2-{[(E)-2-Hy­droxy­benzyl­idene]amino}-1H-isoindole-1,3(2H)-dione

Devarajegowda, H.C.; Revanasiddappa, H.D.; Kumar, L.S.; Sumangala, V.; Prasad, V.D.J.

doi:10.1107/S1600536810038407

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2703

https://doi.org/10.1107/S1600536810038407

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2-{[(E)-2-Hydroxybenzylidene]amino}-1H-isoindole-1,3(2H)-dione

H. C. Devarajegowda,^a ^* H. D. Revanasiddappa,^b L. Shiva Kumar,^b V. Sumangala ^c and V. D. Jagadeesh Prasad ^d

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, Karnataka, India, ^cSequent Scientific India Limited, Baikampadi, Mangalore, Karnataka, India, and ^dDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 18 September 2010; accepted 25 September 2010; online 2 October 2010)

In the title compound, C₁₅H₁₀N₂O₃, the isoindoline ring system is almost planar [maximum deviation = 0.020 (2) Å] and makes a dihedral angle of 1.57 (7)° with the benzene ring. Intramolecular O—H⋯N and C—H⋯O hydrogen bonds are observed.

Related literature

Based on the multiple binding sites of acetylcholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives have been designed and synthesized, see: Zhao et al. (2009 ). Phthalimide derivatives have also been developed as LXRa-selective antagonists, see: Motoshima et al. (2009 ). For the biological activity of Schiff bases, see: Singh et al. (2006 ); Sithambaram et al. (2006 ); Walsh et al. (1996 ). For a related structure, see: Jing et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₀N₂O₃
M_r = 266.25
Monoclinic, P 2₁ /c
a = 7.0877 (2) Å
b = 8.2400 (4) Å
c = 21.2752 (7) Å
β = 92.659 (3)°
V = 1241.19 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.982, T_max = 0.988
11806 measured reflections
2184 independent reflections
1541 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.10
2184 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2	0.82	1.90	2.6152 (16)	145
C9—H9⋯O4	0.93	2.24	2.8937 (19)	127

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810038407/wn2411sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038407/wn2411Isup2.hkl

checkCIF report

Comment top

Based on the multiple binding sites of acetylcholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives were designed and synthesized (Zhao et al., 2009). Phthalimide derivatives have also been developed as LXRa-selective antagonists (Motoshima et al., 2009). Azomethine group-containing compounds, typically known as Schiff bases, form a significant class of compounds in medicinal and pharmaceutical chemistry, with several biological applications that include antibacterial (Sithambaram Karthikeyan et al., 2006), antifungal (Singh et al., 2006) and antitumor activity (Walsh et al., 1996).

The asymmetric unit of 2-{[(1E)-(2-hydroxyphenyl)methylene]amino} -1H-isoindole-1,3(2H)-dione contains one molecule (Fig. 1). The isoindoline ring system is almost planar [maximum deviation = 0.020 (2) Å] and makes a dihedral angle of 1.57 (7)° with the benzene ring. The bond distances and bond angles are in good agreement with those in a closely related crystal structure (Jing et al., 2007).

In the crystal structure, molecules intramolecula O5—H5···N2 and C9—H9···O4 hydrogen bonds are observed (Table 1). The packing of the molecules shows stacking when viewed along the b axis (Fig. 2).

Related literature top

Based on the multiple binding sites of acetylcholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives have been designed and synthesized, see: Zhao et al. (2009). Phthalimide derivatives have also been developed as LXRa-selective antagonists, see: Motoshima et al. (2009). For the biological activity of Schiff bases, see: Singh et al. (2006); Sithambaram Karthikeyan et al. (2006); Walsh et al. (1996). For a related structure, see: Jing et al. (2007).

Experimental top

Salicylaldehyde (1.221 g, 10 mmol) was dissolved in 20 ml ethanol and added, with continuous stirring, to a hot ethanolic solution (30 ml) containing N-aminophthalimide (1.621 g, 10 mmol). The mixture was further stirred, refluxed for 5 h and allowed to stand overnight. The final yellow product was dissolved in ethanol and a single crystal of the title compound was obtained after slow evaporation of the solvent at room temperature (Yield: 89%; M.p. 465 K).

Structure description top

Based on the multiple binding sites of acetylcholinesterase (AChE), a series of AChE inhibitors involving phthalimide derivatives have been designed and synthesized, see: Zhao et al. (2009). Phthalimide derivatives have also been developed as LXRa-selective antagonists, see: Motoshima et al. (2009). For the biological activity of Schiff bases, see: Singh et al. (2006); Sithambaram Karthikeyan et al. (2006); Walsh et al. (1996). For a related structure, see: Jing et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with the displacement ellipsoids drawn at the 50% probability level. The H atoms are shown as spheres of arbitrary radius. Dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. A view of the crystal structure down the b axis. Dashed lines indicate intramolecular hydrogen bonds.

