Methyl 3-(4-methoxy­benzo­yl)propionate

Ali, S.; Qadeer, G.; Rama, N.H.; Wong, W.-Y.

doi:10.1107/S1600536808037720

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2391

doi:10.1107/S1600536808037720

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Methyl 3-(4-methoxybenzoyl)propionate

Sajid Ali,^a Ghulam Qadeer,^a Nasim Hasan Rama ^a ^* and Wai-Yeung Wong ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong
^*Correspondence e-mail: nasimhrama@yahoo.com

(Received 7 November 2008; accepted 13 November 2008; online 20 November 2008)

The asymmetric unit of the title compound, C₁₂H₁₄O₃, contains two independent molecules, in which the benzene rings are oriented at a dihedral angle of 72.08 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. There are also C—H⋯π contacts between aromatic CH groups and the benzene rings.

Related literature

For general background, see: Hashem et al. (2007 ); Husain et al.(2005 ). For a related structure, see: Ali et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₄O₃
M_r = 206.23
Monoclinic, C 2/c
a = 34.762 (4) Å
b = 5.2861 (7) Å
c = 27.752 (3) Å
β = 117.182 (2)°
V = 4536.5 (9) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.28 × 0.26 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.798, T_max = 0.980
13099 measured reflections
5456 independent reflections
3364 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.174
S = 1.01
5456 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24A⋯O1ⁱ	0.96	2.53	3.467 (3)	164
C4—H4A⋯Cg1ⁱⁱ	0.93	3.17	3.858 (4)	133
C6—H6A⋯Cg2ⁱⁱⁱ	0.93	3.26	4.051 (3)	144
C18—H18A⋯Cg1	0.93	3.20	3.940 (3)	138
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) x, y-1, z. Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 rings.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037720/hk2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037720/hk2571Isup2.hkl

checkCIF report

Comment top

Benzoyl propionic acids and esters are important intermediates in heterocyclic chemistry and have been used for the synthesis of various biologically active five-membered heterocyles such as butenolides, pyrrolones (Husain et al., 2005), oxadiazoles and triazoles (Hashem et al., 2007). In view of the versatility of these compounds, we synthesized the title compound and reported herein its crystal structure.

The asymmetric unit of the title compound contains two crystallographically independent molecules of similar geometry (Fig.1). The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with the corresponding values in 3-(4-methoxybenzoyl)propionic acid (Ali et al., 2008). Rings A (C2-C7) and B (C14-C19) are, of course, planar and they are oriented at a dihedral angle of 72.08 (3)°.

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. There also exist C—H···π contacts (Table 1) between the aromatic CH groups and the benzene rings.

Related literature top

For general background, see: Hashem et al. (2007); Husain et al.(2005). For a related structure, see: Ali et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, the mixture of 3-(4-methoxybenzoyl) propionic acid (2.08 g, 10 mmol) and absolute methanol (50 ml) in the presence of a few drops of suphuric acid was refluxed for 5 h. The excess of solvent was removed by distillation. The solid residue for filltered off, washed with water and recystallized from ethanol (30%) to give the title compound. Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (yield; 83%, m.p. 308-309 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

Methyl 3-(4-methoxybenzoyl)propionate top

Crystal data top

C₁₂H₁₄O₃	F(000) = 1760
M_r = 206.23	D_x = 1.208 Mg m⁻³
Monoclinic, C2/c	Melting point: 308(1) K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 34.762 (4) Å	Cell parameters from 2335 reflections
b = 5.2861 (7) Å	θ = 5.3–18.6°
c = 27.752 (3) Å	µ = 0.09 mm⁻¹
β = 117.182 (2)°	T = 294 K
V = 4536.5 (9) Å³	Block, colorless
Z = 16	0.28 × 0.26 × 0.23 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5456 independent reflections
Radiation source: fine-focus sealed tube	3364 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −37→45
T_min = 0.798, T_max = 0.980	k = −6→6
13099 measured reflections	l = −37→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.0886P)² + 0.985P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
5456 reflections	Δρ_max = 0.25 e Å⁻³
272 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (4)

