(E)-3-(Furan-2-yl)-1-(4-meth­oxy­phen­yl)prop-2-en-1-one

Kapoor, K.; Gupta, V.K.; Kant, R.; Pandya, J.R.; Lade, S.B.; Joshi, H.S.

doi:10.1107/S160053681104373X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3185

https://doi.org/10.1107/S160053681104373X

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(E)-3-(Furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one

Kamini Kapoor,^a Vivek K. Gupta,^a Rajni Kant,^a ^* Jalpa R. Pandya,^b Sunil B. Lade ^b and Hitendra S. Joshi ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics and Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bChemistry Department, Saurashtra University, Rajkot 360 005, India
^*Correspondence e-mail: rkant.ju@gmail.com

(Received 12 September 2011; accepted 21 October 2011; online 5 November 2011)

In the title molecule, C₁₄H₁₂O₃, the prop-2-en-1-one unit forms dihedral angles of 12.96 (5) and 7.89 (7)° with the 4-methoxyphenyl group and the furan ring, respectively. The furan and benzene rings form a dihedral angle of 8.56 (5)°. In the crystal, C—H⋯π and π–π interactions are observed between the benzene and heterocyclic rings [centroid–centroid distance = 3.760 (1) Å].

Related literature

For biological properties of chalcone derivatives, see: Hsieh et al. (1998 ); Anto et al. (1994 ); Bhat et al. (2005 ); Xue et al. (2004 ). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000 ); Dimmock et al. (1998 ). For related structures, see: Fun et al. (2008 ); Guo et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₂O₃
M_r = 228.24
Monoclinic, P 2₁ /n
a = 7.1583 (3) Å
b = 19.1516 (8) Å
c = 8.4293 (3) Å
β = 94.357 (4)°
V = 1152.26 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.976, T_max = 1.000
13386 measured reflections
2027 independent reflections
1546 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.096
S = 1.03
2027 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg1ⁱ	0.93	2.76	3.592 (2)	149
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104373X/gk2411sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104373X/gk2411Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104373X/gk2411Isup3.cml

checkCIF report

Comment top

Chalcones and its derivatives have attracted particular interest during the last few decades due to use of such system as the core structure in many drug substances covering wide range of pharmacological application. Chalcone derivatives are reported to possess a broad spectrum of biological properties (Bhat et al., 2005; Xue et al., 2004; Hsieh et al.,1998; Anto et al., 1994; De Vincenzo et al.,2000; Dimmock et al., 1998). The bond lengths and angles observed in (I) show normal values and are comparable with related structures (Fun et al., 2008; Guo et al., 2008). In (I), the molecule exhibits an E configuration with respect to the C2=C3 double bond with the C1—C2—C3—C4 torsion angle being 179.95 (15)°. The least-square plane through the enone moiety (O15C1C2C3) makes dihedral angles of 12.96 (5)° and 7.89 (7)° with the benzene and furan rings, respectively. The dihedral angle between the 4-methoxy-phenyl group and furan ring is 8.56 (5)°, indicating that they are slightly twisted reletive to each other. While no classical hydrogen bonds are present, the C—H···π hydrogen bonds (Cg1 is the centroid of the furan ring and Cg2 is the centroid of the benzene ring are stabilizing the crystal structure. The crystal structure is further stabilized by π-π interactions between the benzene ring at (x, y, z)and furan ring at (1 + x, y, z) [centroid separation = 3.760 (1) Å, interplanar spacing = 3.510 Å and centroid shift = 1.35 Å].

Related literature top

For biological properties of chalcone derivatives, see: Hsieh et al. (1998); Anto et al. (1994); Bhat et al. (2005); Xue et al. (2004). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000); Dimmock et al. (1998). For related structures, see: Fun et al. (2008); Guo et al. (2008).