2-{[(E)-2-Hydroxybenzylidene]amino}-1H-isoindole- 1,3(2H)-dione top

Crystal data top

C₁₅H₁₀N₂O₃	F(000) = 552
M_r = 266.25	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 465 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0877 (2) Å	Cell parameters from 2184 reflections
b = 8.2400 (4) Å	θ = 2.7–25.0°
c = 21.2752 (7) Å	µ = 0.10 mm⁻¹
β = 92.659 (3)°	T = 293 K
V = 1241.19 (8) Å³	Plate, yellow
Z = 4	0.22 × 0.15 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2184 independent reflections
Radiation source: fine-focus sealed tube	1541 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and φ scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
T_min = 0.982, T_max = 0.988	k = −9→9
11806 measured reflections	l = −25→25

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0449P)² + 0.0801P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2184 reflections	Δρ_max = 0.10 e Å⁻³
182 parameters	Δρ_min = −0.11 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: 0.0088 (16)

Crystal data top

C₁₅H₁₀N₂O₃	V = 1241.19 (8) Å³
M_r = 266.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0877 (2) Å	µ = 0.10 mm⁻¹
b = 8.2400 (4) Å	T = 293 K
c = 21.2752 (7) Å	0.22 × 0.15 × 0.12 mm
β = 92.659 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2184 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1541 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.023
11806 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.10	Δρ_max = 0.10 e Å⁻³
2184 reflections	Δρ_min = −0.11 e Å⁻³
182 parameters

