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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813011458/xu5699sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536813011458/xu5699Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813011458/xu5699Isup3.cml
Supplementary material

CCDC reference: 954866

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.132
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 6
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00600 Deg.
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

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.

Refinement top

Carbon-bound 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 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
C18H18O4Z = 2
Mr = 298.32F(000) = 316
Triclinic, P1Dx = 1.301 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7685 (6) ÅCell parameters from 2058 reflections
b = 9.8159 (7) Åθ = 3.4–27.5°
c = 10.3515 (6) ŵ = 0.09 mm1
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 Source2497 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.027
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 3.4°
ω scanh = 118
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1112
Tmin = 0.964, Tmax = 0.982l = 1313
6267 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-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 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C18H18O4γ = 102.378 (6)°
Mr = 298.32V = 761.45 (11) Å3
Triclinic, P1Z = 2
a = 8.7685 (6) ÅMo Kα radiation
b = 9.8159 (7) ŵ = 0.09 mm1
c = 10.3515 (6) ÅT = 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)
Tmin = 0.964, Tmax = 0.982Rint = 0.027
6267 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.06Δρmax = 0.47 e Å3
3525 reflectionsΔρmin = 0.24 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.25854 (15)0.56195 (13)0.97044 (12)0.0239 (3)
O20.17691 (14)0.49329 (12)0.68408 (12)0.0201 (3)
O30.03197 (15)0.26310 (13)0.66616 (13)0.0242 (3)
O40.54829 (15)0.06265 (13)0.33989 (13)0.0245 (3)
C10.1367 (2)0.61293 (18)0.92258 (18)0.0198 (4)
C20.0589 (2)0.70167 (19)1.01000 (18)0.0212 (4)
H20.08900.73001.11260.025*
C30.0628 (2)0.75000 (19)0.94958 (18)0.0223 (4)
C40.1092 (2)0.70584 (19)0.79870 (18)0.0228 (4)
H40.19290.73730.75650.027*
C50.0329 (2)0.61580 (19)0.70993 (18)0.0208 (4)
H50.06460.58520.60690.025*
C60.0886 (2)0.57120 (18)0.77169 (17)0.0186 (4)
C70.3292 (2)0.6251 (2)1.12758 (18)0.0273 (4)
H7A0.41730.58271.14870.041*
H7B0.24430.59631.17000.041*
H7C0.37420.73921.17120.041*
C80.1423 (2)0.8524 (2)1.0485 (2)0.0285 (4)
H8A0.09310.87231.15140.034*
H8B0.11660.95441.04600.034*
C90.3225 (2)0.7840 (2)1.0064 (2)0.0342 (5)
H90.36290.69691.02360.041*
C100.4308 (3)0.8330 (3)0.9476 (2)0.0412 (5)
