(E)-3-(2,6-Dichloro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

Benmekhbi, L.; Belhouas, R.; Bouacida, S.; Mosbah, S.; Bencharif, L.

doi:10.1107/S1600536809020145

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1472-o1473

doi:10.1107/S1600536809020145

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(E)-3-(2,6-Dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Lotfi Benmekhbi,^a Ratiba Belhouas,^b ^* Sofiane Bouacida,^c Salima Mosbah ^d and Leila Bencharif ^d

^aDépartement de Chimie et de Chimie Pharmaceutique, Université de Msila, 28000 Algeria, ^bFaculté de Chimie, USTHB, BP32, El-Alia, Bab-Ezzouar, Alger, Algeria, ^cLaboratoire de Chimie Moléculaire, du Contrôle de l'Environnement et de Mesures Physico-Chimiques, Faculté des Sciences, Département de Chimie, Université Mentouri, 25000 Constantine, Algeria, and ^dLaboratoire de Chimie des Matériaux, Université de Mentouri, 25000 Constantine, Algeria
^*Correspondence e-mail: belhouas.ratiba@yahoo.fr

(Received 5 May 2009; accepted 26 May 2009; online 6 June 2009)

In the title compound, C₁₆H₁₂Cl₂O₂, the dichlorophenyl and methoxyphenyl groups are linked by a prop-2-en-1-one group. The C=C double bond is trans configured. The molecule is not planar, as can be seen from the dihedral angle of 6.21 (7)° between the planes of the two rings. The crystal structure can be described by two types of crossed layers which are parallel to (110) and (1 $[\overline{1}]$ 0).

Related literature

For background to the applications of chalcones, see: Liu et al. (2003 ); Li et al. (1995 ); Hsieh et al. (1998 ); Barford et al. (2002 ); Rojas et al. (2002 ); Nerya et al. (2006 ); Yang et al. (2000 ); Ducki et al. (1998 ); Goto et al. (1991 ); Indira et al. (2002 ); Lawrence et al. (2001 ); Nielsen et al. (2005 ); Sarker & Nahar (2004 ); Sarojini et al. (2006 ). For related structures, see: Yathirajan et al. (2007 ); Butcher et al. (2007 ); Fischer et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂Cl₂O₂
M_r = 307.16
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.4793 (2) Å
b = 12.9807 (5) Å
c = 16.7819 (8) Å
V = 1411.46 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 100 K
0.37 × 0.28 × 0.2 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 1998 ) T_min = 0.824, T_max = 0.913
6643 measured reflections
3211 independent reflections
2964 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.05
3211 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1331 Friedel pairs
Flack parameter: 0.01 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1ⁱ	0.95	2.84	3.727	157
C7—H7⋯Cg2ⁱ	0.95	2.85	3.360	115
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

Data collection: APEX2 (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); 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 ) and DIAMOND (Brandenburg & Berndt, 2001 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020145/bq2141sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020145/bq2141Isup2.hkl

checkCIF report

Comment top

For a structurally simple group of compounds, chalcones have displayed an impressive array for biological activities, among which anti-malarial (Liu et al., 2003), anti protozoal (Li et al., 1995), anti-inflammatory (Hsieh et al., 1998), immunomodulatory (Barford et al., 2002), nitric oxid inhibition (Rojas et al., 2002), tyronase inhibition (Nerya et al., 2006), cytotoxic (Yang et al., 2000) and anticancer (Ducki et al., 1998) activities have been cited in literature.

Chalcone may be useful for the chemotherapy of leishmanisis among others (Lawrence et al., 2001), they are also used as antibiotics (Nielsen et al., 2005). They were synthesized by a base catalyzed Claisen-Schmidt condensation of aromatic aldehydes and ketones. A natural medicine genus Angelica is known to contain large number of naturally occurring chalcones (Sarker et al., 2004). Chalcone derivatives are recognized for NLO properties and have good crystallization ability (Goto et al., 1991; Indira et al., 2002; Sarojini et al., 2006).

Structure of few related chalcones viz., (2E) -1- (2,4-dichlorophenyl) -3-(2-hydrox-3-metoxyphenyl)prop -2-en-1-one (Yathirajan et al., 2007), (2E) -1- (3-hydroxyphenyl) -3-(4-methylphenyl)prop-2-en-1-one (Butcher et al., 2007), (2E)-3-(biphenyl-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (Fischer et al., 2007).

