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

Pichika, M.R.; Yew, B.K.; Ng, S.W.

doi:10.1107/S1600536813011458

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o819

doi:10.1107/S1600536813011458

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

Mallikarjuna Rao Pichika,^a Beng Kang Yew ^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: seikweng@um.edu.my

(Received 26 April 2013; accepted 26 April 2013; online 4 May 2013)

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, $[P \overline 1]$
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) Å³
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[F² > 2σ(F²)] = 0.050
wR(F²) = 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

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) x+1, y, z.

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: 10.1107/S1600536813011458/xu5699sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813011458/xu5699Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813011458/xu5699Isup3.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 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).

Related literature top

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

Experimental top

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.

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

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

Crystal data top

C₁₈H₁₈O₄	Z = 2
M_r = 298.32	F(000) = 316
Triclinic, P1	D_x = 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 top

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	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.4°
ω scan	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −11→12
T_min = 0.964, T_max = 0.982	l = −13→13
6267 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0533P)² + 0.0956P] where P = (F_o² + 2F_c²)/3
3525 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₈O₄	γ = 102.378 (6)°
M_r = 298.32	V = 761.45 (11) Å³
Triclinic, P1	Z = 2
a = 8.7685 (6) Å	Mo Kα radiation
b = 9.8159 (7) Å	µ = 0.09 mm⁻¹
c = 10.3515 (6) Å	T = 100 K
α = 113.030 (6)°	0.40 × 0.40 × 0.20 mm
β = 101.231 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3525 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	2497 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.982	R_int = 0.027
6267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.06	Δρ_max = 0.47 e Å⁻³
3525 reflections	Δρ_min = −0.24 e Å⁻³
199 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₄
M_r	298.32
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.7685 (6), 9.8159 (7), 10.3515 (6)
α, β, γ (°)	113.030 (6), 101.231 (6), 102.378 (6)
V (Å³)	761.45 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.40 × 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	0.964, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	6267, 3525, 2497
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.132, 1.06
No. of reflections	3525
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.24

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

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

Acknowledgements

We thank the International Medical University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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