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

Pichika, M.R.; Kang, Y.B.; Ng, S.W.

doi:10.1107/S1600536813015791

organic compounds

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Volume 69| Part 7| July 2013| Page o1088

https://doi.org/10.1107/S1600536813015791

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

Mallikarjuna Rao Pichika,^a ^* Yew Beng Kang ^a and Seik Weng Ng ^b,^c

^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 ).

Experimental

Crystal data

C₁₇H₁₆O₃
M_r = 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 ) T_min = 0.966, T_max = 0.983
7024 measured reflections
3168 independent reflections
2242 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.138
S = 1.05
3168 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813015791/bt6914sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015791/bt6914Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813015791/bt6914Isup3.cml

checkCIF report

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.

Structure description top

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

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

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

C₁₇H₁₆O₃	F(000) = 568
M_r = 268.30	D_x = 1.297 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1957 reflections
a = 9.9334 (6) Å	θ = 3.0–27.5°
b = 9.5124 (5) Å	µ = 0.09 mm⁻¹
c = 14.9463 (9) Å	T = 100 K
β = 103.405 (6)°	Prism, colorless
V = 1373.81 (14) Å³	0.40 × 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 Source	2242 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.041
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.0°
ω scan	h = −10→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −9→12
T_min = 0.966, T_max = 0.983	l = −19→16
7024 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0572P)² + 0.1625P] where P = (F_o² + 2F_c²)/3
3168 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₇H₁₆O₃	V = 1373.81 (14) Å³
M_r = 268.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9334 (6) Å	µ = 0.09 mm⁻¹
b = 9.5124 (5) Å	T = 100 K
c = 14.9463 (9) Å	0.40 × 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)
T_min = 0.966, T_max = 0.983	R_int = 0.041
7024 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
3168 reflections	Δρ_min = −0.29 e Å⁻³
181 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.40190 (12)	0.28310 (12)	0.60263 (8)	0.0266 (3)
O2	0.22747 (12)	0.48286 (12)	0.63406 (8)	0.0241 (3)
O3	0.09998 (13)	0.28409 (12)	0.60909 (8)	0.0266 (3)
C1	0.25534 (17)	0.47175 (17)	0.54614 (11)	0.0216 (4)
C2	0.19517 (17)	0.56488 (17)	0.47895 (12)	0.0232 (4)
H2	0.1302	0.6319	0.4904	0.028*
C3	0.22950 (17)	0.56121 (18)	0.39346 (12)	0.0236 (4)
