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

Abstract

In the title compound, C₁₈H₁₈O₄, the planes of the benzene rings are twisted by 81.60 (5)°. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into supra­molecular chains extending along the a axis.

Related literature  

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

Experimental  

Crystal data  

• C₁₈H₁₈O₄

• M _r = 298.32

• Triclinic,

• a = 8.7685 (6) Å

• b = 9.8159 (7) Å

• c = 10.3515 (6) Å

• α = 113.030 (6)°

• β = 101.231 (6)°

• γ = 102.378 (6)°

• V = 761.45 (11) ų

• Z = 2

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 100 K

• 0.40 × 0.40 × 0.20 mm

Data collection  

• Agilent SuperNova Dual diffractometer with an Atlas detector

• Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T _min = 0.964, T _max = 0.982

• 6267 measured reflections

• 3525 independent reflections

• 2497 reflections with I > 2σ(I)

• R _int = 0.027

Refinement  

• R[F ² > 2σ(F ²)] = 0.050

• wR(F ²) = 0.132

• S = 1.06

• 3525 reflections

• 199 parameters

• H-atom parameters constrained

• Δρ_max = 0.47 e Å⁻³

• Δρ_min = −0.24 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
C18—H18B⋯O3i	0.98	2.54	3.458 (2)	156

Symmetry code: (i) .

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 81.60 (5)°]. The twist is similar to that found in the unsubstituted compound, phenyl benzoate (Shibakami & Sekiya, 1995). In the crystal, weak C—H···O hydrogen bond links molecules into the supramolecular chains extending along the a axis (Table 1).

Experimental

4-Allyl-2-methoxyphenol (1 mmol), 4-methoxybenzoic 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

Carbon-bound 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 C18H18O4 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H18O4	Z = 2
Mr = 298.32	F(000) = 316
Triclinic, P1	Dx = 1.301 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7685 (6) Å	Cell parameters from 2058 reflections
b = 9.8159 (7) Å	θ = 3.4–27.5°
c = 10.3515 (6) Å	µ = 0.09 mm−1
α = 113.030 (6)°	T = 100 K
β = 101.231 (6)°	Prism, colorless
γ = 102.378 (6)°	0.40 × 0.40 × 0.20 mm
V = 761.45 (11) Å3

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector	3525 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2497 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.4°
ω scan	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −11→12
Tmin = 0.964, Tmax = 0.982	l = −13→13
6267 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.0956P] where P = (Fo2 + 2Fc2)/3
3525 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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

