Dimethyl 2-[2-(2,4,6-tri­chloro­phen­yl)hydrazin-1-yl­idene]butane­dioate

Usha, M.K.; Shetty, S.; Kalluraya, B.; Kant, R.; Gupta, V.K.; Revannasiddaiah, D.

doi:10.1107/S160053681303242X

organic compounds

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Volume 70| Part 1| January 2014| Page o13

https://doi.org/10.1107/S160053681303242X

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Dimethyl 2-[2-(2,4,6-trichlorophenyl)hydrazin-1-ylidene]butanedioate

M. K. Usha,^a Shobhitha Shetty,^b B. Kalluraya,^b Rajni Kant,^c Vivek K. Gupta ^c and D. Revannasiddaiah ^a ^*

^aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^cPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: dr@physics.uni-mysore.ac.in

(Received 28 October 2013; accepted 27 November 2013; online 4 December 2013)

In the title compound, C₁₂H₁₁Cl₃N₂O₄, the dihedral angle between the aromatic ring and the hydrazine (NH—N=C) grouping is 52.2 (3)°. The butanedioate groups exhibit planar conformations. An intramolecular N—H⋯O hydrogen bond links the N—H group of the hydrazine to one of the methoxy groups of the butanedioate moiety. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and π–π interactions are also observed [centroid–centroid separation = 3.535 (1) Å].

CCDC reference: 967565

Related literature

For the pharmacological activity of halo-substituted derivatives, see: Kees et al. (1996 ). For the use of the title compound in the synthesis of pyrazoles, see: Palacios et al. (1999 ). For the biological activity of pyrazoles, see: Palacios et al. (1999); Lee et al. (2003 ); Nithinchandra et al. (2012 ); Genin et al. (2000 ); Reddy et al. (2008 ); Kees et al. (1996). For a related structure, see: Huang et al. (2011 ).

Experimental

Crystal data

C₁₂H₁₁Cl₃N₂O₄
M_r = 353.58
Orthorhombic, P b c a
a = 7.0182 (5) Å
b = 16.0165 (12) Å
c = 26.7488 (15) Å
V = 3006.8 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.716, T_max = 1.000
7083 measured reflections
2954 independent reflections
1844 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.118
S = 1.03
2954 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O15	0.87 (3)	2.38 (3)	3.047 (3)	133 (3)
C5—H5⋯O19ⁱ	0.93	2.51	3.397 (4)	159
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 967565

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S160053681303242X/sj5364sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681303242X/sj5364Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681303242X/sj5364Isup3.cml

checkCIF report

Comment top

It has been reported in the literature that halo substituted derivatives possess significant pharmacological activity (Kees et al., 1996). Also the title compound can be used as an intermediate for the synthesis of pyrazoles (Palacios et al., 1999). Aryl pyrazoles have antimicrobial (Palacios et al., 1999, Lee et al., 2003), anti-inflammatory (Nithinchandra et al., 2012) and non-nucleoside HIV-I reverse transcriptase inhibitor activity (Genin et al., 2000). Furthermore, pyrazoles with a wide array of substituted groups were reported to be selective inhibitors of cyclooxygenase (Reddy et al., 2008) and also exhibit antidiabetic properties (Kees et al., 1996).

In the title compound, C₁₂H₁₁C₁₃N₂O₄, the trichlorophenyl ring is planar (r.m.s. deviation 0.018 Å); the largest deviation from the mean plane is 0.02 (3) Å for atom C1. The bond distances in the title compound are comparable to those observed in the closely related structure (E)-benzaldehyde (2,4,6-trichlorophenyl) hydrazone (Huang et al., 2011). The C1—N10—N11—C12 torsion angle of the atoms joining the trichlorophenyl ring and the butanedioate group is 175.9 (3). An intramolecular N10–H10···O15 hydrogen bond links the N–H group of the hydrazine to one of the methoxy groups of the butanedioate moiety. In the crystal, molecules are stacked along the a axis by C5—H5..O19 hydrogen bonds and π–π interactions between adjacent trichlorophenyl rings [centroid–centroid separation = 3.535 (1) Å, interplanar spacing = 3.494 Å, centroid shift = 0.53 Å, symmetry code: -1/2 + x,y,1/2 - z].

Related literature top

For the pharmacological activity of halo-substituted derivatives , see: Kees et al. (1996). For the use of the title compound in the synthesis of pyrazoles, see: Palacios et al. (1999). For the biological activity of pyrazoles, see: Palacios et al. (1999); Lee et al. (2003); Nithinchandra et al. (2012); Genin et al. (2000); Reddy et al. (2008); Kees et al. (1996). For a related structure, see: Huang et al. (2011).

