3-(4-Methoxy­phen­yl)isochroman-1-one

Hussain, M.T.; Tahir, M.N.; Adnan, A.; Hanif Ch, A.; Rama, N.H.

doi:10.1107/S1600536808032625

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2111

doi:10.1107/S1600536808032625

Open

access

3-(4-Methoxyphenyl)isochroman-1-one

Muhammad Tahir Hussain,^a M. Nawaz Tahir,^b ^* Ahmad Adnan,^c Asif Hanif Ch ^c and Nasim Hassan Rama ^d

^aDepartment of Chemistry, National Textile University, Faisalabad, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^cDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^dDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 27 September 2008; accepted 9 October 2008; online 15 October 2008)

In the molecule of the title compound, C₁₆H₁₄O₃, the aromatic rings are oriented at a dihedral angle of 72.02 (6)°. The heterocyclic ring adopts a twisted conformation. In the crystal structure, there are C—H⋯π contacts between the heterocyclic and phenyl rings, and between the methyl group and methoxyphenyl ring.

Related literature

For related structures, see: Schmalle et al. (1982 ); Schnebel et al. (2003 ). For bond-length data, see: Allen et al. (1987 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₆H₁₄O₃
M_r = 254.27
Monoclinic, P 2₁ /c
a = 11.8933 (7) Å
b = 14.6874 (9) Å
c = 7.4521 (4) Å
β = 101.040 (2)°
V = 1277.66 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.24 × 0.16 × 0.12 mm

Data collection

Bruker KappaAPEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.980, T_max = 0.996
12426 measured reflections
3302 independent reflections
2275 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.01
3302 reflections
175 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg2ⁱ	0.97	2.94	3.8398 (16)	154
C16—H16B⋯Cg3ⁱⁱ	0.96	2.89	3.7804 (17)	154
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); 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 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032625/hk2543sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032625/hk2543Isup2.hkl

checkCIF report

Comment top

The title compound was prepared in order to evalute its potential as antibacterial and antifungal agents. The CCDC search (Allen, 2002) showed that the crystal structures of rac-exo-tricarbonyl-(h6-3-phenylisochromanone)-chromium (Schnebel et al., 2003) and 3,4-dihydro-8-hydroxy-3-(4-hydroxyphenyl)-isocoumarin (Schmalle et al., 1982) have been reported, which have close resemblance as far as isochromane and attached phenyl ring is considered.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2–C7) and C (C10–C15) are, of course, planar, and they are oriented at a dihedral angle of 72.02 (6)°. Ring B (O2/C1/C2/C7–C9) is not planar, having total puckering amplitude, Q_T, of 0.483 (2) Å and twisted conformation [ϕ = 41.63 (3)° and θ = 116.64 (3)°] (Cremer & Pople, 1975).

In the crystal structure, there are C—H···π contacts (Table 1) between the heterocyclic and phenyl rings and the methyl group and methoxyphenyl ring, in which they may be effective in the stabilization of the structure.

Related literature top

For related structures, see: Schmalle et al. (1982); Schnebel et al. (2003). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

As shown in Fig. 3, a mixture of homophthalic acid, (1), (1.98 g, 11.0 mmol) and 4-methoxybenzoyl chloride, (2), (7.85 g, 46 mmol) was heated under reflux at 473 K. After concentration, the residue was chromatographed on silica gel column using petroleum ether (333–353 K) to give 3-(4-methoxyphenyl)isocoumarin, (3). 2-[2'-Oxoethyl-2'-(4'-methoxyphenyl)]benzoic acid, (4), was obtained by refluxing a solution of (3) (4 g, 15.9 mmol) in ethanol (200 ml) and potassium hydroxide (5%, 200 ml) for 4 h. NaBH₄ (1.6 g) was added to a solution of (4) (4.81 g, 17.8 mmol) in sodium hydroxide (1%, 180 ml) and the resulting solution was stirred overnight at room temperature. After being acidified with HCl, the whole mixture was extracted with dichloromethane (2 × 15 ml). Usual work-up gave crude racemic hydroxy-acid, (5), which was dissolved in acetic anhydride (5 ml) and heated under reflux for 2 h to get the title compound (6). The crude compound was purified by column chromatography on silica gel with petroleum ether and recrystallized in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound.
	Fig. 3. Preparation of the title compound.