The molecular structure of (I), and the atomic numbering used, is illustrated in Fig. 1. A diagram of the layered crystal packing in the unit cell of (I) is shown in Fig. 2. A substituted chalcone adopts an E configuration with respect to the C=C bond of the enone unit. The molecule is not planar, as can be seen from the dihedral angle of 6.21 (7)° between the two rings. The crystal structure can be described by two types of crossed layers, parallel to (110) and (1–10) respectively (Fig. 2).

The packing is stabilized by Van der Walls interactions and by C—H···π interactions resulting in the formation of three dimensional network (Table 1.).

Related literature top

For backround to the applications of chalcones, see: Liu et al. (2003); Li et al. (1995); Hsieh et al. (1998); Barford et al. (2002); Rojas et al. (2002); Nerya et al. (2006); Yang et al. (2000); Ducki et al. (1998); Goto et al. (1991); Indira et al. (2002); Lawrence et al. (2001); Nielsen et al. (2005); Sarker & Nahar (2004); Sarojini et al. (2006). For related structures, see: Yathirajan et al. (2007); Butcher et al. (2007); Fischer et al. (2007). Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

Experimental top

To a mixture of 2,6 dichlorobenzaldehyde (1.75 g, 0.01 mol) and 4-methoxyacetophenone (1.50 g, 0.01 mol) in ethanol 20 ml in the presence of a catalytic amount of sodium hydroxide solution (5 ml) was added slowly with stirring (6 h), the contents of the flask were poured into ice cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and purified by recrystallization in ethanol. Crystal suitable for x-ray analysis was grown by slow evaporation of an acetone solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR2002 (Burla et al., 2003); 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) and DIAMOND (Brandenburg & Berndt, 2001).

Figures top

	Fig. 1. (Farrugia, 1997) The structure of the title compound with the atomic labeling scheme. Displacements are drawn at the 50% probability level.
	Fig. 2. (Brandenburg & Berndt, 2001) A diagram of the layered crystal packing in (I), viewed down the c axis.

(E)-3-(2,6-Dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₂Cl₂O₂	F(000) = 632
M_r = 307.16	D_x = 1.445 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3041 reflections
a = 6.4793 (2) Å	θ = 2.4–27.4°
b = 12.9807 (5) Å	µ = 0.46 mm⁻¹
c = 16.7819 (8) Å	T = 100 K
V = 1411.46 (10) Å³	Prism, colourless
Z = 4	0.37 × 0.28 × 0.2 mm

Data collection top

Bruker APEXII diffractometer	2964 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
CCD rotation images, thin slices scans	θ_max = 27.4°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS, Bruker, 1998)	h = −6→8
T_min = 0.824, T_max = 0.913	k = −15→16
6643 measured reflections	l = −20→21
3211 independent reflections

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0409P)² + 0.5074P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
3211 reflections	Δρ_max = 0.51 e Å⁻³
182 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1331 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (6)

Crystal data top

C₁₆H₁₂Cl₂O₂	V = 1411.46 (10) Å³
M_r = 307.16	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.4793 (2) Å	µ = 0.46 mm⁻¹
b = 12.9807 (5) Å	T = 100 K
c = 16.7819 (8) Å	0.37 × 0.28 × 0.2 mm

Data collection top

Bruker APEXII diffractometer	3211 independent reflections
Absorption correction: multi-scan (SADABS, Bruker, 1998)	2964 reflections with I > 2σ(I)
T_min = 0.824, T_max = 0.913	R_int = 0.029
6643 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.51 e Å⁻³
S = 1.05	Δρ_min = −0.20 e Å⁻³
3211 reflections	Absolute structure: Flack (1983), 1331 Friedel pairs
182 parameters	Absolute structure parameter: 0.01 (6)
0 restraints