Experimental top

The title compound was prepared by refluxing a mixture of trichlorophenyl hydrazine (0.01 mol) and dimethylacetylene dicarboxylate (0.01 mol) in a 10 ml toluene solution for 4 h. The completion of the reaction was monitored by thin layer chromatography. After completion the solvent was evaporated under reduced pressure and the white solid obtained was recrystallized from ethanol.

Structure description top

For the pharmacological activity of halo-substituted derivatives , see: Kees et al. (1996). For the use of the title compound in the synthesis of pyrazoles, see: Palacios et al. (1999). For the biological activity of pyrazoles, see: Palacios et al. (1999); Lee et al. (2003); Nithinchandra et al. (2012); Genin et al. (2000); Reddy et al. (2008); Kees et al. (1996). For a related structure, see: Huang et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The thermal ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing arrangement of molecules viewed along the a axis.

Dimethyl 2-[2-(2,4,6-trichlorophenyl)hydrazin-1-ylidene]butanedioate top

Crystal data top

C₁₂H₁₁Cl₃N₂O₄	F(000) = 1440
M_r = 353.58	D_x = 1.562 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1944 reflections
a = 7.0182 (5) Å	θ = 3.9–27.4°
b = 16.0165 (12) Å	µ = 0.63 mm⁻¹
c = 26.7488 (15) Å	T = 293 K
V = 3006.8 (4) Å³	Block, white
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2954 independent reflections
Radiation source: fine-focus sealed tube	1844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.9°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −19→11
T_min = 0.716, T_max = 1.000	l = −32→30
7083 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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0358P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.006
2954 reflections	Δρ_max = 0.26 e Å⁻³
195 parameters	Δρ_min = −0.24 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: 0.0029 (4)

Crystal data top

C₁₂H₁₁Cl₃N₂O₄	V = 3006.8 (4) Å³
M_r = 353.58	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.0182 (5) Å	µ = 0.63 mm⁻¹
b = 16.0165 (12) Å	T = 293 K
c = 26.7488 (15) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2954 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	1844 reflections with I > 2σ(I)
T_min = 0.716, T_max = 1.000	R_int = 0.040
7083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.26 e Å⁻³
2954 reflections	Δρ_min = −0.24 e Å⁻³
195 parameters

