2-Isopropyl-4-meth­oxy-5-methyl­phenyl benzoate

Moumou, M.; Akssira, M.; Elhakmaoui, A.; El Ammari, L.; Benharref, A.; Berraho, M.

doi:10.1107/S160053681000930X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o850

doi:10.1107/S160053681000930X

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2-Isopropyl-4-methoxy-5-methylphenyl benzoate

Mohamed Moumou,^a Mohamed Akssira,^a Ahmed Elhakmaoui,^a Lahcen El Ammari,^b Ahmed Benharref ^c and Moha Berraho ^c ^*

^aLaboratoire de Chimie Bioorganique et Analytique, URAC 22, Faculté des Sciences et Techniques, 20800 Mohammedia, Morocco, ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Avenue Ibn Battouta BP 1014 Rabat, Morocco, and ^cLaboratoire de Chimie Biomolécules, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390 Bd My abdellah, 40000 Marrakech, Morocco
^*Correspondence e-mail: mberraho@yahoo.fr

(Received 4 March 2010; accepted 11 March 2010; online 17 March 2010)

The title compound, C₁₈H₂₀O₃, a hemisynthetic product, was obtained by the reaction of benzoyl chloride and p-methoxythymol. The structure comprises two benzene rings bridged by a carboxyl group; the dihedral angle between the rings is 73.54 (8)°.

Related literature

For background to the phytochemical study of Moroccan plants, see: Barrero et al. (2005 ); Zrira et al. (2005 ). For background to the medicinal interest in Tetraclinis artculata, from which the title compound was extracted, see: Aitigri et al. (1990 ).

Experimental

Crystal data

C₁₈H₂₀O₃
M_r = 284.34
Monoclinic, P 2₁ /n
a = 8.4765 (4) Å
b = 8.0880 (4) Å
c = 23.8119 (11) Å
β = 98.202 (2)°
V = 1615.80 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.27 × 0.17 × 0.12 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer
14992 measured reflections
2912 independent reflections
2302 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.02
2912 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000930X/tk2638sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000930X/tk2638Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was investigated as a part of our study of essential oils isolated from the sawdust of Tetraclinis articulata originating from the region of Essaouira in Morocco (Aitigri et al., 1990; Barrero et al., 2005; Zrira et al., 2005). In this paper, we present the crystal structure of (I), which was synthesised by the reaction of the benzoyl chloride and p-methoxythymol (see Experimental). The molecular structure of (I), Fig. 1, shows the two benzene rings are almost perpendicular with the dihedral angle between them being 73.54 (8)°.

Related literature top

For background to the phytochemical study of Moroccan plants, see: Barrero et al. (2005); Zrira et al. (2005). For background to the medicinal interest in Tetraclinis artculata, from which the title compound was extracted, see: Aitigri et al. (1990).

Experimental top

The Tetraclinis articulata (Vahl) Masters was collected in the region of Essaouira (Morocco). Wood sawdust was hydro-distilled in a Clevenger-type apparatus for 6 h to produce essential oils in 3% yield. The oil was then extracted by diethylether, dried over Mg₂SO₄, and the solvent evaporated. The oil was then subjected to silica gel column chromatography by eluting with hexane-ethyl acetate (98:2). The fifth fraction contained p-methoxythymol as the major compound. The structure of this product was confirmed by reaction with benzoyl chloride (0.74 g, 5.3 mmol) and crude fifth fraction (0.8 g) in a solution of 10% NaOH (50 ml). The mixture was left under agitation at 298 K for 1 h. The resulting crystalline precipitate was filtered and recrystallized from methanol. The air-dried crystal (0.7 g) had a melting point of 259–260 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

2-Isopropyl-4-methoxy-5-methylphenyl benzoate top

Crystal data top

C₁₈H₂₀O₃	F(000) = 608
M_r = 284.34	D_x = 1.169 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 14992 reflections
a = 8.4765 (4) Å	θ = 2.5–25.2°
b = 8.0880 (4) Å	µ = 0.08 mm⁻¹
c = 23.8119 (11) Å	T = 298 K
β = 98.202 (2)°	Prism, colourless
V = 1615.80 (13) Å³	0.27 × 0.17 × 0.12 mm
Z = 4

