5-(Biphenyl-4-yl)-3-(3-meth­oxy­benzyl­idene)furan-2(3H)-one

Jasinski, J.P.; Golen, J.A.; Dayananda, A.S.; Yathirajan, H.S.; Mishra, R.

doi:10.1107/S1600536811031588

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2294-o2295

doi:10.1107/S1600536811031588

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5-(Biphenyl-4-yl)-3-(3-methoxybenzylidene)furan-2(3H)-one

Jerry P. Jasinski,^a ^* James A. Golen,^a A. S. Dayananda,^b H. S. Yathirajan ^b and Ravinesh Mishra ^c

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard (Hamdard University), Hamdard Nagar, New Delhi 110 062, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 2 August 2011; accepted 4 August 2011; online 11 August 2011)

In the title compound, C₂₄H₁₈O₃, the dihedral angles between the mean planes of the five-membered furan ring and the methoxy-substituted benzene and the adjacent and outer biphenyl benzene rings are 2.43 (7), 4.48 (7) and 30.47 (8)°, respectively. The crystal packing is stabilized by weak C—H⋯O and C—H⋯π intermolecular hydrogen bonds and π–π stacking interactions [centroid–centroid distances = 3.8752 (8) and 3.8331 (8) Å].

Related literature

For potential anti-ulcer agents containing a furanone structure, see: Felman et al. (1992 ). For the role of furanones in the biochemical processes of the human body, see: Rappai et al. (2009 ). For the gastrointestinal toxicity of acidic non-steroidal anti-inflammatory drugs (NSAIDs), see: Husain et al. (2010 ). For gastrointestinal side effects of NSAIDS, see: Cioli et al. (1979 ). For biologically active five-membered heterocyles such as butenolides and pyrrolones, see: Husain et al. (2005 ); Khan & Husain (2002 ). For oxadiazoles and triazoles, see: Husain & Ajmal (2009 ); Hashem et al. (2007 ). For a related structure, see: Burke et al. (2000 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₁₈O₃
M_r = 354.38
Monoclinic, P 2₁ /c
a = 19.8766 (8) Å
b = 6.9914 (3) Å
c = 13.2603 (6) Å
β = 107.735 (4)°
V = 1755.15 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 170 K
0.22 × 0.22 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.981, T_max = 0.990
19756 measured reflections
4534 independent reflections
3310 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.143
S = 1.01
4534 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3ⁱ	0.95	2.56	3.3358 (18)	138
C5—H5A⋯Cg1ⁱⁱ	0.95	2.69	3.4762 (16)	141
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031588/ci5197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031588/ci5197Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031588/ci5197Isup3.cml

checkCIF report

Comment top

Certain drugs containing a furanone structure were potential anti-ulcer agents because they did not irritate the lining of the stomach (Felman et al., 1992). Their occurrence in nature has been exploited in the pharmaceutical industry because of their unusual biological activities, such as anti-ulcer and anti-cancer treatments. The antitumor activity of several analogs of furanones was evaluated using both in vivo and in vitro methods on mice, where oral adminstration showed a relative decrease in tumor growth. In an effort to create more efficient drugs, scientists began to explore the role of furanones in the biochemical processes of the human body (Rappai et al., 2009). The gastrointestinal toxicity of acidic non-steroidal anti- inflammatory drugs (NSAIDs) is one of the most challenging problems in medicinal chemistry (Husain et al., 2010). NSAIDs form a class of therapeutic agents that are most widely used world over because of their antiinflammatory, analgesic and antipyretic effects. Aroylpropionic acids and furanones are effective anti-inflammatory agents and some of them are available in the market, however, they are associated with gastrointestinal side effects; a common feature of NSAIDs (Cioli et al., 1979). Studies suggest that the direct tissue contact of these agents plays an important role in the production of side effects and the reported literature confirms that gastrointestinal side effects of aroylpropionic acids are due to the presence of the free carboxylic group in the parent drug. This free carboxylic group, therefore, has been converted to the furanone ring to get a compound free from GIT side effects. Furanones and b\-aroylpropionic acids 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; Khan et al., 2002) oxadiazoles (Husain et al., 2009) and triazoles (Hashem et al., 2007). The crystal structure study of a related compound, (E)-6-methoxy-3-( -methoxybenzylidene)benzo[b]furan-2(3H)-one, at 173 K is reported (Burke et al., 2000). In view of the importance of the title compound, (I), this paper reports its crystal structure.