3-(4-Methoxyphenyl)isochroman-1-one top

Crystal data top

C₁₆H₁₄O₃	F(000) = 536
M_r = 254.27	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3302 reflections
a = 11.8933 (7) Å	θ = 2.2–28.8°
b = 14.6874 (9) Å	µ = 0.09 mm⁻¹
c = 7.4521 (4) Å	T = 296 K
β = 101.040 (2)°	Prismatic, yellow
V = 1277.66 (13) Å³	0.24 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker KappaAPEXII CCD diffractometer	3302 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.8°, θ_min = 2.2°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→19
T_min = 0.980, T_max = 0.996	l = −9→10
12426 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0481P)² + 0.2427P] where P = (F_o² + 2F_c²)/3
3302 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₄O₃	V = 1277.66 (13) Å³
M_r = 254.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.8933 (7) Å	µ = 0.09 mm⁻¹
b = 14.6874 (9) Å	T = 296 K
c = 7.4521 (4) Å	0.24 × 0.16 × 0.12 mm
β = 101.040 (2)°

Data collection top

Bruker KappaAPEXII CCD diffractometer	3302 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2275 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.996	R_int = 0.023
12426 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.14 e Å⁻³
3302 reflections	Δρ_min = −0.22 e Å⁻³
175 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.56862 (10)	0.12610 (9)	−0.37797 (13)	0.0668 (4)
O2	0.68506 (8)	0.13694 (7)	−0.11396 (12)	0.0495 (3)
O3	1.15702 (8)	0.09384 (8)	0.43236 (15)	0.0642 (4)
C1	0.57829 (12)	0.13397 (9)	−0.21507 (18)	0.0460 (4)
C2	0.48087 (11)	0.13874 (8)	−0.11934 (17)	0.0421 (4)
C3	0.37156 (12)	0.15327 (9)	−0.2200 (2)	0.0512 (5)
C4	0.27961 (12)	0.15613 (10)	−0.1325 (2)	0.0575 (5)
C5	0.29633 (12)	0.14322 (10)	0.0534 (2)	0.0576 (5)
C6	0.40443 (12)	0.12764 (10)	0.1541 (2)	0.0519 (5)
C7	0.49834 (11)	0.12588 (8)	0.06918 (17)	0.0422 (4)
C8	0.61822 (11)	0.11135 (10)	0.17022 (17)	0.0465 (4)
C9	0.70140 (11)	0.16318 (9)	0.07877 (17)	0.0440 (4)
C10	0.82407 (11)	0.14481 (9)	0.16272 (17)	0.0438 (4)
C11	0.88770 (12)	0.20841 (10)	0.27598 (19)	0.0525 (5)
C12	0.99780 (12)	0.18919 (11)	0.3646 (2)	0.0573 (5)