Experimental top

A mixture of the p-methoxyacetophenone (1.5 g, 0.01 mol), furfural (0.9 ml, 0.01 mol) and 40% NaOH (1 ml) was stirred in methanol (8 ml) for 24 h to afford the title compound (m.p. 341 K). Single crystals suitable for X-ray measurements were obtained by recrystallization from methanol at room temperature.

Structure description top

For biological properties of chalcone derivatives, see: Hsieh et al. (1998); Anto et al. (1994); Bhat et al. (2005); Xue et al. (2004). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000); Dimmock et al. (1998). For related structures, see: Fun et al. (2008); Guo et al. (2008).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. ORTEP view of the title molecule with displacement ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules viewed down the c axis.

(E)-3-(Furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₄H₁₂O₃	F(000) = 480
M_r = 228.24	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 341 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.1583 (3) Å	Cell parameters from 5366 reflections
b = 19.1516 (8) Å	θ = 3.6–29.0°
c = 8.4293 (3) Å	µ = 0.09 mm⁻¹
β = 94.357 (4)°	T = 293 K
V = 1152.26 (8) Å³	Block, yellow
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Oxford Diffraction Xcalibur S diffractometer	2027 independent reflections
Radiation source: fine-focus sealed tube	1546 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 16.1049 pixels mm^-1	θ_max = 25.0°, θ_min = 3.6°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −22→22
T_min = 0.976, T_max = 1.000	l = −10→10
13386 measured 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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0349P)² + 0.2369P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2027 reflections	Δρ_max = 0.13 e Å⁻³
156 parameters	Δρ_min = −0.13 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: 0.0089 (17)

Crystal data top

C₁₄H₁₂O₃	V = 1152.26 (8) Å³
M_r = 228.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1583 (3) Å	µ = 0.09 mm⁻¹
b = 19.1516 (8) Å	T = 293 K
c = 8.4293 (3) Å	0.3 × 0.2 × 0.2 mm
β = 94.357 (4)°