In the title molecule, the dihedral angles between the mean planes of the five-menbered furan ring and the methoxy substituted benzene and biphenyl benzene rings are 2.43 (7)°, 4.48 (7)°, and 30.47 (8)°, respectively (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). The crystal packing is stabiized by weak C—H···O and C—H···π intermolecular hydrogen bonds and π-π stacking (Table 2) interactions (Fig. 2).

Related literature top

For potential anti-ulcer agents containing a furanone structure, see: Felman et al. (1992). For the role of furanones in the biochemical processes of the human body, see: Rappai et al. (2009). For the gastrointestinal toxicity of acidic non-steroidal anti-inflammatory drugs (NSAIDs), see: Husain et al. (2010). For gastrointestinal side effects of NSAIDS, see: Cioli et al. (1979). For biologically active five-membered heterocyles such as butenolides and pyrrolones, see: Husain et al. (2005); Khan & Husain (2002). For oxadiazoles and triazoles, see: Husain & Ajmal (2009); Hashem et al. (2007). For a related structure, see: Burke et al. (2000). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of 3-(4-phenylbenzoyl)propionic acid (0.71 g, 3 mmol) and 3-methoxybenzaldehyde (0.45 g, 3 mmol) in a acetic anhydride (5 ml) with triethylamine (3–4 drops) was refluxed for 5–6 hrs on a water bath under anhydrous conditions. After completion of the reaction, the contents were poured into crushed ice in small portions while stirring. A solid mass separated out, which was filtered, washed with water and crystallized from 2-butanone to get X-ray quality crystals (m.p. 411–413 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, viewed down the b axis.