H3	0.1877	0.6257	0.3467	0.028*
C4	0.32409 (17)	0.46399 (17)	0.37666 (11)	0.0216 (4)
C5	0.38323 (17)	0.36863 (17)	0.44573 (11)	0.0220 (4)
H5	0.4472	0.3007	0.4341	0.026*
C6	0.35012 (17)	0.37154 (17)	0.53098 (11)	0.0218 (4)
C7	0.48978 (19)	0.1729 (2)	0.58544 (13)	0.0305 (4)
H7A	0.5215	0.1171	0.6415	0.046*
H7B	0.5699	0.2133	0.5669	0.046*
H7C	0.4384	0.1124	0.5361	0.046*
C8	0.36682 (18)	0.45729 (18)	0.28547 (11)	0.0241 (4)
H8A	0.4647	0.4870	0.2957	0.029*
H8B	0.3613	0.3583	0.2645	0.029*
C9	0.2825 (2)	0.5455 (2)	0.21071 (12)	0.0300 (4)
H9	0.1877	0.5214	0.1888	0.036*
C10	0.3292 (3)	0.6537 (2)	0.17302 (14)	0.0429 (5)
H10A	0.4234	0.6809	0.1931	0.052*
H10B	0.2690	0.7049	0.1255	0.052*
C11	0.15078 (17)	0.37820 (17)	0.65969 (12)	0.0215 (4)
C12	0.13802 (17)	0.39478 (17)	0.75630 (11)	0.0206 (4)
C13	0.08089 (17)	0.28421 (18)	0.79540 (12)	0.0233 (4)
H13	0.0493	0.2026	0.7601	0.028*
C14	0.06989 (18)	0.29291 (19)	0.88614 (12)	0.0264 (4)
H14	0.0324	0.2164	0.9133	0.032*
C15	0.11346 (18)	0.41292 (18)	0.93709 (12)	0.0261 (4)
H15	0.1064	0.4185	0.9993	0.031*
C16	0.16721 (18)	0.52473 (18)	0.89742 (12)	0.0262 (4)
H16	0.1947	0.6079	0.9320	0.031*
C17	0.18109 (18)	0.51586 (18)	0.80734 (12)	0.0233 (4)
H17	0.2198	0.5920	0.7806	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0297 (7)	0.0284 (7)	0.0225 (6)	0.0055 (6)	0.0076 (5)	0.0056 (5)
O2	0.0305 (7)	0.0244 (6)	0.0196 (6)	−0.0024 (5)	0.0102 (5)	−0.0015 (5)
O3	0.0295 (7)	0.0267 (7)	0.0244 (7)	−0.0031 (6)	0.0082 (5)	−0.0049 (5)
C1	0.0244 (9)	0.0236 (9)	0.0183 (8)	−0.0042 (7)	0.0078 (7)	−0.0027 (7)
C2	0.0261 (9)	0.0196 (8)	0.0255 (9)	0.0013 (7)	0.0089 (7)	−0.0018 (7)
C3	0.0268 (9)	0.0228 (8)	0.0210 (9)	−0.0002 (8)	0.0048 (7)	0.0019 (7)
C4	0.0247 (9)	0.0211 (8)	0.0193 (8)	−0.0039 (7)	0.0054 (7)	−0.0022 (7)
C5	0.0208 (9)	0.0215 (8)	0.0251 (9)	0.0002 (7)	0.0079 (7)	0.0000 (7)
C6	0.0219 (8)	0.0215 (8)	0.0212 (8)	−0.0028 (7)	0.0032 (7)	0.0027 (7)
C7	0.0315 (10)	0.0299 (10)	0.0310 (10)	0.0054 (9)	0.0094 (8)	0.0073 (8)
C8	0.0283 (9)	0.0243 (9)	0.0210 (9)	0.0010 (8)	0.0081 (7)	0.0000 (7)
C9	0.0360 (10)	0.0338 (10)	0.0212 (9)	0.0042 (9)	0.0087 (8)	−0.0002 (8)
C10	0.0651 (15)	0.0344 (11)	0.0321 (11)	0.0090 (11)	0.0171 (11)	0.0076 (9)
C11	0.0210 (8)	0.0197 (8)	0.0232 (9)	0.0028 (7)	0.0039 (7)	0.0016 (7)
C12	0.0214 (8)	0.0223 (8)	0.0189 (8)	0.0045 (7)	0.0060 (6)	0.0010 (7)
C13	0.0230 (9)	0.0218 (9)	0.0255 (9)	0.0016 (7)	0.0066 (7)	0.0010 (7)
C14	0.0263 (9)	0.0260 (9)	0.0291 (10)	0.0026 (8)	0.0109 (7)	0.0070 (8)
C15	0.0285 (9)	0.0315 (10)	0.0199 (9)	0.0070 (8)	0.0087 (7)	0.0033 (8)
C16	0.0319 (10)	0.0243 (9)	0.0232 (9)	0.0011 (8)	0.0079 (8)	−0.0030 (7)
C17	0.0254 (9)	0.0221 (9)	0.0230 (9)	−0.0012 (7)	0.0068 (7)	0.0008 (7)

