.966, Tmax = 0.983

  • 7024 measured reflections

  • 3168 independent reflections

  • 2242 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.138

  • S = 1.05

  • 3168 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O3i 0.95 2.55 3.256 (2) 131
C15—H15⋯O3ii 0.95 2.54 3.209 (2) 128
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The title phenyl benzoate (Scheme I, Fig. 1), which possesses an allyl and a methoxy substituent, was synthesized for an evaluation of its pharmaceutical properties as it is an ester derivative of eugenol. The two benzene rings are approximately perpendicular [dihedral angle 63.54 (5)°]. The twist is similar to that found in the unsubstituted compound, phenyl benzoate (Shibakami & Sekiya, 1995).

Related literature top

For the structure of phenyl benzoate, see: Shibakami & Sekiya (1995).

Experimental top

4-Allyl-2-methoxyphenol (1 mmol), benzoic acid (1 mmol), diethylazodicarboxylate (2 mmol) and triphenylphosphine (2 mmol) were heated in THF (10 ml) for 2 h. The solid material extracted with dichloromethane. The dichloromethane solution was eluted through a silica gel column by using an n-hexane–ethyl acetate (95: 5 v/v) solvent system. Slow evaporation of the solution yielded large colorless crystals.

Refinement top

H-atoms were placed in calculated positions [C–H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C17H16O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
2-Methoxy-4-(prop-2-en-1-yl)phenyl benzoate top
Crystal data top
C17H16O3F(000) = 568
Mr = 268.30Dx = 1.297 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1957 reflections
a = 9.9334 (6) Åθ = 3.0–27.5°
b = 9.5124 (5) ŵ = 0.09 mm1
c = 14.9463 (9) ÅT = 100 K
β = 103.405 (6)°Prism, colorless
V = 1373.81 (14) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
3168 independent reflections
Radiation source: SuperNova (Mo) X-ray Source2242 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.041
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 3.0°
ω scanh = 1012
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 912
Tmin = 0.966, Tmax = 0.983l = 1916
7024 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0572P)2 + 0.1625P]
where P = (Fo2 + 2Fc2)/3
3168 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C17H16O3V = 1373.81 (14) Å3
Mr = 268.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.9334 (6) ŵ = 0.09 mm1
b = 9.5124 (5) ÅT = 100 K
c = 14.9463 (9) Å0.40 × 0.30 × 0.20 mm
β = 103.405 (6)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
3168 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
2242 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.983Rint = 0.041
7024 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.05Δρmax = 0.23 e Å3
3168 reflectionsΔρmin = 0.29 e Å3
181 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.40190 (12)0.28310 (12)0.60263 (8)0.0266 (3)
O20.22747 (12)0.48286 (12)0.63406 (8)0.0241 (3)
O30.09998 (13)0.28409 (12)0.60909 (8)0.0266 (3)
C10.25534 (17)0.47175 (17)0.54614 (11)0.0216 (4)
C20.19517 (17)0.56488 (17)0.47895 (12)0.0232 (4)