C13	1.04728 (11)	0.10621 (10)	0.34024 (18)	0.0484 (4)
C14	0.98541 (12)	0.04249 (10)	0.2268 (2)	0.0542 (5)
C15	0.87482 (12)	0.06259 (10)	0.1397 (2)	0.0529 (5)
C16	1.20764 (14)	0.00719 (12)	0.4207 (2)	0.0664 (6)
H3	0.36043	0.16105	−0.34599	0.0615*
H4	0.20631	0.16679	−0.19903	0.0690*
H5	0.23396	0.14501	0.11186	0.0691*
H6	0.41438	0.11826	0.27955	0.0623*
H8A	0.62502	0.13197	0.29549	0.0558*
H8B	0.63641	0.04693	0.17237	0.0558*
H9	0.6859 (12)	0.2278 (10)	0.0814 (19)	0.0527*
H11	0.85577	0.26487	0.29252	0.0630*
H12	1.03908	0.23245	0.44148	0.0687*
H14	1.01772	−0.01364	0.20892	0.0651*
H15	0.83351	0.01922	0.06319	0.0635*
H16A	1.28412	0.00733	0.49143	0.0995*
H16B	1.16306	−0.03839	0.46749	0.0995*
H16C	1.21001	−0.00605	0.29534	0.0995*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0692 (7)	0.0953 (8)	0.0350 (5)	0.0026 (6)	0.0079 (5)	−0.0001 (5)
O2	0.0472 (5)	0.0654 (6)	0.0364 (5)	−0.0014 (4)	0.0096 (4)	0.0001 (4)
O3	0.0460 (6)	0.0818 (8)	0.0601 (6)	0.0054 (5)	−0.0018 (5)	−0.0082 (5)
C1	0.0519 (8)	0.0472 (7)	0.0378 (6)	0.0003 (6)	0.0062 (6)	0.0032 (5)
C2	0.0466 (7)	0.0375 (6)	0.0410 (7)	−0.0019 (5)	0.0057 (5)	0.0020 (5)
C3	0.0539 (8)	0.0477 (8)	0.0480 (8)	−0.0011 (6)	−0.0003 (6)	0.0040 (6)
C4	0.0443 (8)	0.0557 (8)	0.0688 (10)	0.0005 (6)	0.0013 (7)	0.0014 (7)
C5	0.0464 (8)	0.0594 (9)	0.0694 (10)	−0.0051 (6)	0.0170 (7)	−0.0047 (7)
C6	0.0513 (8)	0.0585 (8)	0.0477 (8)	−0.0056 (6)	0.0138 (6)	−0.0006 (6)
C7	0.0446 (7)	0.0408 (6)	0.0409 (7)	−0.0030 (5)	0.0072 (5)	0.0008 (5)
C8	0.0465 (7)	0.0574 (8)	0.0351 (6)	0.0001 (6)	0.0064 (5)	0.0041 (5)
C9	0.0465 (7)	0.0474 (7)	0.0375 (6)	−0.0012 (6)	0.0069 (5)	−0.0026 (5)
C10	0.0435 (7)	0.0493 (7)	0.0396 (6)	−0.0033 (5)	0.0106 (5)	−0.0023 (5)
C11	0.0501 (8)	0.0503 (8)	0.0565 (8)	−0.0003 (6)	0.0089 (6)	−0.0116 (6)
C12	0.0514 (8)	0.0615 (9)	0.0561 (9)	−0.0065 (7)	0.0033 (7)	−0.0168 (7)
C13	0.0416 (7)	0.0636 (9)	0.0401 (7)	−0.0007 (6)	0.0079 (5)	−0.0026 (6)
C14	0.0522 (8)	0.0547 (8)	0.0547 (8)	0.0056 (6)	0.0074 (7)	−0.0085 (7)
C15	0.0514 (8)	0.0522 (8)	0.0525 (8)	−0.0039 (6)	0.0033 (6)	−0.0126 (6)
C16	0.0561 (9)	0.0836 (12)	0.0574 (9)	0.0146 (8)	0.0060 (7)	0.0092 (8)