H10A0.39570.91980.92840.049*
H10B0.54470.78190.92390.049*
C110.1434 (2)0.33704 (18)0.64360 (17)0.0181 (4)
C120.2555 (2)0.27352 (18)0.56621 (17)0.0179 (4)
C130.2089 (2)0.11166 (19)0.47938 (18)0.0232 (4)
H130.10700.04630.47170.028*
C140.3087 (2)0.04630 (19)0.40522 (19)0.0241 (4)
H140.27450.06350.34520.029*
C150.4596 (2)0.14002 (19)0.41746 (17)0.0195 (4)
C160.5092 (2)0.30149 (19)0.50483 (18)0.0210 (4)
H160.61260.36630.51460.025*
C170.4059 (2)0.36649 (18)0.57741 (17)0.0193 (4)
H170.43870.47650.63570.023*
C180.7088 (2)0.1525 (2)0.3554 (2)0.0301 (4)
H18A0.75750.08440.29080.045*
H18B0.77820.19860.45820.045*
H18C0.70040.23600.32770.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0262 (7)0.0270 (6)0.0171 (6)0.0127 (5)0.0042 (5)0.0077 (5)
O20.0243 (6)0.0178 (6)0.0196 (6)0.0080 (5)0.0107 (5)0.0073 (5)
O30.0241 (7)0.0222 (6)0.0247 (7)0.0046 (5)0.0117 (5)0.0085 (5)
O40.0221 (6)0.0247 (6)0.0262 (7)0.0084 (5)0.0119 (5)0.0084 (5)
C10.0212 (9)0.0180 (8)0.0202 (9)0.0055 (7)0.0055 (7)0.0096 (7)
C20.0226 (9)0.0209 (8)0.0157 (8)0.0050 (7)0.0050 (7)0.0055 (7)
C30.0213 (9)0.0214 (8)0.0228 (9)0.0062 (7)0.0103 (7)0.0075 (7)
C40.0223 (9)0.0245 (9)0.0225 (9)0.0085 (7)0.0054 (8)0.0118 (7)
C50.0229 (9)0.0227 (8)0.0168 (8)0.0057 (7)0.0065 (7)0.0095 (7)
C60.0205 (8)0.0167 (8)0.0188 (8)0.0054 (7)0.0091 (7)0.0069 (7)
C70.0290 (10)0.0306 (10)0.0190 (9)0.0110 (8)0.0017 (8)0.0098 (8)
C80.0293 (10)0.0308 (10)0.0227 (9)0.0136 (8)0.0096 (8)0.0067 (8)
C90.0378 (12)0.0304 (10)0.0362 (11)0.0124 (9)0.0209 (10)0.0114 (9)
C100.0325 (11)0.0520 (13)0.0377 (12)0.0177 (10)0.0126 (10)0.0161 (10)
C110.0198 (8)0.0185 (8)0.0133 (8)0.0050 (7)0.0026 (7)0.0062 (6)
C120.0182 (8)0.0192 (8)0.0152 (8)0.0052 (7)0.0047 (7)0.0072 (6)
C130.0216 (9)0.0206 (8)0.0240 (9)0.0024 (7)0.0086 (8)0.0084 (7)
C140.0266 (9)0.0171 (8)0.0244 (9)0.0047 (7)0.0103 (8)0.0052 (7)
C150.0204 (8)0.0229 (8)0.0174 (8)0.0102 (7)0.0065 (7)0.0094 (7)
C160.0178 (8)0.0208 (8)0.0226 (9)0.0021 (7)0.0045 (7)0.0110 (7)
C170.0210 (9)0.0165 (8)0.0173 (8)0.0052 (7)0.0041 (7)0.0060 (7)
C180.0219 (9)0.0332 (10)0.0345 (11)0.0083 (8)0.0148 (8)0.0119 (8)
Geometric parameters (Å, º) top
O1—C11.362 (2)C8—H8A0.9900
O1—C71.4381 (19)C8—H8B0.9900
O2—C111.3676 (19)C9—C101.306 (3)
O2—C61.4110 (19)C9—H90.9500
O3—C111.205 (2)C10—H10A0.9500
O4—C151.358 (2)C10—H10B0.9500
O4—C181.433 (2)C11—C121.475 (2)
C1—C21.386 (2)C12—C171.388 (2)
C1—C61.398 (2)C12—C131.400 (2)
C2—C31.395 (2)C13—C141.372 (2)
C2—H20.9500C13—H130.9500
C3—C41.393 (2)C14—C151.391 (2)
C3—C81.522 (2)C14—H140.9500
C4—C51.389 (2)C15—C161.396 (2)
C4—H40.9500C16—C171.390 (2)
C5—C61.375 (2)C16—H160.9500
C5—H50.9500C17—H170.9500
C7—H7A0.9800C18—H18A0.9800
C7—H7B0.9800C18—H18B0.9800
C7—H7C0.9800C18—H18C0.9800
C8—C91.478 (3)