5-(Biphenyl-4-yl)-3-(3-methoxybenzylidene)furan-2(3H)-one top

Crystal data top

C₂₄H₁₈O₃	F(000) = 744
M_r = 354.38	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5822 reflections
a = 19.8766 (8) Å	θ = 3.1–32.2°
b = 6.9914 (3) Å	µ = 0.09 mm⁻¹
c = 13.2603 (6) Å	T = 170 K
β = 107.735 (4)°	Block, pale yellow
V = 1755.15 (13) Å³	0.22 × 0.22 × 0.12 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4534 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 16.1500 pixels mm^-1	θ_max = 28.7°, θ_min = 3.2°
ω scans	h = −26→26
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −9→9
T_min = 0.981, T_max = 0.990	l = −17→17
19756 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0722P)² + 0.299P] where P = (F_o² + 2F_c²)/3
4534 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₄H₁₈O₃	V = 1755.15 (13) Å³
M_r = 354.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.8766 (8) Å	µ = 0.09 mm⁻¹
b = 6.9914 (3) Å	T = 170 K
c = 13.2603 (6) Å	0.22 × 0.22 × 0.12 mm
β = 107.735 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4534 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	3310 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.990	R_int = 0.029
19756 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
4534 reflections	Δρ_min = −0.16 e Å⁻³
245 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	0.71593 (5)	0.14726 (16)	0.22178 (7)	0.0415 (3)
O2	0.63009 (6)	0.13953 (19)	0.06638 (8)	0.0539 (3)
O3	0.28081 (5)	0.15321 (18)	0.15671 (9)	0.0516 (3)
C1	1.04917 (7)	0.3141 (2)	0.59764 (12)	0.0393 (3)
H1A	1.0398	0.3604	0.5274	0.047*
C2	1.11564 (8)	0.3377 (2)	0.66876 (14)	0.0470 (4)
H2A	1.1514	0.4004	0.6473	0.056*
C3	1.13016 (8)	0.2703 (3)	0.77084 (13)	0.0497 (4)
H3A	1.1759	0.2862	0.8199	0.060*
C4	1.07787 (9)	0.1797 (3)	0.80145 (13)	0.0500 (4)
H4A	1.0879	0.1325	0.8717	0.060*
C5	1.01101 (8)	0.1571 (2)	0.73078 (12)	0.0411 (3)
H5A	0.9753	0.0958	0.7531	0.049*
C6	0.99552 (7)	0.2235 (2)	0.62704 (11)	0.0330 (3)
C7	0.92411 (7)	0.19992 (19)	0.55035 (10)	0.0317 (3)
C8	0.86347 (7)	0.2076 (2)	0.58311 (11)	0.0395 (3)
H8A	0.8685	0.2235	0.6562	0.047*
C9	0.79673 (7)	0.1927 (2)	0.51171 (11)	0.0389 (3)
H9A	0.7565	0.1986	0.5361	0.047*
C10	0.78789 (7)	0.16882 (19)	0.40409 (10)	0.0315 (3)
C11	0.84804 (7)	0.1561 (2)	0.37113 (11)	0.0365 (3)
H11A	0.8431	0.1359	0.2984	0.044*
C12	0.91467 (7)	0.1724 (2)	0.44324 (11)	0.0363 (3)
H12A	0.9549	0.1646	0.4190	0.044*
C13	0.71770 (7)	0.1588 (2)	0.32790 (10)	0.0329 (3)
C14	0.65258 (7)	0.16084 (19)	0.33828 (10)	0.0331 (3)
H14A	0.6416	0.1683	0.4030	0.040*
C15	0.60244 (7)	0.14966 (19)	0.23409 (10)	0.0322 (3)
C16	0.64589 (7)	0.1442 (2)	0.16115 (11)	0.0379 (3)