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	2302 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 25.2°, θ_min = 2.5°
ϕ and ω scans	h = −10→10
14992 measured reflections	k = −9→9
2912 independent reflections	l = −28→28

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0574P)² + 0.3991P] where P = (F_o² + 2F_c²)/3
2912 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₂₀O₃	V = 1615.80 (13) Å³
M_r = 284.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4765 (4) Å	µ = 0.08 mm⁻¹
b = 8.0880 (4) Å	T = 298 K
c = 23.8119 (11) Å	0.27 × 0.17 × 0.12 mm
β = 98.202 (2)°

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	2302 reflections with I > 2σ(I)
14992 measured reflections	R_int = 0.028
2912 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
2912 reflections	Δρ_min = −0.18 e Å⁻³
194 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.77989 (18)	0.64673 (18)	0.08713 (6)	0.0432 (4)
C2	0.69644 (17)	0.56847 (18)	0.12520 (6)	0.0430 (4)
C3	0.62554 (18)	0.41749 (19)	0.10781 (6)	0.0474 (4)
H3	0.5675	0.3612	0.1321	0.057*
C4	0.63938 (18)	0.34959 (19)	0.05553 (7)	0.0467 (4)
C5	0.72412 (18)	0.4313 (2)	0.01763 (6)	0.0471 (4)
C6	0.79271 (19)	0.5809 (2)	0.03449 (6)	0.0483 (4)
H6	0.8487	0.6387	0.0099	0.058*
C7	0.7392 (3)	0.3562 (3)	−0.03917 (7)	0.0707 (5)
H7A	0.7937	0.4320	−0.0608	0.106*
H7B	0.6349	0.3338	−0.0592	0.106*
H7C	0.7985	0.2550	−0.0338	0.106*
C8	0.4850 (3)	0.1124 (3)	0.07224 (11)	0.0960 (8)
H8A	0.5503	0.0867	0.1075	0.144*
H8B	0.4464	0.0117	0.0538	0.144*
H8C	0.3963	0.1789	0.0795	0.144*
C9	0.6813 (2)	0.6391 (2)	0.18320 (6)	0.0508 (4)
H9	0.7425	0.7423	0.1867	0.061*
C10	0.5123 (3)	0.6843 (4)	0.18816 (10)	0.0985 (9)
H10A	0.4737	0.7620	0.1589	0.148*
H10B	0.5078	0.7332	0.2246	0.148*
H10C	0.4472	0.5868	0.1841	0.148*
C11	0.7565 (4)	0.5276 (3)	0.22999 (9)	0.1153 (10)
H11A	0.6928	0.4298	0.2311	0.173*
H11B	0.7631	0.5845	0.2656	0.173*
H11C	0.8616	0.4973	0.2232	0.173*
C12	0.99177 (17)	0.80615 (17)	0.13445 (6)	0.0416 (3)
C13	1.05364 (17)	0.97651 (17)	0.14447 (6)	0.0402 (3)
C14	0.9796 (2)	1.11338 (19)	0.11761 (7)	0.0535 (4)