Special details top

Experimental. IR ν(Nujolmull, cm^-1): 1768 and 1725 (C=O), 1617 (HC=N), 3386 (Ph—OH). ¹H NMR (DMSO-d₆, p.p.m.): 10.67 (s, 1H, Ph—OH), 9.45 (s, 1H, HC=N), 6.92–7.91 (m, 4H, Ar—H). FAB-MS: m/z = 267 [M+1]⁺, Anal. Calc. for C₁₅H₁₀N₂O₃; C, 67.67; H, 3.79; N, 10.52; O, 18.03; Found: C, 67.05; H, 3.81; N, 10.68; O, 17.98,; Electronic spectra: 289 nm and 334 nm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O3	−0.27271 (15)	0.27296 (16)	0.07498 (5)	0.0836 (4)
O4	0.28488 (17)	0.31121 (18)	−0.02433 (5)	0.0877 (4)
O5	0.00226 (15)	0.52524 (17)	0.19986 (5)	0.0846 (4)
H5	−0.0194	0.4752	0.1670	0.127*
N1	0.02621 (17)	0.31346 (16)	0.03847 (5)	0.0579 (4)
N2	0.08319 (18)	0.40089 (16)	0.09127 (5)	0.0591 (4)
C1	−0.3130 (3)	0.0248 (2)	−0.11364 (9)	0.0780 (5)
H1	−0.4146	−0.0282	−0.1338	0.094*
C2	−0.1434 (3)	0.0318 (2)	−0.14198 (8)	0.0798 (5)
H2	−0.1320	−0.0162	−0.1812	0.096*
C3	0.0112 (3)	0.1090 (2)	−0.11336 (8)	0.0739 (5)
H3	0.1262	0.1138	−0.1327	0.089*
C4	−0.0109 (2)	0.1786 (2)	−0.05531 (7)	0.0580 (4)
C5	−0.1815 (2)	0.1703 (2)	−0.02662 (7)	0.0578 (4)
C6	−0.3351 (2)	0.0955 (2)	−0.05535 (8)	0.0716 (5)
H6	−0.4506	0.0923	−0.0363	0.086*
C7	0.1244 (2)	0.2722 (2)	−0.01510 (7)	0.0614 (4)
C8	−0.1610 (2)	0.2551 (2)	0.03459 (7)	0.0607 (4)
C9	0.2541 (2)	0.4496 (2)	0.09978 (7)	0.0610 (4)
H9	0.3422	0.4266	0.0700	0.073*
C10	0.3099 (2)	0.54030 (19)	0.15573 (7)	0.0557 (4)
C11	0.4953 (2)	0.5961 (2)	0.16350 (8)	0.0700 (5)
H11	0.5798	0.5748	0.1324	0.084*
C12	0.5558 (3)	0.6816 (2)	0.21590 (9)	0.0783 (5)
H12	0.6801	0.7176	0.2204	0.094*
C13	0.4304 (3)	0.7134 (2)	0.26175 (9)	0.0781 (5)
H13	0.4705	0.7720	0.2973	0.094*
C14	0.2476 (3)	0.6602 (2)	0.25587 (8)	0.0741 (5)
H14	0.1648	0.6823	0.2874	0.089*
C15	0.1854 (2)	0.5737 (2)	0.20321 (8)	0.0610 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0731 (8)	0.1092 (11)	0.0704 (7)	−0.0031 (7)	0.0216 (6)	−0.0101 (7)
O4	0.0713 (8)	0.1189 (12)	0.0746 (8)	−0.0043 (7)	0.0206 (6)	−0.0070 (7)
O5	0.0675 (8)	0.1089 (11)	0.0789 (8)	−0.0129 (7)	0.0191 (6)	−0.0184 (7)
N1	0.0613 (8)	0.0631 (9)	0.0498 (7)	0.0052 (6)	0.0078 (6)	0.0018 (7)
N2	0.0640 (9)	0.0584 (9)	0.0550 (8)	0.0062 (7)	0.0045 (6)	0.0027 (6)
C1	0.0967 (14)	0.0658 (13)	0.0705 (11)	0.0020 (10)	−0.0077 (10)	−0.0015 (10)
C2	0.1067 (15)	0.0726 (14)	0.0597 (10)	0.0146 (11)	0.0006 (10)	−0.0049 (9)
C3	0.0871 (12)	0.0750 (13)	0.0606 (10)	0.0132 (10)	0.0139 (9)	0.0029 (9)
C4	0.0706 (10)	0.0528 (10)	0.0510 (8)	0.0114 (8)	0.0071 (7)	0.0108 (8)
C5	0.0692 (10)	0.0525 (10)	0.0520 (8)	0.0090 (8)	0.0047 (7)	0.0111 (7)
C6	0.0745 (11)	0.0693 (12)	0.0711 (11)	0.0009 (9)	0.0043 (9)	0.0073 (10)
C7	0.0654 (10)	0.0640 (12)	0.0558 (9)	0.0106 (9)	0.0127 (8)	0.0093 (8)
C8	0.0641 (10)	0.0632 (12)	0.0556 (9)	0.0072 (8)	0.0105 (8)	0.0083 (8)
C9	0.0626 (10)	0.0622 (11)	0.0589 (9)	0.0106 (8)	0.0100 (7)	0.0092 (8)
C10	0.0587 (9)	0.0502 (10)	0.0581 (9)	0.0058 (7)	0.0031 (7)	0.0097 (7)
C11	0.0626 (11)	0.0696 (13)	0.0781 (11)	0.0025 (9)	0.0079 (8)	0.0107 (10)
C12	0.0713 (11)	0.0699 (13)	0.0928 (14)	−0.0089 (9)	−0.0062 (10)	0.0072 (11)
C13	0.0924 (14)	0.0607 (13)	0.0797 (12)	−0.0031 (10)	−0.0130 (10)	−0.0018 (10)
C14	0.0827 (12)	0.0714 (13)	0.0687 (11)	0.0012 (10)	0.0076 (9)	−0.0059 (10)
C15	0.0612 (10)	0.0568 (11)	0.0653 (10)	0.0005 (8)	0.0048 (8)	0.0043 (8)

Geometric parameters (Å, º) top

O3—C8	1.2041 (17)	C4—C7	1.473 (2)
O4—C7	1.2068 (17)	C5—C6	1.370 (2)
O5—C15	1.3568 (18)	C5—C8	1.479 (2)
O5—H5	0.8200	C6—H6	0.9300
N1—N2	1.3791 (17)	C9—C10	1.445 (2)
N1—C7	1.4044 (19)	C9—H9	0.9300
N1—C8	1.4105 (19)	C10—C11	1.395 (2)
N2—C9	1.2811 (18)	C10—C15	1.399 (2)
C1—C2	1.371 (2)	C11—C12	1.371 (2)
C1—C6	1.386 (2)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.375 (2)
C2—C3	1.384 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.368 (2)
C3—C4	1.377 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.383 (2)
C4—C5	1.381 (2)	C14—H14	0.9300