Crystal data top

C₁₂H₁₄O₃	V = 4536.5 (9) Å³
M_r = 206.23	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 34.762 (4) Å	µ = 0.09 mm⁻¹
b = 5.2861 (7) Å	T = 294 K
c = 27.752 (3) Å	0.28 × 0.26 × 0.23 mm
β = 117.182 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5456 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3364 reflections with I > 2σ(I)
T_min = 0.798, T_max = 0.980	R_int = 0.025
13099 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 1.01	Δρ_max = 0.25 e Å⁻³
5456 reflections	Δρ_min = −0.18 e Å⁻³
272 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.17237 (4)	0.1342 (3)	0.28466 (5)	0.0856 (4)
O2	0.07042 (4)	0.0750 (3)	0.24528 (5)	0.0908 (4)
O3	0.08802 (4)	−0.0612 (3)	0.32828 (5)	0.0849 (4)
O4	0.07570 (4)	0.7301 (3)	−0.03309 (5)	0.0848 (4)
O5	0.17800 (5)	0.7032 (3)	0.00217 (5)	0.0987 (5)
O6	0.16293 (5)	0.6067 (3)	−0.08206 (5)	0.0923 (5)
C1	0.23566 (7)	0.1919 (5)	0.09882 (8)	0.0915 (6)
H1A	0.2259	0.0684	0.0703	0.137*
H1B	0.2665	0.1819	0.1196	0.137*
H1C	0.2277	0.3579	0.0834	0.137*
C2	0.21493 (5)	0.1408 (3)	0.13526 (6)	0.0633 (4)
C3	0.22438 (5)	0.2949 (3)	0.17972 (6)	0.0633 (4)
H3A	0.2427	0.4326	0.1860	0.076*
C4	0.20724 (5)	0.2485 (3)	0.21467 (6)	0.0592 (4)
H4A	0.2144	0.3537	0.2444	0.071*
C5	0.17922 (4)	0.0452 (3)	0.20601 (6)	0.0527 (3)
C6	0.16911 (5)	−0.1061 (3)	0.16102 (6)	0.0622 (4)
H6A	0.1502	−0.2413	0.1541	0.075*
C7	0.18676 (6)	−0.0588 (3)	0.12648 (6)	0.0683 (4)
H7A	0.1796	−0.1633	0.0966	0.082*
C8	0.16253 (5)	−0.0046 (3)	0.24590 (6)	0.0584 (4)
C9	0.13441 (6)	−0.2324 (3)	0.23814 (7)	0.0695 (4)
H9A	0.1499	−0.3823	0.2367	0.083*
H9B	0.1087	−0.2176	0.2036	0.083*
C10	0.12090 (6)	−0.2663 (4)	0.28236 (8)	0.0749 (5)
H10A	0.1070	−0.4296	0.2779	0.090*
H10B	0.1465	−0.2659	0.3172	0.090*
C11	0.09074 (5)	−0.0647 (3)	0.28213 (7)	0.0645 (4)
C12	0.05918 (7)	0.1240 (5)	0.33221 (9)	0.0975 (7)
H12A	0.0597	0.1109	0.3670	0.146*
H12B	0.0303	0.0942	0.3043	0.146*
H12C	0.0683	0.2904	0.3280	0.146*
C13	0.01362 (6)	0.5636 (5)	0.15220 (8)	0.0921 (6)
H13A	−0.0064	0.7016	0.1435	0.138*
H13B	0.0360	0.5820	0.1887	0.138*
H13C	−0.0013	0.4068	0.1488	0.138*
C14	0.03334 (5)	0.5641 (3)	0.11394 (7)	0.0663 (4)
C15	0.02252 (6)	0.7474 (4)	0.07450 (7)	0.0760 (5)
H15A	0.0030	0.8735	0.0719	0.091*
C16	0.04011 (5)	0.7474 (3)	0.03875 (7)	0.0717 (5)
H16A	0.0321	0.8726	0.0124	0.086*
C17	0.06942 (5)	0.5640 (3)	0.04171 (6)	0.0572 (4)
C18	0.08110 (6)	0.3822 (3)	0.08218 (7)	0.0708 (5)
H18A	0.1011	0.2582	0.0855	0.085*
C19	0.06326 (6)	0.3842 (4)	0.11747 (7)	0.0750 (5)
H19A	0.0716	0.2612	0.1443	0.090*
C20	0.08610 (5)	0.5643 (3)	0.00094 (6)	0.0631 (4)
C21	0.11550 (6)	0.3537 (4)	0.00230 (8)	0.0770 (5)