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
Cl1	0.49869 (7)	1.03293 (4)	0.58897 (3)	0.02481 (12)
Cl5	0.06450 (7)	0.84015 (4)	0.35072 (3)	0.02267 (12)
C1	0.2990 (3)	0.95544 (14)	0.55269 (13)	0.0174 (4)
C2	0.1599 (3)	0.91924 (15)	0.60937 (13)	0.0211 (4)
H2	0.1779	0.9363	0.664	0.025*
C3	−0.0051 (3)	0.85821 (14)	0.58604 (13)	0.0226 (4)
H3	−0.1001	0.8333	0.6246	0.027*
C4	−0.0312 (3)	0.83360 (14)	0.50613 (12)	0.0206 (4)
H4	−0.1422	0.7907	0.4898	0.025*
C5	0.1068 (3)	0.87235 (14)	0.45044 (12)	0.0167 (4)
C6	0.2774 (3)	0.93459 (13)	0.47063 (13)	0.0149 (4)
C7	0.4050 (3)	0.97926 (13)	0.40676 (12)	0.0150 (4)
H7	0.3354	0.9928	0.358	0.018*
C8	0.6062 (3)	1.00344 (13)	0.40815 (13)	0.0169 (4)
H8	0.6877	0.9871	0.4535	0.02*
C9	0.7012 (3)	1.05587 (14)	0.33855 (12)	0.0172 (4)
O10	0.61836 (19)	1.05435 (10)	0.27255 (9)	0.0215 (3)
C11	0.8991 (3)	1.11288 (13)	0.35089 (12)	0.0154 (4)
C12	0.9741 (3)	1.13891 (13)	0.42704 (11)	0.0164 (4)
H12	0.9017	1.1168	0.4732	0.02*
C13	1.1527 (3)	1.19652 (14)	0.43510 (12)	0.0172 (4)
H13	1.2022	1.2139	0.4867	0.021*
C14	1.0073 (3)	1.14718 (13)	0.28402 (11)	0.0170 (4)
H14	0.9569	1.131	0.2324	0.02*
C15	1.1874 (3)	1.20463 (14)	0.29156 (12)	0.0173 (4)
H15	1.26	1.227	0.2455	0.021*
C16	1.2603 (3)	1.22906 (14)	0.36746 (12)	0.0172 (4)
O17	1.4376 (2)	1.28344 (10)	0.38116 (8)	0.0224 (3)
C18	1.5488 (3)	1.32052 (14)	0.31247 (13)	0.0225 (4)
H18A	1.5785	1.2628	0.2766	0.034*
H18B	1.6786	1.3522	0.3297	0.034*
H18C	1.4648	1.3718	0.2844	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0219 (2)	0.0314 (2)	0.0211 (3)	−0.0074 (2)	−0.0005 (2)	−0.0049 (2)
Cl5	0.0219 (2)	0.0227 (2)	0.0234 (3)	−0.0029 (2)	−0.0021 (2)	−0.0059 (2)
C1	0.0151 (8)	0.0157 (9)	0.0215 (11)	0.0023 (8)	−0.0002 (8)	0.0001 (8)
C2	0.0214 (10)	0.0226 (10)	0.0193 (11)	0.0027 (9)	0.0009 (8)	0.0047 (8)
C3	0.0193 (9)	0.0232 (9)	0.0255 (11)	−0.0005 (9)	0.0070 (9)	0.0083 (8)
C4	0.0156 (9)	0.0156 (8)	0.0305 (12)	−0.0028 (8)	0.0000 (8)	0.0023 (8)
C5	0.0157 (9)	0.0123 (8)	0.0221 (11)	0.0024 (8)	−0.0027 (8)	0.0005 (7)
C6	0.0129 (8)	0.0116 (8)	0.0203 (10)	0.0030 (7)	0.0014 (7)	0.0009 (7)
C7	0.0188 (9)	0.0112 (8)	0.0150 (10)	0.0024 (7)	−0.0008 (8)	0.0005 (8)
C8	0.0163 (9)	0.0161 (9)	0.0182 (11)	0.0025 (7)	−0.0013 (8)	0.0034 (8)
C9	0.0160 (8)	0.0161 (9)	0.0195 (11)	0.0034 (7)	0.0020 (8)	−0.0002 (8)
O10	0.0188 (6)	0.0280 (7)	0.0176 (8)	−0.0035 (6)	−0.0014 (6)	0.0022 (6)
C11	0.0140 (8)	0.0150 (8)	0.0172 (10)	0.0021 (7)	0.0000 (8)	0.0005 (8)
C12	0.0180 (9)	0.0168 (9)	0.0146 (10)	0.0039 (8)	0.0026 (7)	0.0019 (7)
C13	0.0212 (9)	0.0170 (9)	0.0135 (10)	0.0022 (8)	−0.0034 (8)	−0.0031 (7)
C14	0.0169 (8)	0.0193 (9)	0.0149 (9)	0.0017 (9)	−0.0016 (8)	0.0009 (7)
C15	0.0170 (9)	0.0185 (9)	0.0163 (10)	0.0003 (8)	0.0022 (8)	0.0040 (8)
C16	0.0166 (9)	0.0121 (8)	0.0228 (12)	0.0005 (8)	−0.0013 (7)	0.0013 (8)
O17	0.0214 (7)	0.0264 (7)	0.0195 (8)	−0.0088 (6)	−0.0016 (6)	0.0005 (6)
C18	0.0202 (10)	0.0218 (9)	0.0256 (11)	−0.0072 (8)	0.0001 (8)	0.0037 (8)