Special details top

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl7	0.13759 (16)	0.09353 (6)	0.31855 (3)	0.0641 (3)
Cl9	0.09570 (15)	−0.23591 (5)	0.27554 (3)	0.0589 (3)
Cl8	0.16340 (14)	−0.01155 (7)	0.12827 (3)	0.0640 (3)
O21	0.4517 (4)	−0.22006 (15)	0.47244 (7)	0.0604 (7)
N11	0.2602 (4)	−0.14140 (16)	0.36258 (8)	0.0385 (6)
N10	0.1266 (4)	−0.08714 (18)	0.34507 (9)	0.0406 (7)
O19	0.5314 (3)	−0.24056 (15)	0.39230 (8)	0.0572 (7)
O15	0.2372 (4)	0.01540 (15)	0.43653 (8)	0.0582 (7)
C3	0.1464 (4)	0.0307 (2)	0.22574 (11)	0.0443 (8)
H3	0.1510	0.0859	0.2150	0.053*
C12	0.2654 (4)	−0.15507 (19)	0.41006 (10)	0.0385 (8)
C1	0.1339 (4)	−0.0696 (2)	0.29355 (10)	0.0344 (7)
O17	0.2154 (4)	−0.02745 (18)	0.51588 (9)	0.0796 (9)
C6	0.1257 (4)	−0.13302 (19)	0.25794 (11)	0.0385 (8)
C5	0.1340 (4)	−0.1159 (2)	0.20686 (11)	0.0429 (8)
H5	0.1315	−0.1589	0.1835	0.051*
C13	0.1318 (5)	−0.1207 (2)	0.44935 (11)	0.0459 (9)
H13A	0.0081	−0.1111	0.4342	0.055*
H13B	0.1158	−0.1622	0.4754	0.055*
C4	0.1460 (4)	−0.0342 (2)	0.19178 (12)	0.0459 (9)
C2	0.1399 (4)	0.0117 (2)	0.27610 (11)	0.0401 (8)
C18	0.4236 (5)	−0.2085 (2)	0.42838 (12)	0.0437 (8)
C14	0.1996 (5)	−0.0411 (2)	0.47251 (12)	0.0508 (9)
C16	0.3100 (6)	0.0954 (2)	0.45282 (14)	0.0744 (12)
H16A	0.3322	0.1303	0.4242	0.112*
H16B	0.4275	0.0874	0.4706	0.112*
H16C	0.2187	0.1217	0.4744	0.112*
C20	0.6937 (6)	−0.2892 (3)	0.40768 (13)	0.0762 (13)
H20A	0.7602	−0.3090	0.3787	0.114*
H20B	0.6515	−0.3358	0.4273	0.114*
H20C	0.7775	−0.2550	0.4273	0.114*
H10	0.096 (5)	−0.044 (2)	0.3640 (11)	0.050 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl7	0.0891 (8)	0.0417 (5)	0.0615 (6)	−0.0035 (5)	0.0025 (5)	−0.0015 (4)
Cl9	0.0786 (7)	0.0401 (5)	0.0580 (6)	−0.0024 (5)	−0.0102 (4)	0.0033 (4)
Cl8	0.0631 (6)	0.0898 (8)	0.0393 (5)	−0.0039 (6)	−0.0063 (4)	0.0186 (5)
O21	0.0808 (18)	0.0676 (18)	0.0327 (13)	0.0156 (15)	−0.0090 (12)	0.0032 (11)
N11	0.0441 (16)	0.0355 (15)	0.0359 (14)	0.0012 (13)	−0.0024 (11)	0.0004 (12)
N10	0.0456 (16)	0.0408 (16)	0.0353 (16)	0.0085 (14)	0.0012 (12)	0.0040 (14)
O19	0.0691 (16)	0.0619 (17)	0.0406 (13)	0.0275 (14)	0.0008 (12)	0.0060 (11)
O15	0.0717 (18)	0.0510 (16)	0.0519 (14)	−0.0054 (14)	0.0097 (13)	−0.0132 (12)
C3	0.0340 (17)	0.050 (2)	0.049 (2)	−0.0022 (17)	−0.0002 (14)	0.0149 (18)
C12	0.0480 (19)	0.0361 (18)	0.0314 (16)	−0.0027 (16)	−0.0009 (13)	0.0017 (13)
C1	0.0289 (16)	0.0398 (19)	0.0344 (17)	0.0020 (15)	0.0001 (12)	0.0065 (14)
O17	0.109 (2)	0.090 (2)	0.0399 (14)	0.018 (2)	−0.0080 (14)	−0.0129 (15)
C6	0.0330 (16)	0.0365 (19)	0.0461 (19)	0.0000 (15)	−0.0038 (14)	0.0096 (15)
C5	0.0390 (18)	0.055 (2)	0.0346 (18)	0.0054 (18)	−0.0061 (14)	−0.0010 (16)
C13	0.055 (2)	0.050 (2)	0.0328 (17)	0.0003 (18)	0.0049 (14)	−0.0002 (16)
C4	0.0306 (17)	0.060 (2)	0.0470 (19)	−0.0008 (18)	−0.0043 (14)	0.0105 (19)
C2	0.0366 (17)	0.0421 (19)	0.0415 (19)	−0.0009 (16)	0.0009 (14)	0.0031 (15)
C18	0.058 (2)	0.0343 (18)	0.0390 (19)	−0.0038 (17)	−0.0011 (16)	−0.0001 (15)
C14	0.049 (2)	0.062 (2)	0.041 (2)	0.014 (2)	0.0062 (16)	−0.0017 (18)
C16	0.091 (3)	0.045 (2)	0.087 (3)	0.000 (2)	0.001 (2)	−0.016 (2)
C20	0.081 (3)	0.081 (3)	0.067 (3)	0.043 (3)	−0.002 (2)	0.008 (2)

Geometric parameters (Å, º) top

Cl7—C2	1.735 (3)	C12—C13	1.512 (4)
Cl9—C6	1.727 (3)	C1—C2	1.383 (4)
Cl8—C4	1.741 (3)	C1—C6	1.394 (4)
O21—C18	1.209 (3)	O17—C14	1.186 (3)
N11—C12	1.289 (3)	C6—C5	1.395 (4)
N11—N10	1.362 (3)	C5—C4	1.372 (5)
N10—C1	1.407 (4)	C5—H5	0.9300
N10—H10	0.88 (3)	C13—C14	1.495 (5)
O19—C18	1.329 (4)	C13—H13A	0.9700
O19—C20	1.440 (4)	C13—H13B	0.9700
O15—C14	1.348 (4)	C16—H16A	0.9600
O15—C16	1.447 (4)	C16—H16B	0.9600
C3—C2	1.382 (4)	C16—H16C	0.9600
C3—C4	1.380 (5)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C12—C18	1.485 (4)	C20—H20C	0.9600