C17	0.53146 (7)	0.1432 (2)	0.19272 (10)	0.0340 (3)
H17A	0.5149	0.1351	0.1177	0.041*
C18	0.47600 (7)	0.14655 (19)	0.24314 (10)	0.0318 (3)
C19	0.40626 (7)	0.1452 (2)	0.17584 (11)	0.0340 (3)
H19A	0.3975	0.1408	0.1013	0.041*
C20	0.35005 (7)	0.1504 (2)	0.21690 (11)	0.0363 (3)
C21	0.36229 (8)	0.1503 (2)	0.32559 (12)	0.0418 (4)
H21A	0.3238	0.1504	0.3540	0.050*
C22	0.43071 (8)	0.1501 (2)	0.39204 (12)	0.0436 (4)
H22A	0.4390	0.1498	0.4665	0.052*
C23	0.48761 (7)	0.1505 (2)	0.35246 (11)	0.0383 (3)
H23A	0.5344	0.1534	0.3995	0.046*
C24	0.26584 (9)	0.1751 (3)	0.04562 (13)	0.0543 (4)
H24A	0.2147	0.1852	0.0125	0.081*
H24B	0.2838	0.0640	0.0168	0.081*
H24C	0.2888	0.2913	0.0309	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0317 (5)	0.0641 (7)	0.0309 (5)	0.0013 (5)	0.0128 (4)	0.0002 (4)
O2	0.0438 (6)	0.0898 (9)	0.0293 (5)	0.0029 (6)	0.0128 (5)	0.0027 (5)
O3	0.0273 (5)	0.0822 (9)	0.0436 (6)	0.0008 (5)	0.0084 (4)	0.0029 (6)
C1	0.0339 (7)	0.0437 (8)	0.0425 (8)	0.0023 (6)	0.0150 (6)	0.0029 (6)
C2	0.0317 (7)	0.0508 (9)	0.0608 (10)	−0.0004 (6)	0.0174 (7)	−0.0006 (8)
C3	0.0302 (7)	0.0584 (10)	0.0535 (10)	0.0033 (7)	0.0026 (7)	−0.0021 (8)
C4	0.0437 (8)	0.0595 (11)	0.0415 (8)	0.0041 (7)	0.0048 (7)	0.0051 (7)
C5	0.0378 (7)	0.0458 (9)	0.0401 (8)	−0.0024 (6)	0.0121 (6)	0.0039 (6)
C6	0.0296 (6)	0.0338 (7)	0.0364 (7)	0.0029 (5)	0.0110 (5)	−0.0006 (5)
C7	0.0293 (6)	0.0323 (7)	0.0342 (7)	0.0012 (5)	0.0110 (5)	0.0009 (5)
C8	0.0340 (7)	0.0550 (9)	0.0312 (7)	−0.0010 (6)	0.0125 (6)	−0.0033 (6)
C9	0.0300 (7)	0.0542 (9)	0.0360 (7)	−0.0004 (6)	0.0150 (6)	−0.0035 (6)
C10	0.0298 (6)	0.0325 (7)	0.0334 (7)	0.0005 (5)	0.0114 (5)	0.0007 (5)
C11	0.0362 (7)	0.0453 (8)	0.0301 (7)	0.0011 (6)	0.0133 (5)	−0.0012 (6)
C12	0.0305 (6)	0.0445 (8)	0.0379 (7)	0.0015 (6)	0.0166 (6)	−0.0010 (6)
C13	0.0343 (7)	0.0370 (7)	0.0281 (6)	0.0008 (5)	0.0106 (5)	−0.0007 (5)
C14	0.0305 (6)	0.0393 (7)	0.0302 (7)	0.0004 (5)	0.0102 (5)	−0.0002 (5)
C15	0.0334 (7)	0.0345 (7)	0.0298 (6)	0.0028 (5)	0.0115 (5)	0.0018 (5)
C16	0.0333 (7)	0.0504 (9)	0.0307 (7)	0.0027 (6)	0.0108 (6)	0.0024 (6)
C17	0.0328 (7)	0.0409 (8)	0.0279 (6)	0.0027 (6)	0.0088 (5)	0.0030 (5)
C18	0.0311 (6)	0.0332 (7)	0.0310 (6)	0.0011 (5)	0.0091 (5)	0.0005 (5)
C19	0.0327 (7)	0.0397 (8)	0.0289 (6)	0.0001 (5)	0.0085 (5)	−0.0001 (5)
C20	0.0294 (6)	0.0403 (8)	0.0379 (7)	−0.0007 (5)	0.0086 (6)	−0.0009 (6)
C21	0.0375 (7)	0.0530 (9)	0.0401 (8)	0.0002 (6)	0.0196 (6)	−0.0016 (7)
C22	0.0454 (8)	0.0560 (10)	0.0309 (7)	0.0006 (7)	0.0140 (6)	−0.0016 (6)
C23	0.0323 (7)	0.0486 (8)	0.0320 (7)	0.0003 (6)	0.0067 (5)	0.0003 (6)
C24	0.0369 (8)	0.0779 (13)	0.0418 (9)	0.0006 (8)	0.0027 (7)	−0.0008 (8)

Geometric parameters (Å, º) top

O1—C16	1.3795 (16)	C10—C13	1.4537 (18)
O1—C13	1.3991 (15)	C11—C12	1.3819 (19)
O2—C16	1.1994 (16)	C11—H11A	0.95
O3—C20	1.3647 (16)	C12—H12A	0.95
O3—C24	1.4195 (19)	C13—C14	1.3427 (18)
C1—C2	1.379 (2)	C14—C15	1.4385 (18)
C1—C6	1.3941 (19)	C14—H14A	0.95
C1—H1A	0.95	C15—C17	1.3499 (18)
C2—C3	1.378 (2)	C15—C16	1.4803 (19)
C2—H2A	0.95	C17—C18	1.4531 (18)
C3—C4	1.380 (2)	C17—H17A	0.95
C3—H3A	0.95	C18—C23	1.3971 (19)
C4—C5	1.382 (2)	C18—C19	1.4016 (18)
C4—H4A	0.95	C19—C20	1.3845 (19)
C5—C6	1.3945 (19)	C19—H19A	0.95
C5—H5A	0.95	C20—C21	1.387 (2)
C6—C7	1.4821 (18)	C21—C22	1.377 (2)
C7—C12	1.3882 (18)	C21—H21A	0.95
C7—C8	1.4010 (18)	C22—C23	1.384 (2)
C8—C9	1.3792 (19)	C22—H22A	0.95
C8—H8A	0.95	C23—H23A	0.95
C9—C10	1.3937 (19)	C24—H24A	0.98
C9—H9A	0.95	C24—H24B	0.98
C10—C11	1.3954 (18)	C24—H24C	0.98

C16—O1—C13	107.39 (10)	C14—C13—C10	132.78 (12)
C20—O3—C24	117.63 (12)	O1—C13—C10	115.25 (11)
C2—C1—C6	121.21 (14)	C13—C14—C15	107.96 (12)
C2—C1—H1A	119.4	C13—C14—H14A	126.0
C6—C1—H1A	119.4	C15—C14—H14A	126.0
C3—C2—C1	120.07 (15)	C17—C15—C14	136.44 (13)
C3—C2—H2A	120.0	C17—C15—C16	118.63 (12)
C1—C2—H2A	120.0	C14—C15—C16	104.92 (11)
C2—C3—C4	119.65 (14)	O2—C16—O1	120.44 (12)
C2—C3—H3A	120.2	O2—C16—C15	131.81 (13)
C4—C3—H3A	120.2	O1—C16—C15	107.74 (11)
C3—C4—C5	120.52 (15)	C15—C17—C18	131.15 (13)
C3—C4—H4A	119.7	C15—C17—H17A	114.4
C5—C4—H4A	119.7	C18—C17—H17A	114.4
C4—C5—C6	120.57 (14)	C23—C18—C19	118.66 (12)
C4—C5—H5A	119.7	C23—C18—C17	124.69 (12)
C6—C5—H5A	119.7	C19—C18—C17	116.66 (12)
C1—C6—C5	117.98 (12)	C20—C19—C18	120.63 (12)
C1—C6—C7	120.87 (12)	C20—C19—H19A	119.7
C5—C6—C7	121.16 (12)	C18—C19—H19A	119.7
C12—C7—C8	117.49 (12)	O3—C20—C19	124.14 (13)
C12—C7—C6	121.34 (12)	O3—C20—C21	115.74 (12)
C8—C7—C6	121.16 (12)	C19—C20—C21	120.11 (13)
C9—C8—C7	121.52 (13)	C22—C21—C20	119.45 (13)
C9—C8—H8A	119.2	C22—C21—H21A	120.3
C7—C8—H8A	119.2	C20—C21—H21A	120.3
C8—C9—C10	120.45 (13)	C21—C22—C23	121.27 (13)
C8—C9—H9A	119.8	C21—C22—H22A	119.4
C10—C9—H9A	119.8	C23—C22—H22A	119.4
C9—C10—C11	118.40 (12)	C22—C23—C18	119.84 (13)
C9—C10—C13	120.82 (12)	C22—C23—H23A	120.1
C11—C10—C13	120.78 (12)	C18—C23—H23A	120.1
C12—C11—C10	120.66 (13)	O3—C24—H24A	109.5
C12—C11—H11A	119.7	O3—C24—H24B	109.5
C10—C11—H11A	119.7	H24A—C24—H24B	109.5
C11—C12—C7	121.45 (12)	O3—C24—H24C	109.5
C11—C12—H12A	119.3	H24A—C24—H24C	109.5
C7—C12—H12A	119.3	H24B—C24—H24C	109.5
C14—C13—O1	111.96 (11)

C6—C1—C2—C3	0.4 (2)	C11—C10—C13—O1	−3.56 (19)
C1—C2—C3—C4	−0.1 (3)	O1—C13—C14—C15	0.14 (16)
C2—C3—C4—C5	−0.4 (3)	C10—C13—C14—C15	179.15 (14)
C3—C4—C5—C6	0.7 (2)	C13—C14—C15—C17	178.84 (16)
C2—C1—C6—C5	0.0 (2)	C13—C14—C15—C16	−0.94 (15)
C2—C1—C6—C7	179.58 (13)	C13—O1—C16—O2	178.09 (14)
C4—C5—C6—C1	−0.5 (2)	C13—O1—C16—C15	−1.35 (15)
C4—C5—C6—C7	179.88 (14)	C17—C15—C16—O2	2.2 (2)
C1—C6—C7—C12	33.2 (2)	C14—C15—C16—O2	−177.94 (17)
C5—C6—C7—C12	−147.21 (15)	C17—C15—C16—O1	−178.42 (12)
C1—C6—C7—C8	−145.78 (15)	C14—C15—C16—O1	1.42 (15)
C5—C6—C7—C8	33.8 (2)	C14—C15—C17—C18	0.4 (3)
C12—C7—C8—C9	−1.4 (2)	C16—C15—C17—C18	−179.83 (13)
C6—C7—C8—C9	177.64 (13)	C15—C17—C18—C23	−2.6 (2)
C7—C8—C9—C10	0.2 (2)	C15—C17—C18—C19	177.53 (14)
C8—C9—C10—C11	1.5 (2)	C23—C18—C19—C20	0.9 (2)
C8—C9—C10—C13	−178.10 (13)	C17—C18—C19—C20	−179.26 (13)
C9—C10—C11—C12	−1.9 (2)	C24—O3—C20—C19	−7.8 (2)
C13—C10—C11—C12	177.69 (13)	C24—O3—C20—C21	173.06 (14)
C10—C11—C12—C7	0.7 (2)	C18—C19—C20—O3	178.70 (13)
C8—C7—C12—C11	1.0 (2)	C18—C19—C20—C21	−2.2 (2)
C6—C7—C12—C11	−178.05 (13)	O3—C20—C21—C22	−179.16 (13)
C16—O1—C13—C14	0.79 (16)	C19—C20—C21—C22	1.7 (2)
C16—O1—C13—C10	−178.41 (11)	C20—C21—C22—C23	0.2 (2)
C9—C10—C13—C14	−3.0 (2)	C21—C22—C23—C18	−1.5 (2)
C11—C10—C13—C14	177.46 (15)	C19—C18—C23—C22	1.0 (2)
C9—C10—C13—O1	176.00 (12)	C17—C18—C23—C22	−178.89 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.95	2.56	3.3358 (18)	138
C5—H5A···Cg1ⁱⁱ	0.95	2.69	3.4762 (16)	141

Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈O₃
M_r	354.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	170
a, b, c (Å)	19.8766 (8), 6.9914 (3), 13.2603 (6)
β (°)	107.735 (4)
V (Å³)	1755.15 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.22 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.981, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	19756, 4534, 3310
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.143, 1.01
No. of reflections	4534
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3ⁱ	0.95	2.56	3.3358 (18)	138
C5—H5A···Cg1ⁱⁱ	0.95	2.69	3.4762 (16)	141

Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2.

π-π-stacking interactions. top

CgI···CgJ	CgI···CgJ (Å)	CgI···Perp (Å)	CgJ···Perp (Å)
Cg2···Cg3ⁱ	3.8752 (8)	3.5136 (6)	-3.4926 (6)
Cg2···Cg3ⁱⁱ	3.8331 (8)	-3.4772 (6)	3.4889 (6)

Cg2 and Cg3 are the centroids of rings O1/C13–C16 and C18–C23, respectively.

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

Acknowledgements

ASD thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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Volume 67| Part 9| September 2011| Pages o2294-o2295

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