H21A	0.1011	0.1937	−0.0001	0.092*
H21B	0.1413	0.3577	0.0369	0.092*
C22	0.12873 (7)	0.3661 (4)	−0.04260 (9)	0.0868 (6)
H22A	0.1424	0.2072	−0.0435	0.104*
H22B	0.1029	0.3841	−0.0769	0.104*
C23	0.15891 (6)	0.5766 (4)	−0.03702 (7)	0.0709 (5)
C24	0.19204 (7)	0.8028 (5)	−0.08167 (9)	0.1000 (7)
H24A	0.1923	0.8066	−0.1161	0.150*
H24B	0.2207	0.7686	−0.0536	0.150*
H24C	0.1825	0.9635	−0.0751	0.150*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1036 (9)	0.0928 (10)	0.0726 (8)	−0.0206 (8)	0.0509 (7)	−0.0246 (7)
O2	0.1021 (9)	0.1002 (11)	0.0765 (8)	0.0355 (8)	0.0462 (7)	0.0253 (7)
O3	0.0976 (9)	0.0987 (10)	0.0740 (8)	0.0180 (8)	0.0528 (7)	0.0146 (7)
O4	0.1052 (9)	0.0775 (9)	0.0786 (8)	0.0147 (7)	0.0478 (7)	0.0208 (7)
O5	0.1186 (11)	0.1140 (12)	0.0730 (8)	−0.0327 (9)	0.0522 (8)	−0.0226 (8)
O6	0.1053 (10)	0.1139 (12)	0.0700 (8)	−0.0022 (9)	0.0507 (7)	−0.0093 (8)
C1	0.0910 (13)	0.1117 (17)	0.0855 (13)	0.0006 (12)	0.0522 (11)	0.0034 (12)
C2	0.0589 (9)	0.0697 (10)	0.0598 (9)	0.0106 (7)	0.0259 (7)	0.0069 (8)
C3	0.0572 (8)	0.0606 (9)	0.0672 (9)	−0.0006 (7)	0.0242 (7)	0.0019 (8)
C4	0.0594 (8)	0.0547 (9)	0.0586 (8)	0.0005 (7)	0.0225 (7)	−0.0069 (7)
C5	0.0541 (7)	0.0487 (8)	0.0509 (7)	0.0080 (6)	0.0201 (6)	0.0019 (6)
C6	0.0713 (9)	0.0529 (9)	0.0595 (9)	−0.0035 (7)	0.0273 (7)	−0.0051 (7)
C7	0.0822 (10)	0.0653 (10)	0.0573 (9)	−0.0004 (8)	0.0316 (8)	−0.0091 (7)
C8	0.0605 (8)	0.0548 (9)	0.0576 (8)	0.0072 (7)	0.0249 (7)	−0.0006 (7)
C9	0.0812 (11)	0.0573 (10)	0.0812 (11)	0.0029 (8)	0.0466 (9)	−0.0008 (8)
C10	0.0902 (12)	0.0629 (10)	0.0844 (12)	0.0094 (9)	0.0510 (10)	0.0145 (9)
C11	0.0683 (9)	0.0653 (10)	0.0650 (9)	−0.0016 (8)	0.0348 (8)	0.0059 (8)
C12	0.1033 (15)	0.1157 (18)	0.0954 (15)	0.0148 (14)	0.0644 (13)	−0.0035 (13)
C13	0.0812 (12)	0.1145 (18)	0.0849 (13)	−0.0088 (12)	0.0416 (10)	0.0061 (12)
C14	0.0616 (9)	0.0695 (11)	0.0609 (9)	−0.0118 (8)	0.0219 (7)	−0.0007 (8)
C15	0.0741 (10)	0.0726 (12)	0.0813 (12)	0.0137 (9)	0.0355 (9)	0.0095 (9)
C16	0.0768 (10)	0.0646 (11)	0.0719 (10)	0.0135 (8)	0.0324 (9)	0.0178 (8)
C17	0.0585 (8)	0.0463 (8)	0.0573 (8)	−0.0045 (6)	0.0182 (7)	0.0001 (6)
C18	0.0784 (10)	0.0547 (9)	0.0737 (11)	0.0096 (8)	0.0301 (9)	0.0094 (8)
C19	0.0878 (12)	0.0652 (11)	0.0684 (10)	0.0022 (9)	0.0324 (9)	0.0167 (8)
C20	0.0691 (9)	0.0529 (9)	0.0616 (9)	−0.0059 (7)	0.0250 (7)	−0.0015 (7)
C21	0.0949 (12)	0.0555 (10)	0.0905 (13)	0.0031 (9)	0.0510 (11)	0.0012 (9)
C22	0.1103 (14)	0.0699 (12)	0.0914 (13)	−0.0015 (11)	0.0560 (12)	−0.0178 (10)
C23	0.0805 (11)	0.0753 (12)	0.0622 (10)	0.0100 (9)	0.0372 (9)	−0.0041 (8)
C24	0.1055 (15)	0.1219 (19)	0.0944 (15)	0.0072 (14)	0.0645 (13)	0.0115 (14)