Geometric parameters (Å, º) top

O1—C6	1.3652 (19)	C8—H8A	0.9900
O1—C7	1.425 (2)	C8—H8B	0.9900
O2—C11	1.361 (2)	C9—C10	1.309 (3)
O2—C1	1.4084 (19)	C9—H9	0.9500
O3—C11	1.205 (2)	C10—H10A	0.9500
C1—C2	1.368 (2)	C10—H10B	0.9500
C1—C6	1.395 (2)	C11—C12	1.487 (2)
C2—C3	1.397 (2)	C12—C13	1.387 (2)
C2—H2	0.9500	C12—C17	1.393 (2)
C3—C4	1.382 (2)	C13—C14	1.388 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.397 (2)	C14—C15	1.385 (2)
C4—C8	1.520 (2)	C14—H14	0.9500
C5—C6	1.388 (2)	C15—C16	1.384 (2)
C5—H5	0.9500	C15—H15	0.9500
C7—H7A	0.9800	C16—C17	1.387 (2)
C7—H7B	0.9800	C16—H16	0.9500
C7—H7C	0.9800	C17—H17	0.9500
C8—C9	1.490 (2)

C6—O1—C7	116.55 (13)	C4—C8—H8B	108.5
C11—O2—C1	116.84 (13)	H8A—C8—H8B	107.5
C2—C1—C6	121.32 (15)	C10—C9—C8	124.85 (19)
C2—C1—O2	119.29 (15)	C10—C9—H9	117.6
C6—C1—O2	119.27 (14)	C8—C9—H9	117.6
C1—C2—C3	119.82 (16)	C9—C10—H10A	120.0
C1—C2—H2	120.1	C9—C10—H10B	120.0
C3—C2—H2	120.1	H10A—C10—H10B	120.0
C4—C3—C2	120.21 (16)	O3—C11—O2	123.18 (15)
C4—C3—H3	119.9	O3—C11—C12	124.81 (16)
C2—C3—H3	119.9	O2—C11—C12	112.02 (14)
C3—C4—C5	119.15 (15)	C13—C12—C17	120.00 (15)
C3—C4—C8	122.27 (15)	C13—C12—C11	117.65 (15)
C5—C4—C8	118.58 (15)	C17—C12—C11	122.34 (15)
C6—C5—C4	121.12 (16)	C12—C13—C14	119.94 (16)
C6—C5—H5	119.4	C12—C13—H13	120.0
C4—C5—H5	119.4	C14—C13—H13	120.0
O1—C6—C5	125.55 (15)	C15—C14—C13	120.07 (16)
O1—C6—C1	116.07 (14)	C15—C14—H14	120.0
C5—C6—C1	118.37 (15)	C13—C14—H14	120.0
O1—C7—H7A	109.5	C16—C15—C14	120.03 (16)
O1—C7—H7B	109.5	C16—C15—H15	120.0
H7A—C7—H7B	109.5	C14—C15—H15	120.0
O1—C7—H7C	109.5	C15—C16—C17	120.27 (16)
H7A—C7—H7C	109.5	C15—C16—H16	119.9
H7B—C7—H7C	109.5	C17—C16—H16	119.9
C9—C8—C4	115.06 (14)	C16—C17—C12	119.65 (16)
C9—C8—H8A	108.5	C16—C17—H17	120.2
C4—C8—H8A	108.5	C12—C17—H17	120.2
C9—C8—H8B	108.5

C11—O2—C1—C2	111.20 (17)	C3—C4—C8—C9	−10.0 (2)
C11—O2—C1—C6	−72.7 (2)	C5—C4—C8—C9	170.21 (15)
C6—C1—C2—C3	−0.5 (3)	C4—C8—C9—C10	114.8 (2)
O2—C1—C2—C3	175.52 (14)	C1—O2—C11—O3	−4.8 (2)
C1—C2—C3—C4	−0.1 (3)	C1—O2—C11—C12	175.22 (13)
C2—C3—C4—C5	0.8 (2)	O3—C11—C12—C13	9.7 (2)
C2—C3—C4—C8	−178.92 (15)	O2—C11—C12—C13	−170.29 (14)
C3—C4—C5—C6	−1.0 (2)	O3—C11—C12—C17	−170.28 (16)
C8—C4—C5—C6	178.77 (15)	O2—C11—C12—C17	9.7 (2)
C7—O1—C6—C5	−4.6 (2)	C17—C12—C13—C14	−1.6 (3)
C7—O1—C6—C1	174.89 (15)	C11—C12—C13—C14	178.36 (15)
C4—C5—C6—O1	179.88 (15)	C12—C13—C14—C15	1.2 (3)
C4—C5—C6—C1	0.4 (2)	C13—C14—C15—C16	0.4 (3)
C2—C1—C6—O1	−179.15 (15)	C14—C15—C16—C17	−1.7 (3)
O2—C1—C6—O1	4.8 (2)	C15—C16—C17—C12	1.3 (3)
C2—C1—C6—C5	0.4 (2)	C13—C12—C17—C16	0.4 (3)
O2—C1—C6—C5	−175.68 (14)	C11—C12—C17—C16	−179.62 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₃
M_r	268.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.9334 (6), 9.5124 (5), 14.9463 (9)
β (°)	103.405 (6)
V (Å³)	1373.81 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.966, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	7024, 3168, 2242
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.138, 1.05
No. of reflections	3168
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.95	2.55	3.256 (2)	131.3
C15—H15···O3ⁱⁱ	0.95	2.54	3.209 (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

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