Geometric parameters (Å, º) top

Cl1—C1	1.7484 (19)	C9—C11	1.494 (3)
Cl5—C5	1.747 (2)	C11—C14	1.396 (3)
C1—C2	1.392 (3)	C11—C12	1.409 (3)
C1—C6	1.410 (3)	C12—C13	1.384 (3)
C2—C3	1.387 (3)	C12—H12	0.95
C2—H2	0.95	C13—C16	1.397 (3)
C3—C4	1.389 (3)	C13—H13	0.95
C3—H3	0.95	C14—C15	1.391 (3)
C4—C5	1.388 (3)	C14—H14	0.95
C4—H4	0.95	C15—C16	1.395 (3)
C5—C6	1.410 (3)	C15—H15	0.95
C6—C7	1.473 (3)	C16—O17	1.368 (2)
C7—C8	1.342 (2)	O17—C18	1.442 (2)
C7—H7	0.95	C18—H18A	0.98
C8—C9	1.485 (3)	C18—H18B	0.98
C8—H8	0.95	C18—H18C	0.98
C9—O10	1.231 (2)

C2—C1—C6	122.56 (18)	C8—C9—C11	118.26 (17)
C2—C1—Cl1	115.81 (16)	C14—C11—C12	118.64 (16)
C6—C1—Cl1	121.59 (15)	C14—C11—C9	118.51 (18)
C3—C2—C1	119.9 (2)	C12—C11—C9	122.73 (17)
C3—C2—H2	120	C13—C12—C11	120.46 (17)
C1—C2—H2	120	C13—C12—H12	119.8
C2—C3—C4	119.84 (18)	C11—C12—H12	119.8
C2—C3—H3	120.1	C12—C13—C16	120.05 (18)
C4—C3—H3	120.1	C12—C13—H13	120
C5—C4—C3	119.26 (17)	C16—C13—H13	120
C5—C4—H4	120.4	C15—C14—C11	121.28 (18)
C3—C4—H4	120.4	C15—C14—H14	119.4
C4—C5—C6	123.41 (19)	C11—C14—H14	119.4
C4—C5—Cl5	117.23 (14)	C14—C15—C16	119.28 (18)
C6—C5—Cl5	119.36 (15)	C14—C15—H15	120.4
C1—C6—C5	114.98 (18)	C16—C15—H15	120.4
C1—C6—C7	125.42 (17)	O17—C16—C15	123.72 (18)
C5—C6—C7	119.37 (18)	O17—C16—C13	116.00 (18)
C8—C7—C6	128.68 (19)	C15—C16—C13	120.27 (17)
C8—C7—H7	115.7	C16—O17—C18	117.23 (15)
C6—C7—H7	115.7	O17—C18—H18A	109.5
C7—C8—C9	119.76 (19)	O17—C18—H18B	109.5
C7—C8—H8	120.1	H18A—C18—H18B	109.5
C9—C8—H8	120.1	O17—C18—H18C	109.5
O10—C9—C8	121.29 (17)	H18A—C18—H18C	109.5
O10—C9—C11	120.44 (17)	H18B—C18—H18C	109.5

C6—C1—C2—C3	1.5 (3)	C7—C8—C9—C11	159.67 (16)
Cl1—C1—C2—C3	179.21 (14)	O10—C9—C11—C14	−12.1 (3)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C11—C14	169.21 (16)
C2—C3—C4—C5	−1.3 (3)	O10—C9—C11—C12	163.91 (17)
C3—C4—C5—C6	1.4 (3)	C8—C9—C11—C12	−14.8 (2)
C3—C4—C5—Cl5	−179.22 (14)	C14—C11—C12—C13	−0.6 (2)
C2—C1—C6—C5	−1.4 (3)	C9—C11—C12—C13	−176.57 (16)
Cl1—C1—C6—C5	−178.94 (13)	C11—C12—C13—C16	−0.2 (3)
C2—C1—C6—C7	173.05 (17)	C12—C11—C14—C15	1.0 (2)
Cl1—C1—C6—C7	−4.5 (3)	C9—C11—C14—C15	177.10 (16)
C4—C5—C6—C1	−0.1 (2)	C11—C14—C15—C16	−0.5 (3)
Cl5—C5—C6—C1	−179.47 (13)	C14—C15—C16—O17	178.75 (16)
C4—C5—C6—C7	−174.87 (16)	C14—C15—C16—C13	−0.3 (3)
Cl5—C5—C6—C7	5.8 (2)	C12—C13—C16—O17	−178.48 (15)
C1—C6—C7—C8	35.1 (3)	C12—C13—C16—C15	0.6 (3)
C5—C6—C7—C8	−150.75 (19)	C15—C16—O17—C18	2.6 (2)
C6—C7—C8—C9	−175.13 (17)	C13—C16—O17—C18	−178.31 (16)
C7—C8—C9—O10	−19.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1ⁱ	0.95	2.84	3.727	157
C7—H7···Cg2ⁱ	0.95	2.85	3.360	115