Data collection top

Oxford Diffraction Xcalibur S diffractometer	2027 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	1546 reflections with I > 2σ(I)
T_min = 0.976, T_max = 1.000	R_int = 0.028
13386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
2027 reflections	Δρ_min = −0.13 e Å⁻³
156 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
C1	0.5604 (2)	0.90359 (8)	−0.00421 (19)	0.0538 (4)
C2	0.3963 (2)	0.85830 (8)	0.01140 (19)	0.0553 (4)
H2	0.3954	0.8290	0.0993	0.066*
C3	0.2496 (2)	0.85775 (8)	−0.09527 (19)	0.0548 (4)
H3	0.2546	0.8877	−0.1818	0.066*
C4	0.0853 (2)	0.81579 (8)	−0.09015 (19)	0.0543 (4)
C6	−0.0871 (3)	0.73468 (11)	0.0068 (2)	0.0783 (6)
H6	−0.1271	0.6994	0.0720	0.094*
C7	−0.1863 (3)	0.75916 (11)	−0.1198 (2)	0.0774 (6)
H7	−0.3048	0.7446	−0.1591	0.093*
C8	−0.0767 (2)	0.81144 (10)	−0.1830 (2)	0.0701 (5)
H8	−0.1095	0.8383	−0.2727	0.084*
C9	0.7104 (2)	0.90560 (8)	0.12703 (18)	0.0481 (4)
C10	0.7260 (2)	0.85704 (8)	0.24994 (19)	0.0545 (4)
H10	0.6348	0.8227	0.2552	0.065*
C11	0.8739 (2)	0.85887 (8)	0.3638 (2)	0.0581 (4)
H11	0.8827	0.8254	0.4440	0.070*
C12	1.0100 (2)	0.91016 (8)	0.36004 (19)	0.0519 (4)
C13	0.9963 (2)	0.95944 (8)	0.2403 (2)	0.0582 (4)
H13	1.0863	0.9943	0.2365	0.070*
C14	0.8480 (2)	0.95650 (8)	0.1263 (2)	0.0571 (4)
H14	0.8399	0.9899	0.0460	0.068*
C17	1.3024 (2)	0.95549 (10)	0.4718 (2)	0.0740 (5)
H17A	1.3600	0.9490	0.3737	0.111*
H17B	1.3931	0.9471	0.5596	0.111*
H17C	1.2567	1.0025	0.4773	0.111*
O5	0.08105 (16)	0.76778 (6)	0.02948 (13)	0.0675 (4)
O15	0.57315 (17)	0.93872 (7)	−0.12483 (15)	0.0750 (4)
O16	1.14981 (16)	0.90766 (6)	0.47907 (14)	0.0687 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0570 (10)	0.0505 (9)	0.0550 (10)	0.0044 (8)	0.0116 (8)	0.0056 (8)
C2	0.0572 (10)	0.0542 (10)	0.0547 (10)	−0.0003 (8)	0.0049 (8)	0.0055 (8)
C3	0.0612 (10)	0.0509 (9)	0.0527 (9)	0.0065 (8)	0.0076 (8)	−0.0005 (8)
C4	0.0568 (10)	0.0557 (10)	0.0503 (9)	0.0069 (8)	0.0032 (7)	−0.0081 (8)
C6	0.0736 (13)	0.0847 (14)	0.0782 (13)	−0.0259 (11)	0.0153 (10)	−0.0189 (11)
C7	0.0565 (11)	0.0969 (15)	0.0789 (14)	−0.0069 (11)	0.0047 (10)	−0.0358 (12)
C8	0.0661 (12)	0.0820 (13)	0.0605 (11)	0.0119 (10)	−0.0062 (9)	−0.0151 (10)
C9	0.0499 (9)	0.0438 (8)	0.0519 (9)	0.0006 (7)	0.0129 (7)	0.0024 (7)
C10	0.0534 (9)	0.0495 (9)	0.0609 (10)	−0.0112 (7)	0.0077 (8)	0.0065 (8)
C11	0.0611 (10)	0.0533 (10)	0.0596 (10)	−0.0100 (8)	0.0024 (8)	0.0121 (8)
C12	0.0513 (9)	0.0496 (9)	0.0554 (10)	−0.0028 (7)	0.0089 (7)	−0.0027 (8)
C13	0.0574 (10)	0.0506 (10)	0.0675 (11)	−0.0128 (8)	0.0112 (8)	0.0023 (8)
C14	0.0622 (10)	0.0494 (9)	0.0609 (10)	−0.0050 (8)	0.0126 (8)	0.0119 (8)
C17	0.0587 (11)	0.0759 (12)	0.0871 (14)	−0.0184 (9)	0.0024 (9)	−0.0030 (11)
O5	0.0650 (8)	0.0726 (8)	0.0642 (8)	−0.0123 (6)	−0.0009 (6)	−0.0002 (6)
O15	0.0731 (8)	0.0854 (9)	0.0663 (8)	−0.0068 (7)	0.0035 (6)	0.0267 (7)
O16	0.0625 (7)	0.0702 (8)	0.0717 (8)	−0.0168 (6)	−0.0055 (6)	0.0065 (6)

Geometric parameters (Å, º) top

C1—O15	1.2284 (18)	C9—C14	1.386 (2)
C1—C2	1.474 (2)	C9—C10	1.390 (2)
C1—C9	1.483 (2)	C10—C11	1.374 (2)
C2—C3	1.330 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.385 (2)
C3—C4	1.428 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—O16	1.3633 (18)
C4—C8	1.351 (2)	C12—C13	1.380 (2)
C4—O5	1.3667 (19)	C13—C14	1.378 (2)
C6—C7	1.322 (3)	C13—H13	0.9300
C6—O5	1.361 (2)	C14—H14	0.9300
C6—H6	0.9300	C17—O16	1.4307 (19)
C7—C8	1.402 (3)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600

