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

Abstract

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,

• a = 9.9334 (6) Å

• b = 9.5124 (5) Å

• c = 14.9463 (9) Å

• β = 103.405 (6)°

• V = 1373.81 (14) ų

• 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[F ² > 2σ(F ²)] = 0.051

• wR(F ²) = 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

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 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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) ; (ii) .

supplementary crystallographic information

Comment

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).

Experimental

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

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

Figures

Fig. 1.

Thermal ellipsoid plot (Barbour, 2001) of C17H16O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H16O3	F(000) = 568
Mr = 268.30	Dx = 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

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	Rint = 0.041
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.0°
ω scan	h = −10→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −9→12
Tmin = 0.966, Tmax = 0.983	l = −19→16
7024 measured reflections

Refinement

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(Fo2) + (0.0572P)2 + 0.1625P] where P = (Fo2 + 2Fc2)/3
3168 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)

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.