Symmetry code: (i) x+1/2, −y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂Cl₂O₂
M_r	307.16
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.4793 (2), 12.9807 (5), 16.7819 (8)
V (Å³)	1411.46 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.37 × 0.28 × 0.2

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS, Bruker, 1998)
T_min, T_max	0.824, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	6643, 3211, 2964
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.05
No. of reflections	3211
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.20
Absolute structure	Flack (1983), 1331 Friedel pairs
Absolute structure parameter	0.01 (6)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and DIAMOND (Brandenburg & Berndt, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1ⁱ	0.95	2.836	3.727	157
C7—H7···Cg2ⁱ	0.95	2.849	3.360	115

Symmetry code: (i) x+1/2, −y−1/2, −z.

Acknowledgements

The authors are grateful to Dr Thierry Roisnel, Centre de Diffractométrie X (CDIFX) de Rennes, Université de Rennes 1, France, for the data-collection facilities.

References

Barford, L., Kemp, K., Hansen, M. & Kharazmi, A. (2002). Int. Immunopharm. 2, 545–550. Google Scholar
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Butcher, R. J., Jasinski, J. P., Narayana, B., Lakshmana, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3660. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ducki, S., Forrest, R., Hadfield, J. A., Kendall, A., Lawrence, N. J., McGown, A. T. & Rennison, D. (1998). Bioorg. Med. Chem. Lett. 8, 1051–1055. Web of Science CrossRef CAS PubMed 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
Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007). Acta Cryst. E63, o1349–o1350. Web of Science CSD CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goto, Y., Hayashi, A., Kimura, Y. & Nakayama, M. (1991). J. Cryst. Growth, 108, 688–698. CrossRef CAS Web of Science Google Scholar
Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res. 15, 39–46. Web of Science CrossRef CAS PubMed Google Scholar
Indira, J., Karat, P. P. & Sarojini, B. K. (2002). J. Cryst. Growth, 242, 209–214. Web of Science CrossRef CAS Google Scholar
Lawrence, N. J., Rennison, D., McGown, A. T., Ducki, S., Gul, L. A., Hadfield, J. A. & Khan, N. (2001). J. Comb. Chem. 3, 421–426. Web of Science CrossRef PubMed CAS Google Scholar
Li, R., Kenyon, G. L., Cohen, F. E., Chen, X., Gong, B., Dominguez, J. N., Davidson, E., Nuzum, E. O., Rosenthal, P. J. & McKerrow, J. H. J. (1995). Med. Chem. 38, 5031–5033. CrossRef CAS Web of Science Google Scholar
Liu, M., Wilairat, P., Cropft, S. L., Tan, A. L. C. & Go, M. L. (2003). Bioorg. Med. Chem. 11, 2729–2733. Web of Science CrossRef PubMed CAS Google Scholar
Nerya, O., Musa, R., Khatib, S., Tamir, S. & Jacob, O. (2006). Phytochemistry, 65, 1389–1393. Web of Science CrossRef Google Scholar
Nielsen, S. F., Larsen, M., Boesen, T., Schοnning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667–2677. Web of Science CrossRef PubMed CAS Google Scholar
Rojas, J., Paya, M., Dominguez, J. N. & Ferrandiz, M. L. (2002). Bioorg. Med. Chem. Lett. 12, 1951–1953. Web of Science CrossRef PubMed CAS Google Scholar
Sarker, S. D. & Nahar, L. (2004). Curr. Med. Chem. 11, 1479–1500. Web of Science CrossRef PubMed CAS Google Scholar
Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54–59. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, Y., Xia, P., Bastow, K. F., Nakanishi, Y. & Lee, K. H. (2000). Bioorg. Med. Chem. Lett. 10, 699–701. Web of Science PubMed Google Scholar
Yathirajan, H. S., Mayekar, A. N., Narayana, B., Sarojini & Bolte, M. (2007). Acta Cryst. E63, o428–o429. CrossRef IUCr Journals Google Scholar