H14	0.8884	1.1002	0.0912	0.064*
C15	1.0407 (2)	1.2690 (2)	0.12988 (8)	0.0605 (5)
H15	0.9906	1.3607	0.1118	0.073*
C16	1.1752 (2)	1.2895 (2)	0.16867 (8)	0.0561 (4)
H16	1.2156	1.3950	0.1769	0.067*
C17	1.2503 (2)	1.1547 (2)	0.19528 (8)	0.0561 (4)
H17	1.3419	1.1688	0.2214	0.067*
C18	1.19010 (18)	0.99813 (19)	0.18335 (7)	0.0478 (4)
H18	1.2412	0.9069	0.2014	0.057*
O1	1.05685 (14)	0.68399 (13)	0.15440 (5)	0.0593 (3)
O2	0.85023 (13)	0.80333 (12)	0.10003 (5)	0.0495 (3)
O3	0.57625 (15)	0.20040 (15)	0.03683 (5)	0.0644 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0463 (8)	0.0325 (8)	0.0480 (8)	−0.0015 (6)	−0.0032 (7)	0.0000 (6)
C2	0.0447 (8)	0.0382 (8)	0.0449 (8)	0.0017 (6)	0.0021 (6)	−0.0034 (6)
C3	0.0504 (9)	0.0436 (9)	0.0490 (9)	−0.0072 (7)	0.0095 (7)	−0.0038 (7)
C4	0.0465 (8)	0.0400 (8)	0.0523 (9)	−0.0046 (7)	0.0025 (7)	−0.0093 (7)
C5	0.0486 (9)	0.0496 (9)	0.0416 (8)	−0.0003 (7)	0.0011 (7)	−0.0046 (7)
C6	0.0525 (9)	0.0475 (9)	0.0440 (8)	−0.0030 (7)	0.0035 (7)	0.0057 (7)
C7	0.0856 (14)	0.0759 (13)	0.0517 (10)	−0.0091 (11)	0.0138 (9)	−0.0162 (9)
C8	0.123 (2)	0.0693 (14)	0.1051 (17)	−0.0538 (14)	0.0470 (15)	−0.0320 (13)
C9	0.0592 (10)	0.0455 (9)	0.0476 (9)	−0.0051 (7)	0.0069 (7)	−0.0086 (7)
C10	0.0700 (13)	0.142 (2)	0.0866 (15)	−0.0023 (14)	0.0221 (12)	−0.0558 (16)
C11	0.199 (3)	0.0939 (18)	0.0466 (11)	0.0372 (19)	−0.0033 (15)	0.0001 (11)
C12	0.0446 (8)	0.0349 (8)	0.0449 (8)	0.0028 (6)	0.0046 (6)	0.0006 (6)
C13	0.0428 (8)	0.0335 (7)	0.0449 (8)	0.0013 (6)	0.0087 (6)	0.0001 (6)
C14	0.0505 (9)	0.0384 (9)	0.0673 (10)	−0.0001 (7)	−0.0062 (8)	0.0053 (8)
C15	0.0617 (11)	0.0332 (8)	0.0836 (13)	−0.0006 (7)	−0.0003 (9)	0.0082 (8)
C16	0.0568 (10)	0.0375 (9)	0.0741 (11)	−0.0090 (7)	0.0100 (9)	−0.0060 (8)
C17	0.0490 (9)	0.0526 (10)	0.0641 (10)	−0.0059 (8)	−0.0008 (8)	−0.0078 (8)
C18	0.0485 (9)	0.0405 (9)	0.0531 (9)	0.0044 (7)	0.0030 (7)	0.0015 (7)
O1	0.0596 (7)	0.0331 (6)	0.0803 (8)	0.0040 (5)	−0.0070 (6)	0.0040 (5)
O2	0.0540 (6)	0.0319 (5)	0.0583 (7)	−0.0037 (5)	−0.0064 (5)	0.0031 (5)
O3	0.0756 (8)	0.0526 (7)	0.0670 (8)	−0.0224 (6)	0.0165 (6)	−0.0217 (6)