O15—C1—C2	120.42 (15)	C11—C10—C9	121.16 (14)
O15—C1—C9	120.53 (15)	C11—C10—H10	119.4
C2—C1—C9	119.05 (14)	C9—C10—H10	119.4
C3—C2—C1	122.54 (15)	C10—C11—C12	120.51 (15)
C3—C2—H2	118.7	C10—C11—H11	119.7
C1—C2—H2	118.7	C12—C11—H11	119.7
C2—C3—C4	126.45 (15)	O16—C12—C13	124.72 (14)
C2—C3—H3	116.8	O16—C12—C11	115.88 (14)
C4—C3—H3	116.8	C13—C12—C11	119.40 (15)
C8—C4—O5	108.66 (15)	C14—C13—C12	119.35 (15)
C8—C4—C3	133.60 (17)	C14—C13—H13	120.3
O5—C4—C3	117.73 (13)	C12—C13—H13	120.3
C7—C6—O5	111.29 (18)	C13—C14—C9	122.40 (15)
C7—C6—H6	124.4	C13—C14—H14	118.8
O5—C6—H6	124.4	C9—C14—H14	118.8
C6—C7—C8	106.16 (17)	O16—C17—H17A	109.5
C6—C7—H7	126.9	O16—C17—H17B	109.5
C8—C7—H7	126.9	H17A—C17—H17B	109.5
C4—C8—C7	107.71 (18)	O16—C17—H17C	109.5
C4—C8—H8	126.1	H17A—C17—H17C	109.5
C7—C8—H8	126.1	H17B—C17—H17C	109.5
C14—C9—C10	117.17 (15)	C6—O5—C4	106.19 (14)
C14—C9—C1	119.32 (14)	C12—O16—C17	117.81 (13)
C10—C9—C1	123.45 (14)

O15—C1—C2—C3	−5.9 (2)	C1—C9—C10—C11	176.21 (15)
C9—C1—C2—C3	174.64 (15)	C9—C10—C11—C12	1.1 (3)
C1—C2—C3—C4	179.95 (14)	C10—C11—C12—O16	179.49 (15)
C2—C3—C4—C8	176.35 (18)	C10—C11—C12—C13	−0.3 (2)
C2—C3—C4—O5	−4.8 (2)	O16—C12—C13—C14	179.98 (15)
O5—C6—C7—C8	−0.2 (2)	C11—C12—C13—C14	−0.3 (2)
O5—C4—C8—C7	0.07 (19)	C12—C13—C14—C9	0.1 (2)
C3—C4—C8—C7	179.02 (17)	C10—C9—C14—C13	0.7 (2)
C6—C7—C8—C4	0.1 (2)	C1—C9—C14—C13	−176.87 (15)
O15—C1—C9—C14	11.8 (2)	C7—C6—O5—C4	0.3 (2)
C2—C1—C9—C14	−168.82 (13)	C8—C4—O5—C6	−0.21 (18)
O15—C1—C9—C10	−165.65 (15)	C3—C4—O5—C6	−179.35 (14)
C2—C1—C9—C10	13.8 (2)	C13—C12—O16—C17	−6.0 (2)
C14—C9—C10—C11	−1.2 (2)	C11—C12—O16—C17	174.30 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.93	2.76	3.592 (2)	149
C17—H17C···Cg2ⁱⁱ	0.96	3.07	3.788 (2)	132

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂O₃
M_r	228.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.1583 (3), 19.1516 (8), 8.4293 (3)
β (°)	94.357 (4)
V (Å³)	1152.26 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur S
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.976, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13386, 2027, 1546
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.096, 1.03
No. of reflections	2027
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1ⁱ	0.93	2.761	3.592 (2)	149

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Acknowledgements

RK acknowledges the Department of Science and Technology for use of the single-crystal X-ray diffractometer, sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He is also thankful to UGC for funding under a research project [No. 3704154/2009 (J&K) (SR)].

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