Geometric parameters (Å, º) top

O1—C1	1.2028 (16)	C12—C13	1.380 (2)
O2—C1	1.3475 (17)	C13—C14	1.376 (2)
O2—C9	1.4636 (15)	C14—C15	1.383 (2)
O3—C13	1.3655 (17)	C3—H3	0.9300
O3—C16	1.418 (2)	C4—H4	0.9300
C1—C2	1.4741 (19)	C5—H5	0.9300
C2—C3	1.387 (2)	C6—H6	0.9300
C2—C7	1.3931 (18)	C8—H8A	0.9700
C3—C4	1.377 (2)	C8—H8B	0.9700
C4—C5	1.375 (2)	C9—H9	0.968 (15)
C5—C6	1.378 (2)	C11—H11	0.9300
C6—C7	1.385 (2)	C12—H12	0.9300
C7—C8	1.4947 (19)	C14—H14	0.9300
C8—C9	1.5102 (19)	C15—H15	0.9300
C9—C10	1.4977 (19)	C16—H16A	0.9600
C10—C11	1.3831 (19)	C16—H16B	0.9600
C10—C15	1.375 (2)	C16—H16C	0.9600
C11—C12	1.378 (2)

O1···C16ⁱ	3.367 (2)	C16···H14	2.5100
O3···C4ⁱⁱ	3.4157 (18)	H3···O1	2.5800
O3···C3ⁱⁱ	3.3841 (18)	H3···O3^vi	2.8300
O1···H3	2.5800	H3···C5^iv	3.0300
O1···H6ⁱⁱⁱ	2.8500	H4···O3^vi	2.9000
O1···H9^iv	2.608 (15)	H5···O3^x	2.8200
O1···H8Aⁱⁱⁱ	2.6500	H5···C13^x	3.1000
O1···H16Aⁱ	2.8600	H6···O1^xi	2.8500
O2···H11^iv	2.6900	H6···H8A	2.4900
O2···H15	2.6400	H8A···O1^xi	2.6500
O2···H16Cⁱ	2.7800	H8A···H6	2.4900
O3···H3ⁱⁱ	2.8300	H8B···C15	2.9000
O3···H4ⁱⁱ	2.9000	H8B···C2^viii	3.0500
O3···H5^v	2.8200	H8B···C3^viii	2.9700
C3···C6^iv	3.395 (2)	H9···C2	2.915 (14)
C3···O3^vi	3.3841 (18)	H9···H11	2.3700
C3···C5^iv	3.465 (2)	H9···O1^vii	2.608 (15)
C4···O3^vi	3.4157 (18)	H9···C1^vii	2.967 (15)
C5···C3^vii	3.465 (2)	H11···H9	2.3700
C6···C3^vii	3.395 (2)	H11···O2^vii	2.6900
C16···O1ⁱ	3.367 (2)	H14···C16	2.5100
C1···H9^iv	2.967 (15)	H14···H16B	2.3600
C2···H8B^viii	3.0500	H14···H16C	2.2600
C2···H9	2.915 (14)	H15···O2	2.6400
C3···H16A^vi	3.0700	H15···C4^viii	3.0000
C3···H8B^viii	2.9700	H15···C5^viii	2.8800
C4···H15^viii	3.0000	H16A···C3ⁱⁱ	3.0700
C5···H3^vii	3.0300	H16A···O1ⁱ	2.8600
C5···H15^viii	2.8800	H16B···C14	2.7600
C13···H5^v	3.1000	H16B···H14	2.3600
C14···H16B	2.7600	H16B···C15^ix	3.0700
C14···H16C	2.7200	H16C···C14	2.7200
C15···H16B^ix	3.0700	H16C···H14	2.2600
C15···H8B	2.9000	H16C···O2ⁱ	2.7800

C1—O2—C9	119.41 (10)	C4—C3—H3	120.00
C13—O3—C16	117.70 (12)	C3—C4—H4	120.00
O1—C1—O2	117.72 (13)	C5—C4—H4	120.00
O1—C1—C2	124.12 (13)	C4—C5—H5	120.00
O2—C1—C2	118.15 (11)	C6—C5—H5	120.00
C1—C2—C3	119.19 (12)	C5—C6—H6	120.00
C1—C2—C7	120.16 (12)	C7—C6—H6	120.00
C3—C2—C7	120.63 (12)	C7—C8—H8A	110.00
C2—C3—C4	119.71 (13)	C7—C8—H8B	110.00
C3—C4—C5	119.89 (14)	C9—C8—H8A	110.00
C4—C5—C6	120.77 (14)	C9—C8—H8B	110.00
C5—C6—C7	120.27 (13)	H8A—C8—H8B	108.00
C2—C7—C6	118.72 (12)	O2—C9—H9	106.7 (8)
C2—C7—C8	118.10 (12)	C8—C9—H9	110.0 (9)
C6—C7—C8	123.18 (12)	C10—C9—H9	110.0 (9)
C7—C8—C9	110.17 (11)	C10—C11—H11	120.00
O2—C9—C8	109.56 (10)	C12—C11—H11	120.00
O2—C9—C10	107.35 (10)	C11—C12—H12	120.00
C8—C9—C10	112.99 (11)	C13—C12—H12	120.00
C9—C10—C11	120.57 (12)	C13—C14—H14	120.00
C9—C10—C15	121.45 (12)	C15—C14—H14	120.00
C11—C10—C15	117.85 (13)	C10—C15—H15	119.00
C10—C11—C12	120.85 (14)	C14—C15—H15	119.00
C11—C12—C13	120.51 (14)	O3—C16—H16A	109.00
O3—C13—C12	116.22 (13)	O3—C16—H16B	109.00
O3—C13—C14	124.44 (13)	O3—C16—H16C	109.00
C12—C13—C14	119.34 (13)	H16A—C16—H16B	109.00
C13—C14—C15	119.47 (13)	H16A—C16—H16C	109.00
C10—C15—C14	121.98 (13)	H16B—C16—H16C	109.00
C2—C3—H3	120.00