H20.13020.63190.49040.028*
C30.22950 (17)0.56121 (18)0.39346 (12)0.0236 (4)
H30.18770.62570.34670.028*
C40.32409 (17)0.46399 (17)0.37666 (11)0.0216 (4)
C50.38323 (17)0.36863 (17)0.44573 (11)0.0220 (4)
H50.44720.30070.43410.026*
C60.35012 (17)0.37154 (17)0.53098 (11)0.0218 (4)
C70.48978 (19)0.1729 (2)0.58544 (13)0.0305 (4)
H7A0.52150.11710.64150.046*
H7B0.56990.21330.56690.046*
H7C0.43840.11240.53610.046*
C80.36682 (18)0.45729 (18)0.28547 (11)0.0241 (4)
H8A0.46470.48700.29570.029*
H8B0.36130.35830.26450.029*
C90.2825 (2)0.5455 (2)0.21071 (12)0.0300 (4)
H90.18770.52140.18880.036*
C100.3292 (3)0.6537 (2)0.17302 (14)0.0429 (5)
H10A0.42340.68090.19310.052*
H10B0.26900.70490.12550.052*
C110.15078 (17)0.37820 (17)0.65969 (12)0.0215 (4)
C120.13802 (17)0.39478 (17)0.75630 (11)0.0206 (4)
C130.08089 (17)0.28421 (18)0.79540 (12)0.0233 (4)
H130.04930.20260.76010.028*
C140.06989 (18)0.29291 (19)0.88614 (12)0.0264 (4)
H140.03240.21640.91330.032*
C150.11346 (18)0.41292 (18)0.93709 (12)0.0261 (4)
H150.10640.41850.99930.031*
C160.16721 (18)0.52473 (18)0.89742 (12)0.0262 (4)
H160.19470.60790.93200.031*
C170.18109 (18)0.51586 (18)0.80734 (12)0.0233 (4)
H170.21980.59200.78060.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0297 (7)0.0284 (7)0.0225 (6)0.0055 (6)0.0076 (5)0.0056 (5)
O20.0305 (7)0.0244 (6)0.0196 (6)0.0024 (5)0.0102 (5)0.0015 (5)
O30.0295 (7)0.0267 (7)0.0244 (7)0.0031 (6)0.0082 (5)0.0049 (5)
C10.0244 (9)0.0236 (9)0.0183 (8)0.0042 (7)0.0078 (7)0.0027 (7)
C20.0261 (9)0.0196 (8)0.0255 (9)0.0013 (7)0.0089 (7)0.0018 (7)
C30.0268 (9)0.0228 (8)0.0210 (9)0.0002 (8)0.0048 (7)0.0019 (7)
C40.0247 (9)0.0211 (8)0.0193 (8)0.0039 (7)0.0054 (7)0.0022 (7)
C50.0208 (9)0.0215 (8)0.0251 (9)0.0002 (7)0.0079 (7)0.0000 (7)
C60.0219 (8)0.0215 (8)0.0212 (8)0.0028 (7)0.0032 (7)0.0027 (7)
C70.0315 (10)0.0299 (10)0.0310 (10)0.0054 (9)0.0094 (8)0.0073 (8)
C80.0283 (9)0.0243 (9)0.0210 (9)0.0010 (8)0.0081 (7)0.0000 (7)
C90.0360 (10)0.0338 (10)0.0212 (9)0.0042 (9)0.0087 (8)0.0002 (8)
C100.0651 (15)0.0344 (11)0.0321 (11)0.0090 (11)0.0171 (11)0.0076 (9)
C110.0210 (8)0.0197 (8)0.0232 (9)0.0028 (7)0.0039 (7)0.0016 (7)
C120.0214 (8)0.0223 (8)0.0189 (8)0.0045 (7)0.0060 (6)0.0010 (7)
C130.0230 (9)0.0218 (9)0.0255 (9)0.0016 (7)0.0066 (7)0.0010 (7)
C140.0263 (9)0.0260 (9)0.0291 (10)0.0026 (8)0.0109 (7)0.0070 (8)
C150.0285 (9)0.0315 (10)0.0199 (9)0.0070 (8)0.0087 (7)0.0033 (8)
C160.0319 (10)0.0243 (9)0.0232 (9)0.0011 (8)0.0079 (8)0.0030 (7)
C170.0254 (9)0.0221 (9)0.0230 (9)0.0012 (7)0.0068 (7)0.0008 (7)
Geometric parameters (Å, º) top
O1—C61.3652 (19)C8—H8A0.9900
O1—C71.425 (2)C8—H8B0.9900
O2—C111.361 (2)C9—C101.309 (3)
O2—C11.4084 (19)C9—H90.9500
O3—C111.205 (2)C10—H10A0.9500
C1—C21.368 (2)C10—H10B0.9500
C1—C61.395 (2)C11—C121.487 (2)
C2—C31.397 (2)C12—C131.387 (2)
C2—H20.9500C12—C171.393 (2)
C3—C41.382 (2)C13—C141.388 (2)
C3—H30.9500C13—H130.9500
C4—C51.397 (2)C14—C151.385 (2)
C4—C81.520 (2)C14—H140.9500
C5—C61.388 (2)C15—C161.384 (2)
C5—H50.9500C15—H150.9500
C7—H7A0.9800C16—C171.387 (2)
C7—H7B0.9800C16—H160.9500
C7—H7C0.9800C17—H170.9500