Geometric parameters (Å, º) top

C1—C2	1.510 (2)	C13—C14	1.504 (2)
C1—H1A	0.9600	C13—H13A	0.9600
C1—H1B	0.9600	C13—H13B	0.9600
C1—H1C	0.9600	C13—H13C	0.9600
C2—C7	1.384 (2)	C14—C15	1.379 (2)
C2—C3	1.387 (2)	C14—C19	1.379 (2)
C3—C4	1.373 (2)	C15—C16	1.383 (2)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.396 (2)	C16—C17	1.382 (2)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.386 (2)	C17—C18	1.390 (2)
C5—C8	1.489 (2)	C17—C20	1.489 (2)
C6—C7	1.377 (2)	C18—C19	1.378 (2)
C6—H6A	0.9300	C18—H18A	0.9300
C7—H7A	0.9300	C19—H19A	0.9300
C8—O1	1.2151 (19)	C20—O4	1.2159 (19)
C8—C9	1.503 (2)	C20—C21	1.500 (2)
C9—C10	1.511 (2)	C21—C22	1.514 (3)
C9—H9A	0.9700	C21—H21A	0.9700
C9—H9B	0.9700	C21—H21B	0.9700
C10—C11	1.493 (2)	C22—C23	1.488 (3)
C10—H10A	0.9700	C22—H22A	0.9700
C10—H10B	0.9700	C22—H22B	0.9700
C11—O2	1.1955 (19)	C23—O5	1.188 (2)
C11—O3	1.3268 (19)	C23—O6	1.329 (2)
C12—O3	1.440 (2)	C24—O6	1.445 (3)
C12—H12A	0.9600	C24—H24A	0.9600
C12—H12B	0.9600	C24—H24B	0.9600
C12—H12C	0.9600	C24—H24C	0.9600