Geometric parameters (Å, º) top

C1—C2	1.380 (2)	C9—H9	0.9800
C1—C6	1.380 (2)	C10—H10A	0.9600
C1—O2	1.4149 (17)	C10—H10B	0.9600
C2—C3	1.397 (2)	C10—H10C	0.9600
C2—C9	1.517 (2)	C11—H11A	0.9600
C3—C4	1.381 (2)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—O3	1.3685 (18)	C12—O1	1.1964 (17)
C4—C5	1.397 (2)	C12—O2	1.3531 (18)
C5—C6	1.378 (2)	C12—C13	1.481 (2)
C5—C7	1.504 (2)	C13—C14	1.384 (2)
C6—H6	0.9300	C13—C18	1.386 (2)
C7—H7A	0.9600	C14—C15	1.377 (2)
C7—H7B	0.9600	C14—H14	0.9300
C7—H7C	0.9600	C15—C16	1.371 (2)
C8—O3	1.415 (2)	C15—H15	0.9300
C8—H8A	0.9600	C16—C17	1.371 (2)
C8—H8B	0.9600	C16—H16	0.9300
C8—H8C	0.9600	C17—C18	1.379 (2)
C9—C10	1.500 (3)	C17—H17	0.9300
C9—C11	1.503 (3)	C18—H18	0.9300

C2—C1—C6	122.25 (14)	C9—C10—H10A	109.5
C2—C1—O2	120.49 (13)	C9—C10—H10B	109.5
C6—C1—O2	117.19 (13)	H10A—C10—H10B	109.5
C1—C2—C3	116.42 (14)	C9—C10—H10C	109.5
C1—C2—C9	122.90 (14)	H10A—C10—H10C	109.5
C3—C2—C9	120.68 (14)	H10B—C10—H10C	109.5
C4—C3—C2	121.77 (15)	C9—C11—H11A	109.5
C4—C3—H3	119.1	C9—C11—H11B	109.5
C2—C3—H3	119.1	H11A—C11—H11B	109.5
O3—C4—C3	124.36 (14)	C9—C11—H11C	109.5
O3—C4—C5	114.83 (13)	H11A—C11—H11C	109.5
C3—C4—C5	120.80 (14)	H11B—C11—H11C	109.5
C6—C5—C4	117.50 (14)	O1—C12—O2	123.04 (13)
C6—C5—C7	122.01 (15)	O1—C12—C13	124.86 (14)
C4—C5—C7	120.49 (15)	O2—C12—C13	112.10 (12)
C5—C6—C1	121.25 (14)	C14—C13—C18	119.23 (14)
C5—C6—H6	119.4	C14—C13—C12	122.88 (13)
C1—C6—H6	119.4	C18—C13—C12	117.88 (13)
C5—C7—H7A	109.5	C15—C14—C13	120.07 (15)
C5—C7—H7B	109.5	C15—C14—H14	120.0
H7A—C7—H7B	109.5	C13—C14—H14	120.0
C5—C7—H7C	109.5	C16—C15—C14	120.35 (16)
H7A—C7—H7C	109.5	C16—C15—H15	119.8
H7B—C7—H7C	109.5	C14—C15—H15	119.8
O3—C8—H8A	109.5	C15—C16—C17	120.11 (15)
O3—C8—H8B	109.5	C15—C16—H16	119.9
H8A—C8—H8B	109.5	C17—C16—H16	119.9
O3—C8—H8C	109.5	C16—C17—C18	120.07 (15)
H8A—C8—H8C	109.5	C16—C17—H17	120.0
H8B—C8—H8C	109.5	C18—C17—H17	120.0
C10—C9—C11	113.4 (2)	C17—C18—C13	120.16 (14)
C10—C9—C2	111.69 (14)	C17—C18—H18	119.9
C11—C9—C2	111.55 (15)	C13—C18—H18	119.9
C10—C9—H9	106.6	C12—O2—C1	117.16 (11)
C11—C9—H9	106.6	C4—O3—C8	118.13 (13)
C2—C9—H9	106.6

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀O₃
M_r	284.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.4765 (4), 8.0880 (4), 23.8119 (11)
β (°)	98.202 (2)
V (Å³)	1615.80 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.27 × 0.17 × 0.12

Data collection
Diffractometer	Bruker X8 APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14992, 2912, 2302
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.02
No. of reflections	2912
No. of parameters	194
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

The authors thank the CNRST and RéPAM for financial support and the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray diffraction measurements.

References

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