C9—O2—C1—O1	168.75 (13)	C5—C6—C7—C8	178.66 (13)
C9—O2—C1—C2	−12.42 (17)	C2—C7—C8—C9	32.06 (16)
C1—O2—C9—C8	47.27 (15)	C6—C7—C8—C9	−147.57 (13)
C1—O2—C9—C10	170.31 (11)	C7—C8—C9—O2	−55.05 (14)
C16—O3—C13—C12	175.67 (13)	C7—C8—C9—C10	−174.68 (11)
C16—O3—C13—C14	−4.8 (2)	O2—C9—C10—C11	134.82 (12)
O1—C1—C2—C3	−13.4 (2)	O2—C9—C10—C15	−49.38 (16)
O1—C1—C2—C7	164.54 (14)	C8—C9—C10—C11	−104.28 (15)
O2—C1—C2—C3	167.82 (12)	C8—C9—C10—C15	71.51 (16)
O2—C1—C2—C7	−14.21 (18)	C9—C10—C11—C12	175.05 (13)
C1—C2—C3—C4	178.77 (12)	C15—C10—C11—C12	−0.9 (2)
C7—C2—C3—C4	0.81 (19)	C9—C10—C15—C14	−175.39 (13)
C1—C2—C7—C6	−177.78 (12)	C11—C10—C15—C14	0.5 (2)
C1—C2—C7—C8	2.58 (17)	C10—C11—C12—C13	0.8 (2)
C3—C2—C7—C6	0.17 (18)	C11—C12—C13—O3	179.38 (13)
C3—C2—C7—C8	−179.48 (12)	C11—C12—C13—C14	−0.2 (2)
C2—C3—C4—C5	−1.0 (2)	O3—C13—C14—C15	−179.72 (13)
C3—C4—C5—C6	0.2 (2)	C12—C13—C14—C15	−0.2 (2)
C4—C5—C6—C7	0.8 (2)	C13—C14—C15—C10	0.0 (2)
C5—C6—C7—C2	−1.0 (2)

Symmetry codes: (i) −x+2, −y, −z; (ii) x+1, y, z+1; (iii) x, y, z−1; (iv) x, −y+1/2, z−1/2; (v) x+1, y, z; (vi) x−1, y, z−1; (vii) x, −y+1/2, z+1/2; (viii) −x+1, −y, −z; (ix) −x+2, −y, −z+1; (x) x−1, y, z; (xi) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg2^viii	0.97	2.94	3.8398 (16)	154
C16—H16B···Cg3^ix	0.96	2.89	3.7804 (17)	154

Symmetry codes: (viii) −x+1, −y, −z; (ix) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₃
M_r	254.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.8933 (7), 14.6874 (9), 7.4521 (4)
β (°)	101.040 (2)
V (Å³)	1277.66 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.16 × 0.12

Data collection
Diffractometer	Bruker KappaAPEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.980, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	12426, 3302, 2275
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.677

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.01
No. of reflections	3302
No. of parameters	175
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg2ⁱ	0.97	2.94	3.8398 (16)	154
C16—H16B···Cg3ⁱⁱ	0.96	2.89	3.7804 (17)	154

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

Acknowledgements

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Schmalle, H. W., Jarchow, O. H., Hausen, B. M. & Schulz, K.-H. (1982). Acta Cryst. B38, 2938–2941. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Schnebel, M., Weidner, I., Wartchow, R. & Butenschon, H. (2003). Eur. J. Org. Chem. pp. 4363–4372. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar