2-(4-Bromo­phen­yl)-6-methyl-4H-1-benzopyran-4-one (4′-bromo-6-methyl­flavone)

Janeczko, T.; Białońska, A.; Kostrzewa-Susłow, E.

doi:10.1107/S1600536810010718

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o966-o967

doi:10.1107/S1600536810010718

Open

access

2-(4-Bromophenyl)-6-methyl-4H-1-benzopyran-4-one (4′-bromo-6-methylflavone)

Tomasz Janeczko,^a Agata Białońska ^b ^* and Edyta Kostrzewa-Susłow ^a

^aDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, 25 Norwida, 50-375 Wrocław, Poland, and ^bFaculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, Poland
^*Correspondence e-mail: bialonsk@eto.wchuwr.pl

(Received 18 March 2010; accepted 22 March 2010; online 27 March 2010)

Planar (r.m.s. deviation from the plane through all non-H atoms = 0.036 Å) molecules of the title compound, C₁₆H₁₁BrO₂, form a layered structure stabilized by C—H⋯O hydrogen bonds and π–π stacking interactions.

Related literature

For background information on flavones and their properties, see: Hsiao et al. (2007 ); Manthey et al. (2001 ); Middleton et al. (2000 ). Millot et al. (2009 ); Moulari et al. (2006 ); Ren et al. (2003 ); Moon et al. (2007 ). For related structures, see: Kumar et al. (1998 ); Artali et al. (2003 ); Białońska et al. (2007 ); Ghalib et al. (2010 ).

Experimental

Crystal data

C₁₆H₁₁BrO₂
M_r = 315.16
Monoclinic, P 2₁ /c
a = 13.759 (3) Å
b = 6.873 (2) Å
c = 13.460 (2) Å
β = 90.25 (3)°
V = 1272.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.22 mm⁻¹
T = 100 K
0.31 × 0.29 × 0.04 mm

Data collection

Kuma KM-4-CCD diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Yarnton, England.]$ ); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 )] T_min = 0.474, T_max = 0.893
25822 measured reflections
5962 independent reflections
3659 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.070
S = 0.88
5962 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4ⁱ	0.95	2.49	3.2904 (17)	142
C16—H16A⋯O4ⁱ	0.95	2.58	3.4394 (16)	151
Symmetry code: (i) -x+1, -y, -z+1.

Table 2
π–π interactions (Å, °)

Cg(1) and Cg(2) are the centroids of the C5–C10 and C11–C16 rings, respectively.

Cg(I)	Cg(J)	Cg–Cg	Alpha	CgI_perp	CgJ_Perp	Slippage
Cg(1)	Cg(2)ⁱ	3.895	7.13 (3)	3.579 (2)	−3.430 (2)	1.84
Cg(1)	Cg(2)ⁱⁱ	3.843	7.13 (3)	−3.266 (2)	3.438 (2)	1.72
Notes: Cg–Cg = distance between ring centroids; Alpha = dihedral angle between planes I and J; CgI_Perp = perpendicular distance of Cg(I) on ring J; CgJ_Perp = perpendicular distance of Cg(J) on ring I; Slippage = distance between Cg(I) and perpendicular projection of Cg(J) on Ring I. Symmetry codes: (i) $[1-x, -{1\over2}+y, {1\over2} - z]$ ; (ii) $[1-x, {1\over2}+y, {1\over2}-z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010718/ds2025sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010718/ds2025Isup2.hkl

checkCIF report

Comment top

Seeds, fruit skin, bark and flowers of most plants contain significant amount of flavonoids. They have been classified to one subclass of flavonoids according to their chemical structures (Hsiao et al., 2007). Several naturally occurring and synthetic flavones are well know in respect to their anti-oxidant, anti-neoplastic, anti-malarial, anti-inflammatory and insecticidal activity (Manthey et al., 2001; Millot et al., 2009; Moulari et al., 2006). Halogenoflavones have been used as precursors for the synthesis of a variety of bioactive organic compounds including biflavodoids (Ren et al., 2003; Moon et al., 2007). The title compound is a flavone derivative with 4'-bromo and 6-methyl substituents in the biologically active region (Scheme) (Middleton et al., 2000).

Crystal structures of the following related flavones were reported: 7-hydroxyflavone monohydrate (Kumar et al., 1998), 6-(3-hydroxy-3-methylbut-1-ynyl)-flavone and 6-(3-methylbut-3-en-1-ynyl)-flavone (Artali et al., 2003), 2-phenyl-6-hydroxy-4H-1-benzopyran-4-one (6-hydroxyflavone) (Białońska et al., 2007), 3,5,4'-trihydroxy-6,7-dimethoxy-flavone (Eupalitin) (Ghalib et al., 2010).

Structure of 2-(4-bromophenyl)-6-methyl-4H-1-benzopyran-4-one with the numbering scheme employed is presented in Fig. 1 Molecules of the titled compound form ribbons stabilized by π–π stacking interactions exteded along the [010] direction (Table 2). The neighboring ribbons are linked by C—H···O hydrogen bonds, in which the carbonyl O4 atom is their acceptor (Table 1). The resulting layers perpendicular to the [100] direction (Fig. 2).

Related literature top

For background information on flavones and their properties, see: Hsiao et al. (2007); Manthey et al. (2001); Middleton et al. (2000). Millot et al. (2009); Moulari et al. (2006); Ren et al. (2003); Moon et al. (2007). For related structures, see: Kumar et al. (1998); Artali et al. (2003); Białońska et al. (2007); Ghalib et al. (2010).

Experimental top

The title compound was obtained according to the procedure: A mixture of the para-cresol 1,08 g (10,0 mmol) and 3,4'-dibromopropiophenone 0,59 g (2,0 mmol) in BF3.OEt2 (20 ml) was heated at 60 °C and stirred for 8 h. The products of reaction were extracted from the mixtures with chloroform. Titled product was separated by column chromatography on silica gel with hexane/methyl chloride/acetone (10:1:1 v/v/v) as eluent (Scheme). Crystals suitable for X-ray structure analysis were obtained by slow evaporation from the eluent at room temperature. Structure of the titled product was confirmed by means of the 1H NMR and 13 C NMR spectra. 1H NMR (600 MHz, CDCl3 δ, p.p.m.): 6.81 (s, 1H, H3), 7.48 (d, 1H, J=8.56 Hz, H8), 7.54 (dd, 1H, J=8.56, 2.12 Hz, H7), 7.68 (m, 2H Wh=8.60 Hz, H5' and H7'), 7.80 (m, 2H, Wh=8.60 Hz, H2' and H6'), 8.04 (d, 1H, J=2.12 Hz, H-5). 13 C NMR (150 MHz, CDCl3 δ, p.p.m.): 20.98 (-CH3); 107.55 (C3); 117.83 (C8); 123.56 (C10); 125.13 (C5); 126.25 (C6); 127.71 (C3' i C5'); 130.84 (C1'); 132.35 (C2' i C6'); 135.21 (C7); 135.47 (C4'); 154.48 (C9) 162.23 (C2); 178.48 (C4).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Selected view of 4'-bromo-6-methyloflavone with the numbering scheme employed.
	Fig. 2. Molecular packing of 4'-bromo-6-methyloflavone.

2-(4-Bromophenyl)-6-methyl-4H-1-benzopyran-4-one top

Crystal data top

C₁₆H₁₁BrO₂	F(000) = 632
M_r = 315.16	D_x = 1.645 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11464 reflections
a = 13.759 (3) Å	θ = 3.0–36.9°
b = 6.873 (2) Å	µ = 3.22 mm⁻¹
c = 13.460 (2) Å	T = 100 K
β = 90.25 (3)°	Plate, colorless
V = 1272.8 (5) Å³	0.31 × 0.29 × 0.04 mm
Z = 4

Data collection top

Kuma KM-4-CCD diffractometer	5962 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scan	θ_max = 36.0°, θ_min = 3.0°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	h = −22→22
T_min = 0.474, T_max = 0.893	k = −11→10
25822 measured reflections	l = −21→22

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.0385P)²] where P = (F_o² + 2F_c²)/3
5962 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₆H₁₁BrO₂	V = 1272.8 (5) Å³
M_r = 315.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.759 (3) Å	µ = 3.22 mm⁻¹
b = 6.873 (2) Å	T = 100 K
c = 13.460 (2) Å	0.31 × 0.29 × 0.04 mm
β = 90.25 (3)°

Data collection top

Kuma KM-4-CCD diffractometer	5962 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	3659 reflections with I > 2σ(I)
T_min = 0.474, T_max = 0.893	R_int = 0.047
25822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 0.88	Δρ_max = 0.69 e Å⁻³
5962 reflections	Δρ_min = −0.37 e Å⁻³
172 parameters

Special details top

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br	0.122301 (8)	0.12666 (2)	0.048602 (10)	0.02299 (4)
O1	0.59232 (6)	0.12638 (15)	0.20324 (6)	0.01526 (15)
C2	0.51619 (8)	0.12091 (19)	0.26748 (8)	0.01346 (19)
C3	0.52887 (8)	0.1170 (2)	0.36736 (8)	0.0158 (2)
H3A	0.4733	0.1138	0.4089	0.019*
O4	0.63780 (7)	0.11445 (16)	0.50391 (6)	0.02132 (18)
C4	0.62442 (8)	0.1176 (2)	0.41278 (9)	0.0152 (2)
C5	0.80289 (8)	0.1197 (2)	0.37337 (9)	0.0158 (2)
H5A	0.8173	0.1160	0.4424	0.019*
C6	0.87838 (8)	0.1235 (2)	0.30587 (9)	0.0173 (2)
C7	0.85504 (9)	0.1311 (2)	0.20364 (9)	0.0188 (2)
H7A	0.9062	0.1348	0.1565	0.023*
C8	0.76018 (9)	0.1335 (2)	0.17014 (9)	0.0179 (2)
H8A	0.7459	0.1396	0.1011	0.021*
C9	0.70523 (8)	0.1212 (2)	0.34182 (8)	0.01366 (19)
C10	0.68548 (8)	0.1267 (2)	0.24016 (9)	0.01469 (19)
C11	0.42181 (8)	0.12034 (19)	0.21497 (8)	0.01378 (19)
C12	0.41819 (9)	0.1370 (2)	0.11092 (9)	0.0170 (2)
H12A	0.4768	0.1477	0.0743	0.020*
C13	0.32929 (9)	0.1380 (2)	0.06124 (9)	0.0181 (2)
H13A	0.3269	0.1486	−0.0091	0.022*
C14	0.24418 (8)	0.1234 (2)	0.11563 (9)	0.0169 (2)
C15	0.24576 (9)	0.1070 (2)	0.21903 (10)	0.0184 (2)
H15A	0.1869	0.0980	0.2553	0.022*
C16	0.33448 (9)	0.1041 (2)	0.26785 (9)	0.0166 (2)
H16A	0.3363	0.0910	0.3381	0.020*
C17	0.98418 (9)	0.1213 (2)	0.33957 (10)	0.0217 (2)
H17A	0.9871	0.1160	0.4123	0.033*
H17B	1.0167	0.2396	0.3163	0.033*
H17C	1.0168	0.0069	0.3118	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.01513 (6)	0.02745 (7)	0.02633 (7)	0.00270 (6)	−0.00771 (4)	−0.00266 (6)
O1	0.0108 (3)	0.0227 (4)	0.0123 (3)	−0.0008 (4)	−0.0008 (3)	0.0003 (4)
C2	0.0130 (4)	0.0128 (5)	0.0145 (5)	−0.0002 (5)	0.0009 (4)	0.0007 (5)
C3	0.0135 (4)	0.0200 (5)	0.0139 (5)	−0.0007 (5)	0.0013 (4)	0.0001 (5)
O4	0.0200 (4)	0.0308 (5)	0.0132 (4)	−0.0045 (4)	−0.0010 (3)	0.0008 (4)
C4	0.0155 (5)	0.0155 (5)	0.0145 (5)	−0.0015 (5)	−0.0006 (4)	0.0003 (5)
C5	0.0146 (5)	0.0159 (5)	0.0169 (5)	−0.0008 (5)	−0.0031 (4)	−0.0006 (5)
C6	0.0128 (4)	0.0177 (5)	0.0215 (5)	−0.0009 (5)	−0.0020 (4)	−0.0009 (5)
C7	0.0137 (5)	0.0232 (6)	0.0195 (5)	−0.0004 (5)	0.0019 (4)	−0.0014 (6)
C8	0.0147 (5)	0.0239 (6)	0.0150 (5)	−0.0004 (5)	0.0004 (4)	−0.0012 (5)
C9	0.0124 (4)	0.0143 (5)	0.0144 (5)	−0.0010 (5)	−0.0005 (4)	0.0002 (5)
C10	0.0115 (4)	0.0157 (5)	0.0168 (5)	−0.0008 (5)	−0.0012 (4)	−0.0007 (5)
C11	0.0122 (4)	0.0138 (5)	0.0154 (5)	−0.0001 (5)	−0.0015 (4)	−0.0002 (5)
C12	0.0149 (5)	0.0191 (6)	0.0171 (5)	−0.0007 (5)	−0.0005 (4)	0.0017 (5)
C13	0.0178 (5)	0.0195 (6)	0.0170 (5)	−0.0008 (5)	−0.0031 (4)	0.0008 (5)
C14	0.0144 (5)	0.0160 (5)	0.0203 (5)	0.0017 (5)	−0.0046 (4)	−0.0008 (5)
C15	0.0139 (5)	0.0196 (6)	0.0216 (6)	0.0003 (5)	−0.0001 (4)	−0.0012 (5)
C16	0.0138 (5)	0.0198 (6)	0.0163 (5)	−0.0001 (5)	0.0000 (4)	−0.0002 (5)
C17	0.0140 (5)	0.0270 (6)	0.0240 (6)	0.0002 (6)	−0.0036 (4)	−0.0022 (6)

Geometric parameters (Å, º) top

Br—C14	1.9008 (13)	C8—C10	1.3983 (16)
O1—C2	1.3617 (14)	C8—H8A	0.9500
O1—C10	1.3727 (14)	C9—C10	1.3944 (16)
C2—C3	1.3551 (16)	C11—C16	1.4036 (17)
C2—C11	1.4757 (16)	C11—C12	1.4059 (16)
C3—C4	1.4475 (17)	C12—C13	1.3914 (17)
C3—H3A	0.9500	C12—H12A	0.9500
O4—C4	1.2397 (15)	C13—C14	1.3875 (17)
C4—C9	1.4692 (16)	C13—H13A	0.9500
C5—C6	1.3832 (17)	C14—C15	1.3964 (18)
C5—C9	1.4075 (16)	C15—C16	1.3839 (17)
C5—H5A	0.9500	C15—H15A	0.9500
C6—C7	1.4126 (18)	C16—H16A	0.9500
C6—C17	1.5228 (17)	C17—H17A	0.9800
C7—C8	1.3792 (17)	C17—H17B	0.9800
C7—H7A	0.9500	C17—H17C	0.9800

C2—O1—C10	119.33 (9)	O1—C10—C8	116.36 (10)
C3—C2—O1	122.30 (10)	C9—C10—C8	121.44 (10)
C3—C2—C11	125.75 (11)	C16—C11—C12	119.01 (11)
O1—C2—C11	111.95 (9)	C16—C11—C2	120.72 (10)
C2—C3—C4	122.12 (11)	C12—C11—C2	120.27 (10)
C2—C3—H3A	118.9	C13—C12—C11	120.42 (11)
C4—C3—H3A	118.9	C13—C12—H12A	119.8
O4—C4—C3	123.27 (11)	C11—C12—H12A	119.8
O4—C4—C9	122.28 (11)	C14—C13—C12	119.23 (11)
C3—C4—C9	114.45 (10)	C14—C13—H13A	120.4
C6—C5—C9	121.35 (11)	C12—C13—H13A	120.4
C6—C5—H5A	119.3	C13—C14—C15	121.48 (11)
C9—C5—H5A	119.3	C13—C14—Br	119.58 (9)
C5—C6—C7	118.19 (11)	C15—C14—Br	118.94 (9)
C5—C6—C17	121.59 (11)	C16—C15—C14	118.97 (12)
C7—C6—C17	120.23 (11)	C16—C15—H15A	120.5
C8—C7—C6	121.99 (11)	C14—C15—H15A	120.5
C8—C7—H7A	119.0	C15—C16—C11	120.88 (12)
C6—C7—H7A	119.0	C15—C16—H16A	119.6
C7—C8—C10	118.46 (11)	C11—C16—H16A	119.6
C7—C8—H8A	120.8	C6—C17—H17A	109.5
C10—C8—H8A	120.8	C6—C17—H17B	109.5
C10—C9—C5	118.56 (10)	H17A—C17—H17B	109.5
C10—C9—C4	119.58 (10)	C6—C17—H17C	109.5
C5—C9—C4	121.87 (10)	H17A—C17—H17C	109.5
O1—C10—C9	122.20 (10)	H17B—C17—H17C	109.5

C10—O1—C2—C3	0.45 (19)	C4—C9—C10—O1	−0.9 (2)
C10—O1—C2—C11	−179.69 (13)	C5—C9—C10—C8	−0.9 (2)
O1—C2—C3—C4	−0.3 (2)	C4—C9—C10—C8	178.91 (13)
C11—C2—C3—C4	179.90 (13)	C7—C8—C10—O1	−179.04 (14)
C2—C3—C4—O4	179.89 (13)	C7—C8—C10—C9	1.2 (2)
C2—C3—C4—C9	−0.5 (2)	C3—C2—C11—C16	−3.7 (2)
C9—C5—C6—C7	0.7 (2)	O1—C2—C11—C16	176.44 (12)
C9—C5—C6—C17	−179.82 (14)	C3—C2—C11—C12	175.99 (13)
C5—C6—C7—C8	−0.4 (2)	O1—C2—C11—C12	−3.86 (18)
C17—C6—C7—C8	−179.95 (14)	C16—C11—C12—C13	0.2 (2)
C6—C7—C8—C10	−0.5 (2)	C2—C11—C12—C13	−179.51 (13)
C6—C5—C9—C10	0.0 (2)	C11—C12—C13—C14	0.3 (2)
C6—C5—C9—C4	−179.84 (13)	C12—C13—C14—C15	−0.2 (2)
O4—C4—C9—C10	−179.34 (13)	C12—C13—C14—Br	179.51 (11)
C3—C4—C9—C10	1.0 (2)	C13—C14—C15—C16	−0.4 (2)
O4—C4—C9—C5	0.5 (2)	Br—C14—C15—C16	179.84 (11)
C3—C4—C9—C5	−179.17 (13)	C14—C15—C16—C11	1.0 (2)
C2—O1—C10—C9	0.1 (2)	C12—C11—C16—C15	−0.8 (2)
C2—O1—C10—C8	−179.67 (12)	C2—C11—C16—C15	178.85 (14)
C5—C9—C10—O1	179.28 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4ⁱ	0.95	2.49	3.2904 (17)	142
C16—H16A···O4ⁱ	0.95	2.58	3.4394 (16)	151

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁BrO₂
M_r	315.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.759 (3), 6.873 (2), 13.460 (2)
β (°)	90.25 (3)
V (Å³)	1272.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.22
Crystal size (mm)	0.31 × 0.29 × 0.04

Data collection
Diffractometer	Kuma KM-4-CCD diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.474, 0.893
No. of measured, independent and observed [I > 2σ(I)] reflections	25822, 5962, 3659
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.827

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.070, 0.88
No. of reflections	5962
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.37

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4ⁱ	0.95	2.49	3.2904 (17)	142.2
C16—H16A···O4ⁱ	0.95	2.58	3.4394 (16)	151.2

Symmetry code: (i) −x+1, −y, −z+1.

π–π interactions (Å, °). top

Cg(1) and Cg(2) are the centroids of the C5–C10 and C11–C16 rings, respectively.

Cg(I)	Cg(J)	Cg–Cg	Alpha	CgI_perp	CgJ_Perp	Slippage
Cg(1)	Cg(2)ⁱ	3.895	7.13 (3)	3.579 (2)	-3.430 (2)	1.84
Cg(1)	Cg(2)ⁱⁱ	3.843	7.13 (3)	-3.266 (2)	3.438 (2)	1.72

Notes: Cg–Cg = distance between ring centroids; Alpha = dihedral angle between planes I and J; CgI_Perp = perpendicular distance of Cg(I) on ring J; CgJ_Perp = perpendicular distance of Cg(J) on ring I; Slippage = distance between Cg(I) and perpendicular projection of Cg(J) on Ring I. Symmetry codes: (i) 1-x, -0.5+y, 0.5-z, (ii) 1-x, 0.5+y, 0.5-z.

References

Artali, R., Barili, P. L., Bombieri, G., Re, P. D., Marchini, N., Meneghetti, F. & Valenti, P. (2003). Farmaco, 58, 875–881. CSD CrossRef PubMed CAS Google Scholar
Białońska, A., Ciunik, Z., Kostrzewa-Susłow, E. & Dmochowska-Gładysz, J. (2007). Acta Cryst. E63, o430–o431. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1999). XP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ghalib, R. M., Mehdi, S. H., Hashim, R., Sulaiman, O., Valkonen, A., Rissanen, K. & Trifunović, S. R. (2010). J. Chem. Crystallogr. doi, 10,1007/s10870-010-9687-9. Google Scholar
Hsiao, Y.-C., Kuo, W.-H., Chen, P.-N., Chang, H.-R., Lin, T.-H., Yang, W.-E., Hsieh, Y.-S. & Chu, S.-C. (2007). Chem. Biol. Interact. 167, 193–206. Web of Science CrossRef PubMed CAS Google Scholar
Kumar, S., Ramanathan, T., Subramanian, K. & Steiner, T. (1998). J. Chem. Crystallogr. 28, 931–933. Web of Science CSD CrossRef CAS Google Scholar
Manthey, J. A., Grohmann, K. & Guthrie, N. (2001). Curr. Med. Chem. 8, 135–153. Web of Science CrossRef PubMed CAS Google Scholar
Middleton, E. Jr, Kandaswami, C. & Theoharides, T. C. (2000). Pharmacol. Rev. 52, 673–751. Web of Science PubMed CAS Google Scholar
Millot, M., Tomasi, S., Studzinska, S., Rouaud, I. & Boustie, J. (2009). J. Nat. Prod. 72, 2177–2180. Web of Science CrossRef PubMed CAS Google Scholar
Moon, T. C., Quan, Z., Kim, J., Kim, H. P., Kudo, I., Murakami, M., Park, H. & Chang, H. W. (2007). Bioorg. Med. Chem. 15, 7138–7143. Web of Science CrossRef PubMed CAS Google Scholar
Moulari, B., Pellequer, Y., Lboutounne, H., Girard, C., Chaumont, J. P., Millet, J. & Muyard, F. (2006). J. Ethnopharmacol. 106, 272–278. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Yarnton, England. Google Scholar
Ren, W., Qiao, Z., Wang, H., Zhu, L. & Zhang, L. (2003). Med. Res. Rev. 23, 519–534. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o966-o967

doi:10.1107/S1600536810010718

Open

access