C2—C1—H1A	109.5	C14—C13—H13B	109.5
C2—C1—H1B	109.5	H13A—C13—H13B	109.5
H1A—C1—H1B	109.5	C14—C13—H13C	109.5
C2—C1—H1C	109.5	H13A—C13—H13C	109.5
H1A—C1—H1C	109.5	H13B—C13—H13C	109.5
H1B—C1—H1C	109.5	C15—C14—C19	117.67 (16)
C7—C2—C3	117.74 (15)	C15—C14—C13	120.96 (17)
C7—C2—C1	122.31 (17)	C19—C14—C13	121.37 (17)
C3—C2—C1	119.94 (17)	C14—C15—C16	121.32 (17)
C4—C3—C2	121.40 (15)	C14—C15—H15A	119.3
C4—C3—H3A	119.3	C16—C15—H15A	119.3
C2—C3—H3A	119.3	C17—C16—C15	120.85 (16)
C3—C4—C5	120.66 (14)	C17—C16—H16A	119.6
C3—C4—H4A	119.7	C15—C16—H16A	119.6
C5—C4—H4A	119.7	C16—C17—C18	117.93 (15)
C6—C5—C4	117.99 (14)	C16—C17—C20	119.12 (14)
C6—C5—C8	122.87 (14)	C18—C17—C20	122.93 (15)
C4—C5—C8	119.11 (13)	C19—C18—C17	120.59 (16)
C7—C6—C5	120.80 (15)	C19—C18—H18A	119.7
C7—C6—H6A	119.6	C17—C18—H18A	119.7
C5—C6—H6A	119.6	C18—C19—C14	121.61 (16)
C6—C7—C2	121.38 (15)	C18—C19—H19A	119.2
C6—C7—H7A	119.3	C14—C19—H19A	119.2
C2—C7—H7A	119.3	O4—C20—C17	120.69 (15)
O1—C8—C5	120.22 (15)	O4—C20—C21	120.79 (16)
O1—C8—C9	120.82 (15)	C17—C20—C21	118.51 (14)
C5—C8—C9	118.94 (13)	C20—C21—C22	114.01 (16)
C8—C9—C10	113.66 (15)	C20—C21—H21A	108.7
C8—C9—H9A	108.8	C22—C21—H21A	108.7
C10—C9—H9A	108.8	C20—C21—H21B	108.7
C8—C9—H9B	108.8	C22—C21—H21B	108.7
C10—C9—H9B	108.8	H21A—C21—H21B	107.6
H9A—C9—H9B	107.7	C23—C22—C21	114.28 (16)
C11—C10—C9	112.96 (14)	C23—C22—H22A	108.7
C11—C10—H10A	109.0	C21—C22—H22A	108.7
C9—C10—H10A	109.0	C23—C22—H22B	108.7
C11—C10—H10B	109.0	C21—C22—H22B	108.7
C9—C10—H10B	109.0	H22A—C22—H22B	107.6
H10A—C10—H10B	107.8	O5—C23—O6	122.60 (19)
O2—C11—O3	122.84 (16)	O5—C23—C22	126.08 (17)
O2—C11—C10	125.71 (16)	O6—C23—C22	111.31 (16)
O3—C11—C10	111.44 (14)	O6—C24—H24A	109.5
O3—C12—H12A	109.5	O6—C24—H24B	109.5
O3—C12—H12B	109.5	H24A—C24—H24B	109.5
H12A—C12—H12B	109.5	O6—C24—H24C	109.5
O3—C12—H12C	109.5	H24A—C24—H24C	109.5
H12A—C12—H12C	109.5	H24B—C24—H24C	109.5
H12B—C12—H12C	109.5	C11—O3—C12	116.21 (15)
C14—C13—H13A	109.5	C23—O6—C24	116.92 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···O1ⁱ	0.96	2.53	3.467 (3)	164
C4—H4A···Cg1ⁱⁱ	0.93	3.17	3.858 (4)	133
C6—H6A···Cg2ⁱⁱⁱ	0.93	3.26	4.051 (3)	144
C18—H18A···Cg1	0.93	3.20	3.940 (3)	138

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y, z−1/2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄O₃
M_r	206.23
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	34.762 (4), 5.2861 (7), 27.752 (3)
β (°)	117.182 (2)
V (Å³)	4536.5 (9)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.26 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.798, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	13099, 5456, 3364
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.174, 1.01
No. of reflections	5456
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···O1ⁱ	0.96	2.53	3.467 (3)	164
C4—H4A···Cg1ⁱⁱ	0.93	3.17	3.858 (4)	133
C6—H6A···Cg2ⁱⁱⁱ	0.93	3.26	4.051 (3)	144
C18—H18A···Cg1	0.93	3.20	3.940 (3)	138

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y, z−1/2; (iii) x, y−1, z.

Acknowledgements

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

References

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