	x	y	z	Uiso*/Ueq
O1	0.25854 (15)	0.56195 (13)	0.97044 (12)	0.0239 (3)
O2	0.17691 (14)	0.49329 (12)	0.68408 (12)	0.0201 (3)
O3	0.03197 (15)	0.26310 (13)	0.66616 (13)	0.0242 (3)
O4	0.54829 (15)	0.06265 (13)	0.33989 (13)	0.0245 (3)
C1	0.1367 (2)	0.61293 (18)	0.92258 (18)	0.0198 (4)
C2	0.0589 (2)	0.70167 (19)	1.01000 (18)	0.0212 (4)
H2	0.0890	0.7300	1.1126	0.025*
C3	−0.0628 (2)	0.75000 (19)	0.94958 (18)	0.0223 (4)
C4	−0.1092 (2)	0.70584 (19)	0.79870 (18)	0.0228 (4)
H4	−0.1929	0.7373	0.7565	0.027*
C5	−0.0329 (2)	0.61580 (19)	0.70993 (18)	0.0208 (4)
H5	−0.0646	0.5852	0.6069	0.025*
C6	0.0886 (2)	0.57120 (18)	0.77169 (17)	0.0186 (4)
C7	0.3292 (2)	0.6251 (2)	1.12758 (18)	0.0273 (4)
H7A	0.4173	0.5827	1.1487	0.041*
H7B	0.2443	0.5963	1.1700	0.041*
H7C	0.3742	0.7392	1.1712	0.041*
C8	−0.1423 (2)	0.8524 (2)	1.0485 (2)	0.0285 (4)
H8A	−0.0931	0.8723	1.1514	0.034*
H8B	−0.1166	0.9544	1.0460	0.034*
C9	−0.3225 (2)	0.7840 (2)	1.0064 (2)	0.0342 (5)
H9	−0.3629	0.6969	1.0236	0.041*
C10	−0.4308 (3)	0.8330 (3)	0.9476 (2)	0.0412 (5)
H10A	−0.3957	0.9198	0.9284	0.049*
H10B	−0.5447	0.7819	0.9239	0.049*
C11	0.1434 (2)	0.33704 (18)	0.64360 (17)	0.0181 (4)
C12	0.2555 (2)	0.27352 (18)	0.56621 (17)	0.0179 (4)
C13	0.2089 (2)	0.11166 (19)	0.47938 (18)	0.0232 (4)
H13	0.1070	0.0463	0.4717	0.028*
C14	0.3087 (2)	0.04630 (19)	0.40522 (19)	0.0241 (4)
H14	0.2745	−0.0635	0.3452	0.029*
C15	0.4596 (2)	0.14002 (19)	0.41746 (17)	0.0195 (4)
C16	0.5092 (2)	0.30149 (19)	0.50483 (18)	0.0210 (4)
H16	0.6126	0.3663	0.5146	0.025*
C17	0.4059 (2)	0.36649 (18)	0.57741 (17)	0.0193 (4)
H17	0.4387	0.4765	0.6357	0.023*
C18	0.7088 (2)	0.1525 (2)	0.3554 (2)	0.0301 (4)
H18A	0.7575	0.0844	0.2908	0.045*
H18B	0.7782	0.1986	0.4582	0.045*
H18C	0.7004	0.2360	0.3277	0.045*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0262 (7)	0.0270 (6)	0.0171 (6)	0.0127 (5)	0.0042 (5)	0.0077 (5)
O2	0.0243 (6)	0.0178 (6)	0.0196 (6)	0.0080 (5)	0.0107 (5)	0.0073 (5)
O3	0.0241 (7)	0.0222 (6)	0.0247 (7)	0.0046 (5)	0.0117 (5)	0.0085 (5)
O4	0.0221 (6)	0.0247 (6)	0.0262 (7)	0.0084 (5)	0.0119 (5)	0.0084 (5)
C1	0.0212 (9)	0.0180 (8)	0.0202 (9)	0.0055 (7)	0.0055 (7)	0.0096 (7)
C2	0.0226 (9)	0.0209 (8)	0.0157 (8)	0.0050 (7)	0.0050 (7)	0.0055 (7)
C3	0.0213 (9)	0.0214 (8)	0.0228 (9)	0.0062 (7)	0.0103 (7)	0.0075 (7)
C4	0.0223 (9)	0.0245 (9)	0.0225 (9)	0.0085 (7)	0.0054 (8)	0.0118 (7)
C5	0.0229 (9)	0.0227 (8)	0.0168 (8)	0.0057 (7)	0.0065 (7)	0.0095 (7)
C6	0.0205 (8)	0.0167 (8)	0.0188 (8)	0.0054 (7)	0.0091 (7)	0.0069 (7)
C7	0.0290 (10)	0.0306 (10)	0.0190 (9)	0.0110 (8)	0.0017 (8)	0.0098 (8)
C8	0.0293 (10)	0.0308 (10)	0.0227 (9)	0.0136 (8)	0.0096 (8)	0.0067 (8)
C9	0.0378 (12)	0.0304 (10)	0.0362 (11)	0.0124 (9)	0.0209 (10)	0.0114 (9)
C10	0.0325 (11)	0.0520 (13)	0.0377 (12)	0.0177 (10)	0.0126 (10)	0.0161 (10)
C11	0.0198 (8)	0.0185 (8)	0.0133 (8)	0.0050 (7)	0.0026 (7)	0.0062 (6)
C12	0.0182 (8)	0.0192 (8)	0.0152 (8)	0.0052 (7)	0.0047 (7)	0.0072 (6)
C13	0.0216 (9)	0.0206 (8)	0.0240 (9)	0.0024 (7)	0.0086 (8)	0.0084 (7)
C14	0.0266 (9)	0.0171 (8)	0.0244 (9)	0.0047 (7)	0.0103 (8)	0.0052 (7)
C15	0.0204 (8)	0.0229 (8)	0.0174 (8)	0.0102 (7)	0.0065 (7)	0.0094 (7)
C16	0.0178 (8)	0.0208 (8)	0.0226 (9)	0.0021 (7)	0.0045 (7)	0.0110 (7)
C17	0.0210 (9)	0.0165 (8)	0.0173 (8)	0.0052 (7)	0.0041 (7)	0.0060 (7)
C18	0.0219 (9)	0.0332 (10)	0.0345 (11)	0.0083 (8)	0.0148 (8)	0.0119 (8)

Geometric parameters (Å, º)