C15—O5—H5	109.5	N1—C7—C4	105.31 (13)
N2—N1—C7	130.54 (13)	O3—C8—N1	124.36 (15)
N2—N1—C8	117.71 (11)	O3—C8—C5	130.20 (15)
C7—N1—C8	111.74 (13)	N1—C8—C5	105.43 (12)
C9—N2—N1	121.21 (13)	N2—C9—C10	119.96 (14)
C2—C1—C6	120.94 (17)	N2—C9—H9	120.0
C2—C1—H1	119.5	C10—C9—H9	120.0
C6—C1—H1	119.5	C11—C10—C15	118.16 (15)
C1—C2—C3	121.24 (17)	C11—C10—C9	119.24 (15)
C1—C2—H2	119.4	C15—C10—C9	122.60 (14)
C3—C2—H2	119.4	C12—C11—C10	121.56 (16)
C4—C3—C2	117.71 (16)	C12—C11—H11	119.2
C4—C3—H3	121.1	C10—C11—H11	119.2
C2—C3—H3	121.1	C11—C12—C13	119.14 (17)
C3—C4—C5	120.97 (16)	C11—C12—H12	120.4
C3—C4—C7	129.82 (15)	C13—C12—H12	120.4
C5—C4—C7	109.20 (13)	C14—C13—C12	120.96 (18)
C6—C5—C4	121.26 (15)	C14—C13—H13	119.5
C6—C5—C8	130.43 (14)	C12—C13—H13	119.5
C4—C5—C8	108.30 (14)	C13—C14—C15	120.29 (17)
C5—C6—C1	117.88 (16)	C13—C14—H14	119.9
C5—C6—H6	121.1	C15—C14—H14	119.9
C1—C6—H6	121.1	O5—C15—C14	117.54 (14)
O4—C7—N1	125.03 (16)	O5—C15—C10	122.57 (15)
O4—C7—C4	129.65 (15)	C14—C15—C10	119.88 (15)

C7—N1—N2—C9	−5.3 (2)	C7—N1—C8—O3	178.98 (14)
C8—N1—N2—C9	175.89 (14)	N2—N1—C8—C5	178.99 (12)
C6—C1—C2—C3	0.2 (3)	C7—N1—C8—C5	−0.04 (17)
C1—C2—C3—C4	0.1 (3)	C6—C5—C8—O3	3.4 (3)
C2—C3—C4—C5	0.4 (2)	C4—C5—C8—O3	−177.93 (16)
C2—C3—C4—C7	−177.72 (16)	C6—C5—C8—N1	−177.66 (16)
C3—C4—C5—C6	−1.3 (2)	C4—C5—C8—N1	1.02 (17)
C7—C4—C5—C6	177.25 (15)	N1—N2—C9—C10	−179.69 (13)
C3—C4—C5—C8	179.92 (15)	N2—C9—C10—C11	−178.34 (14)
C7—C4—C5—C8	−1.58 (17)	N2—C9—C10—C15	2.3 (2)
C4—C5—C6—C1	1.5 (2)	C15—C10—C11—C12	−0.1 (2)
C8—C5—C6—C1	−179.97 (16)	C9—C10—C11—C12	−179.50 (15)
C2—C1—C6—C5	−1.0 (3)	C10—C11—C12—C13	−0.2 (3)
N2—N1—C7—O4	−1.0 (3)	C11—C12—C13—C14	0.4 (3)
C8—N1—C7—O4	177.88 (15)	C12—C13—C14—C15	−0.3 (3)
N2—N1—C7—C4	−179.74 (14)	C13—C14—C15—O5	−179.50 (15)
C8—N1—C7—C4	−0.87 (17)	C13—C14—C15—C10	0.0 (3)
C3—C4—C7—O4	1.2 (3)	C11—C10—C15—O5	179.69 (14)
C5—C4—C7—O4	−177.15 (17)	C9—C10—C15—O5	−0.9 (2)
C3—C4—C7—N1	179.85 (16)	C11—C10—C15—C14	0.2 (2)
C5—C4—C7—N1	1.52 (17)	C9—C10—C15—C14	179.56 (15)
N2—N1—C8—O3	−2.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	1.90	2.6152 (16)	145
C9—H9···O4	0.93	2.24	2.8937 (19)	127

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀N₂O₃
M_r	266.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.0877 (2), 8.2400 (4), 21.2752 (7)
β (°)	92.659 (3)
V (Å³)	1241.19 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	11806, 2184, 1541
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.10
No. of reflections	2184
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.11

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	1.90	2.6152 (16)	145
C9—H9···O4	0.93	2.24	2.8937 (19)	127

Acknowledgements

The authors thank Professor T. N. Guru Row and Mr Venkatesha R. Hathwar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection and the UGC-MRP(S) – 541/09 – 10/KAMY002/UGC/SWRO dated 8.1.2010 for financial assistance.

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