C12—N11—N10	117.8 (3)	H13A—C13—H13B	107.7
N11—N10—C1	116.1 (2)	C5—C4—C3	121.7 (3)
N11—N10—H10	118 (2)	C5—C4—Cl8	119.3 (3)
C1—N10—H10	115 (2)	C3—C4—Cl8	119.0 (3)
C18—O19—C20	116.9 (3)	C3—C2—C1	122.5 (3)
C14—O15—C16	116.7 (3)	C3—C2—Cl7	118.1 (3)
C2—C3—C4	118.4 (3)	C1—C2—Cl7	119.3 (2)
C2—C3—H3	120.8	O21—C18—O19	123.7 (3)
C4—C3—H3	120.8	O21—C18—C12	122.2 (3)
N11—C12—C18	116.4 (3)	O19—C18—C12	114.1 (3)
N11—C12—C13	127.3 (3)	O17—C14—O15	123.8 (4)
C18—C12—C13	116.3 (3)	O17—C14—C13	126.4 (4)
C2—C1—C6	117.1 (3)	O15—C14—C13	109.8 (3)
C2—C1—N10	121.3 (3)	O15—C16—H16A	109.5
C6—C1—N10	121.5 (3)	O15—C16—H16B	109.5
C1—C6—C5	121.6 (3)	H16A—C16—H16B	109.5
C1—C6—Cl9	120.9 (2)	O15—C16—H16C	109.5
C5—C6—Cl9	117.4 (3)	H16A—C16—H16C	109.5
C4—C5—C6	118.5 (3)	H16B—C16—H16C	109.5
C4—C5—H5	120.7	O19—C20—H20A	109.5
C6—C5—H5	120.7	O19—C20—H20B	109.5
C14—C13—C12	113.6 (3)	H20A—C20—H20B	109.5
C14—C13—H13A	108.8	O19—C20—H20C	109.5
C12—C13—H13A	108.8	H20A—C20—H20C	109.5
C14—C13—H13B	108.8	H20B—C20—H20C	109.5
C12—C13—H13B	108.8

C12—N11—N10—C1	175.9 (3)	C4—C3—C2—C1	0.3 (5)
N10—N11—C12—C18	−174.7 (3)	C4—C3—C2—Cl7	−179.3 (2)
N10—N11—C12—C13	3.4 (5)	C6—C1—C2—C3	−2.9 (5)
N11—N10—C1—C2	−127.5 (3)	N10—C1—C2—C3	−179.8 (3)
N11—N10—C1—C6	55.8 (4)	C6—C1—C2—Cl7	176.7 (2)
C2—C1—C6—C5	3.5 (4)	N10—C1—C2—Cl7	−0.2 (4)
N10—C1—C6—C5	−179.6 (3)	C20—O19—C18—O21	−2.2 (5)
C2—C1—C6—Cl9	−174.0 (2)	C20—O19—C18—C12	176.6 (3)
N10—C1—C6—Cl9	2.9 (4)	N11—C12—C18—O21	173.9 (3)
C1—C6—C5—C4	−1.6 (4)	C13—C12—C18—O21	−4.3 (5)
Cl9—C6—C5—C4	176.0 (2)	N11—C12—C18—O19	−4.9 (4)
N11—C12—C13—C14	−92.3 (4)	C13—C12—C18—O19	176.8 (3)
C18—C12—C13—C14	85.7 (4)	C16—O15—C14—O17	3.2 (5)
C6—C5—C4—C3	−1.2 (5)	C16—O15—C14—C13	−178.2 (3)
C6—C5—C4—Cl8	178.2 (2)	C12—C13—C14—O17	−127.7 (4)
C2—C3—C4—C5	1.8 (5)	C12—C13—C14—O15	53.8 (4)
C2—C3—C4—Cl8	−177.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O15	0.87 (3)	2.38 (3)	3.047 (3)	133 (3)
C5—H5···O19ⁱ	0.93	2.51	3.397 (4)	159

Symmetry code: (i) x−1/2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O15	0.87 (3)	2.38 (3)	3.047 (3)	133 (3)
C5—H5···O19ⁱ	0.93	2.51	3.397 (4)	159

Symmetry code: (i) x−1/2, y, −z+1/2.

Acknowledgements

MKU thanks the Department of Science & Technology (DST), New Delhi, for the award of an INSPIRE Fellowship. DR acknowledges the UGC for financial support under the Major Research Project scheme [No. F.41–882/2012 (SR)]. RK acknowledges the DST, New Delhi, for the single-crystal X-ray diffractometer sanctioned as a National Facility.

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