O1—C1	1.362 (2)	C8—H8A	0.9900
O1—C7	1.4381 (19)	C8—H8B	0.9900
O2—C11	1.3676 (19)	C9—C10	1.306 (3)
O2—C6	1.4110 (19)	C9—H9	0.9500
O3—C11	1.205 (2)	C10—H10A	0.9500
O4—C15	1.358 (2)	C10—H10B	0.9500
O4—C18	1.433 (2)	C11—C12	1.475 (2)
C1—C2	1.386 (2)	C12—C17	1.388 (2)
C1—C6	1.398 (2)	C12—C13	1.400 (2)
C2—C3	1.395 (2)	C13—C14	1.372 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.393 (2)	C14—C15	1.391 (2)
C3—C8	1.522 (2)	C14—H14	0.9500
C4—C5	1.389 (2)	C15—C16	1.396 (2)
C4—H4	0.9500	C16—C17	1.390 (2)
C5—C6	1.375 (2)	C16—H16	0.9500
C5—H5	0.9500	C17—H17	0.9500
C7—H7A	0.9800	C18—H18A	0.9800
C7—H7B	0.9800	C18—H18B	0.9800
C7—H7C	0.9800	C18—H18C	0.9800
C8—C9	1.478 (3)
C1—O1—C7	116.79 (13)	C10—C9—C8	125.6 (2)
C11—O2—C6	116.91 (13)	C10—C9—H9	117.2
C15—O4—C18	117.48 (13)	C8—C9—H9	117.2
O1—C1—C2	125.77 (15)	C9—C10—H10A	120.0
O1—C1—C6	115.87 (14)	C9—C10—H10B	120.0
C2—C1—C6	118.36 (15)	H10A—C10—H10B	120.0
C1—C2—C3	120.95 (16)	O3—C11—O2	122.70 (15)
C1—C2—H2	119.5	O3—C11—C12	125.80 (15)
C3—C2—H2	119.5	O2—C11—C12	111.46 (14)
C4—C3—C2	119.50 (16)	C17—C12—C13	118.63 (15)
C4—C3—C8	120.39 (16)	C17—C12—C11	123.04 (14)
C2—C3—C8	120.10 (15)	C13—C12—C11	118.32 (15)
C5—C4—C3	119.97 (16)	C14—C13—C12	120.75 (16)
C5—C4—H4	120.0	C14—C13—H13	119.6
C3—C4—H4	120.0	C12—C13—H13	119.6
C6—C5—C4	119.76 (15)	C13—C14—C15	120.34 (15)
C6—C5—H5	120.1	C13—C14—H14	119.8
C4—C5—H5	120.1	C15—C14—H14	119.8
C5—C6—C1	121.45 (15)	O4—C15—C14	115.22 (14)
C5—C6—O2	119.49 (14)	O4—C15—C16	125.00 (15)
C1—C6—O2	118.84 (14)	C14—C15—C16	119.78 (15)
O1—C7—H7A	109.5	C17—C16—C15	119.31 (15)
O1—C7—H7B	109.5	C17—C16—H16	120.3
H7A—C7—H7B	109.5	C15—C16—H16	120.3
O1—C7—H7C	109.5	C12—C17—C16	121.17 (15)
H7A—C7—H7C	109.5	C12—C17—H17	119.4
H7B—C7—H7C	109.5	C16—C17—H17	119.4
C9—C8—C3	114.01 (15)	O4—C18—H18A	109.5
C9—C8—H8A	108.8	O4—C18—H18B	109.5
C3—C8—H8A	108.7	H18A—C18—H18B	109.5
C9—C8—H8B	108.7	O4—C18—H18C	109.5
C3—C8—H8B	108.7	H18A—C18—H18C	109.5
H8A—C8—H8B	107.6	H18B—C18—H18C	109.5
C7—O1—C1—C2	−9.9 (2)	C3—C8—C9—C10	−109.0 (2)
C7—O1—C1—C6	169.69 (14)	C6—O2—C11—O3	8.1 (2)
O1—C1—C2—C3	178.83 (15)	C6—O2—C11—C12	−173.97 (12)
C6—C1—C2—C3	−0.8 (2)	O3—C11—C12—C17	−161.98 (17)
C1—C2—C3—C4	1.3 (3)	O2—C11—C12—C17	20.1 (2)
C1—C2—C3—C8	−177.75 (16)	O3—C11—C12—C13	17.0 (2)
C2—C3—C4—C5	−0.7 (3)	O2—C11—C12—C13	−160.88 (14)
C8—C3—C4—C5	178.28 (15)	C17—C12—C13—C14	−0.9 (3)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—C14	−179.88 (15)
C4—C5—C6—C1	0.7 (3)	C12—C13—C14—C15	1.2 (3)
C4—C5—C6—O2	−173.71 (14)	C18—O4—C15—C14	−176.50 (15)
O1—C1—C6—C5	−179.87 (15)	C18—O4—C15—C16	3.6 (2)
C2—C1—C6—C5	−0.2 (2)	C13—C14—C15—O4	179.68 (16)
O1—C1—C6—O2	−5.4 (2)	C13—C14—C15—C16	−0.5 (3)
C2—C1—C6—O2	174.27 (14)	O4—C15—C16—C17	179.26 (15)
C11—O2—C6—C5	−107.13 (17)	C14—C15—C16—C17	−0.6 (2)
C11—O2—C6—C1	78.29 (18)	C13—C12—C17—C16	−0.2 (2)
C4—C3—C8—C9	59.1 (2)	C11—C12—C17—C16	178.76 (15)
C2—C3—C8—C9	−121.88 (19)	C15—C16—C17—C12	0.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O3i	0.98	2.54	3.458 (2)	156

Symmetry code: (i) x+1, y, z.