C8—C91.490 (2)
C6—O1—C7116.55 (13)C4—C8—H8B108.5
C11—O2—C1116.84 (13)H8A—C8—H8B107.5
C2—C1—C6121.32 (15)C10—C9—C8124.85 (19)
C2—C1—O2119.29 (15)C10—C9—H9117.6
C6—C1—O2119.27 (14)C8—C9—H9117.6
C1—C2—C3119.82 (16)C9—C10—H10A120.0
C1—C2—H2120.1C9—C10—H10B120.0
C3—C2—H2120.1H10A—C10—H10B120.0
C4—C3—C2120.21 (16)O3—C11—O2123.18 (15)
C4—C3—H3119.9O3—C11—C12124.81 (16)
C2—C3—H3119.9O2—C11—C12112.02 (14)
C3—C4—C5119.15 (15)C13—C12—C17120.00 (15)
C3—C4—C8122.27 (15)C13—C12—C11117.65 (15)
C5—C4—C8118.58 (15)C17—C12—C11122.34 (15)
C6—C5—C4121.12 (16)C12—C13—C14119.94 (16)
C6—C5—H5119.4C12—C13—H13120.0
C4—C5—H5119.4C14—C13—H13120.0
O1—C6—C5125.55 (15)C15—C14—C13120.07 (16)
O1—C6—C1116.07 (14)C15—C14—H14120.0
C5—C6—C1118.37 (15)C13—C14—H14120.0
O1—C7—H7A109.5C16—C15—C14120.03 (16)
O1—C7—H7B109.5C16—C15—H15120.0
H7A—C7—H7B109.5C14—C15—H15120.0
O1—C7—H7C109.5C15—C16—C17120.27 (16)
H7A—C7—H7C109.5C15—C16—H16119.9
H7B—C7—H7C109.5C17—C16—H16119.9
C9—C8—C4115.06 (14)C16—C17—C12119.65 (16)
C9—C8—H8A108.5C16—C17—H17120.2
C4—C8—H8A108.5C12—C17—H17120.2
C9—C8—H8B108.5
C11—O2—C1—C2111.20 (17)C3—C4—C8—C910.0 (2)
C11—O2—C1—C672.7 (2)C5—C4—C8—C9170.21 (15)
C6—C1—C2—C30.5 (3)C4—C8—C9—C10114.8 (2)
O2—C1—C2—C3175.52 (14)C1—O2—C11—O34.8 (2)
C1—C2—C3—C40.1 (3)C1—O2—C11—C12175.22 (13)
C2—C3—C4—C50.8 (2)O3—C11—C12—C139.7 (2)
C2—C3—C4—C8178.92 (15)O2—C11—C12—C13170.29 (14)
C3—C4—C5—C61.0 (2)O3—C11—C12—C17170.28 (16)
C8—C4—C5—C6178.77 (15)O2—C11—C12—C179.7 (2)
C7—O1—C6—C54.6 (2)C17—C12—C13—C141.6 (3)
C7—O1—C6—C1174.89 (15)C11—C12—C13—C14178.36 (15)
C4—C5—C6—O1179.88 (15)C12—C13—C14—C151.2 (3)
C4—C5—C6—C10.4 (2)C13—C14—C15—C160.4 (3)
C2—C1—C6—O1179.15 (15)C14—C15—C16—C171.7 (3)
O2—C1—C6—O14.8 (2)C15—C16—C17—C121.3 (3)
C2—C1—C6—C50.4 (2)C13—C12—C17—C160.4 (3)
O2—C1—C6—C5175.68 (14)C11—C12—C17—C16179.62 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.952.553.256 (2)131
C15—H15···O3ii0.952.543.209 (2)128
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H16O3
Mr268.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)9.9334 (6), 9.5124 (5), 14.9463 (9)
β (°) 103.405 (6)
V3)1373.81 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.966, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
7024, 3168, 2242
Rint0.041
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.138, 1.05
No. of reflections3168
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.29

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.952.553.256 (2)131.3
C15—H15···O3ii0.952.543.209 (2)127.5
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+1/2, z+1/2.
 

Acknowledgements

We thank the Ministry of Higher Education of Malaysia (ERGS/1/2012/STG01/IMU/02/1; UM-C/HIR-MOHE/SC/03) for supporting this study and the International Medical University for providing the facilities.

References

First citationAgilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShibakami, M. & Sekiya, A. (1995). Acta Cryst. C51, 326–330.  CSD CrossRef CAS Web of Science IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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