C1—O1—C7116.79 (13)C10—C9—C8125.6 (2)
C11—O2—C6116.91 (13)C10—C9—H9117.2
C15—O4—C18117.48 (13)C8—C9—H9117.2
O1—C1—C2125.77 (15)C9—C10—H10A120.0
O1—C1—C6115.87 (14)C9—C10—H10B120.0
C2—C1—C6118.36 (15)H10A—C10—H10B120.0
C1—C2—C3120.95 (16)O3—C11—O2122.70 (15)
C1—C2—H2119.5O3—C11—C12125.80 (15)
C3—C2—H2119.5O2—C11—C12111.46 (14)
C4—C3—C2119.50 (16)C17—C12—C13118.63 (15)
C4—C3—C8120.39 (16)C17—C12—C11123.04 (14)
C2—C3—C8120.10 (15)C13—C12—C11118.32 (15)
C5—C4—C3119.97 (16)C14—C13—C12120.75 (16)
C5—C4—H4120.0C14—C13—H13119.6
C3—C4—H4120.0C12—C13—H13119.6
C6—C5—C4119.76 (15)C13—C14—C15120.34 (15)
C6—C5—H5120.1C13—C14—H14119.8
C4—C5—H5120.1C15—C14—H14119.8
C5—C6—C1121.45 (15)O4—C15—C14115.22 (14)
C5—C6—O2119.49 (14)O4—C15—C16125.00 (15)
C1—C6—O2118.84 (14)C14—C15—C16119.78 (15)
O1—C7—H7A109.5C17—C16—C15119.31 (15)
O1—C7—H7B109.5C17—C16—H16120.3
H7A—C7—H7B109.5C15—C16—H16120.3
O1—C7—H7C109.5C12—C17—C16121.17 (15)
H7A—C7—H7C109.5C12—C17—H17119.4
H7B—C7—H7C109.5C16—C17—H17119.4
C9—C8—C3114.01 (15)O4—C18—H18A109.5
C9—C8—H8A108.8O4—C18—H18B109.5
C3—C8—H8A108.7H18A—C18—H18B109.5
C9—C8—H8B108.7O4—C18—H18C109.5
C3—C8—H8B108.7H18A—C18—H18C109.5
H8A—C8—H8B107.6H18B—C18—H18C109.5
C7—O1—C1—C29.9 (2)C3—C8—C9—C10109.0 (2)
C7—O1—C1—C6169.69 (14)C6—O2—C11—O38.1 (2)
O1—C1—C2—C3178.83 (15)C6—O2—C11—C12173.97 (12)
C6—C1—C2—C30.8 (2)O3—C11—C12—C17161.98 (17)
C1—C2—C3—C41.3 (3)O2—C11—C12—C1720.1 (2)
C1—C2—C3—C8177.75 (16)O3—C11—C12—C1317.0 (2)
C2—C3—C4—C50.7 (3)O2—C11—C12—C13160.88 (14)
C8—C3—C4—C5178.28 (15)C17—C12—C13—C140.9 (3)
C3—C4—C5—C60.3 (3)C11—C12—C13—C14179.88 (15)
C4—C5—C6—C10.7 (3)C12—C13—C14—C151.2 (3)
C4—C5—C6—O2173.71 (14)C18—O4—C15—C14176.50 (15)
O1—C1—C6—C5179.87 (15)C18—O4—C15—C163.6 (2)
C2—C1—C6—C50.2 (2)C13—C14—C15—O4179.68 (16)
O1—C1—C6—O25.4 (2)C13—C14—C15—C160.5 (3)
C2—C1—C6—O2174.27 (14)O4—C15—C16—C17179.26 (15)
C11—O2—C6—C5107.13 (17)C14—C15—C16—C170.6 (2)
C11—O2—C6—C178.29 (18)C13—C12—C17—C160.2 (2)
C4—C3—C8—C959.1 (2)C11—C12—C17—C16178.76 (15)
C2—C3—C8—C9121.88 (19)C15—C16—C17—C120.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18B···O3i0.982.543.458 (2)156
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC18H18O4
Mr298.32
Crystal system, space groupTriclinic, 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)
V3)761.45 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.40 × 0.20
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2013)
Tmin, Tmax0.964, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
6267, 3525, 2497
Rint0.027
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.132, 1.06
No. of reflections3525
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C18—H18B···O3i0.982.543.458 (2)156
Symmetry code: (i) x+1, y, z.
 

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