2-(Piperidin-1-yl)-6-(1H-pyrrol-1-yl)pyridine-3,5-dicarbonitrile

Horton, P.N.; Mohamed, S.K.; Soliman, A.M.; Abdel-Raheem, E.M.M.; Akkurt, M.

doi:10.1107/S1600536812008586

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o938

doi:10.1107/S1600536812008586

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2-(Piperidin-1-yl)-6-(1H-pyrrol-1-yl)pyridine-3,5-dicarbonitrile

Peter N. Horton,^a Shaaban K. Mohamed,^b Ahmed M. Soliman,^c Eman M. M. Abdel-Raheem ^c and Mehmet Akkurt ^d ^*

^aSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, ^bChemistry and Environmental Science Division, School of Science, Manchester Metropolitan University, England, ^cDepartment of Chemistry, Faculty of Science, Sohag University, Sohag, Egypt, and ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 22 February 2012; accepted 26 February 2012; online 3 March 2012)

The piperidine ring of the title compound, C₁₆H₁₅N₅, adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.035 (3) Å. The pyrrole and pyridine rings are almost coplanar, forming a dihedral angle of 3.48 (14)°. In the crystal, no classical hydrogen bonds were found. In the crystal, the molecules are linked by aromatic π–π stacking [centroid–centroid separations = 3.4984 (16) and 3.9641 (15) Å between pyrrole and pyridine rings and between pyridine rings, respectively].

Related literature

For the biological activity of cyano-amino pyridines, see: Al-Haiza et al. (2003 ); Bhalerao & Krishnaiah (1995 ); Doe et al. (1990 ); Murata et al. (2003 ); Shankaraiah et al. (2010 ); Shishoo et al. (1983 ); Soliman et al. (2012 ); Temple et al. (1992 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₁₅N₅
M_r = 277.33
Monoclinic, P 2₁ /c
a = 11.9372 (16) Å
b = 6.6919 (8) Å
c = 17.158 (2) Å
β = 92.280 (7)°
V = 1369.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.32 × 0.04 × 0.02 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ) T_min = 0.973, T_max = 0.998
7877 measured reflections
3098 independent reflections
1503 reflections with I > 2σ(I)
R_int = 0.095

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.140
S = 0.96
3098 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SIR2004 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008586/xu5473sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008586/xu5473Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008586/xu5473Isup3.cml

checkCIF report

Comment top

Among the wide variety of active heterocycles, cyano-amino pyridines have showed important and useful intermediates in preparing variety of heterocyclic compounds (Shishoo et al., 1983; Doe et al., 1990; Bhalerao & Krishnaiah, 1995; Al-Haiza et al., 2003). In addition to this, many naturally occurring and synthetic compounds containing the pyridine scaffold possess interesting pharmacological properties (Temple et al., 1992). Among them, 2-amino-3-cyanopyridines have been identified as IKK-β inhibitors (Murata et al., 2003) and as antibacterial (Shankaraiah et al., 2010). Therefore, the synthesis of 2-amino-3-cyanopyridine derivatives continues to attract much interest in organic chemistry. In this respect, and also in continuation of our earlier work on synthesis of different heterocyclic system that containing highly biological activity (Soliman et al., 2012), we prompted to prepare the new title compound (I) with potential biological activity.

Fig. 1 shows the molecule of (I) which has an open conformation. The N3/C12–C16 piperidine ring adopts a chair conformation [puckering parameters (Cremer & Pople, 1975): Q_T = 0.574 (3) Å, θ = 179.5 (3) ° and φ = 137 (13) °]. The N1/C1–C5 pyridine ring is essentially planar with a maximum deviation of -0.035 (3) Å for C5. The N2/C8–C11 pyrrole and pyridine rings are almost co-planar and they make a dihedral angle of 3.48 (14)° with each other.

The structure exists no classic hydrogen bonds. The crystal packing exhibits π—π interactions with centroid—centroid distances: Cg1—Cg2ⁱ = 3.4984 (16) Å and Cg2—Cg2ⁱⁱ = 3.9641 (15) Å [Fig. 2; Cg1 and Cg2 are the centroids of the N2/C8–C11 pyrrole and N1/C1–C5 pyridine rings, respectively. Symmetry codes: (i) 1 - x, 1 - y, -z and (ii) 1 - x, -y, -z].

Related literature top

For the biological activity of cyano-amino pyridines, see: Al-Haiza et al. (2003); Bhalerao & Krishnaiah (1995); Doe et al. (1990); Murata et al. (2003); Shankaraiah et al. (2010); Shishoo et al. (1983); Soliman et al. (2012); Temple et al. (1992). For ring conformations, see: Cremer & Pople (1975).

Experimental top

An equimolar mixture of 2-chloro-6-(1H-pyrrol-1-yl) pyridine-3,5-dicarbonitrile and piperidine in THF/EtOH (1:3) with few drops of TEA was refluxed at 351 K for 2–3 h. The product was obtained on cooling, collected, washed and re-crystallized from ethanol to afford the title compound. 90% yield, m.p. 413 K. Block-like pure crystals of the title compound, suitable for X-ray diffraction, were obtained by slow evaporation of a solution in ethanol for 24 h.

Structure description top

For the biological activity of cyano-amino pyridines, see: Al-Haiza et al. (2003); Bhalerao & Krishnaiah (1995); Doe et al. (1990); Murata et al. (2003); Shankaraiah et al. (2010); Shishoo et al. (1983); Soliman et al. (2012); Temple et al. (1992). For ring conformations, see: Cremer & Pople (1975).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SIR2004 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing of (I) down the b axis. The hydrogen atoms have been omitted for clarity.

2-(Piperidin-1-yl)-6-(1H-pyrrol-1-yl)pyridine-3,5-dicarbonitrile top

Crystal data top

C₁₆H₁₅N₅	F(000) = 584
M_r = 277.33	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4756 reflections
a = 11.9372 (16) Å	θ = 3.3–27.5°
b = 6.6919 (8) Å	µ = 0.09 mm⁻¹
c = 17.158 (2) Å	T = 100 K
β = 92.280 (7)°	Lath, colourless
V = 1369.5 (3) Å³	0.32 × 0.04 × 0.02 mm
Z = 4

Data collection top

Rigaku Saturn724+ diffractometer	3098 independent reflections
Radiation source: Rotating Anode	1503 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.095
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
profile data from ω–scans	h = −15→15
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −7→8
T_min = 0.973, T_max = 0.998	l = −21→22
7877 measured reflections

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0431P)²] where P = (F_o² + 2F_c²)/3
3098 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₅N₅	V = 1369.5 (3) Å³
M_r = 277.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9372 (16) Å	µ = 0.09 mm⁻¹
b = 6.6919 (8) Å	T = 100 K
c = 17.158 (2) Å	0.32 × 0.04 × 0.02 mm
β = 92.280 (7)°

Data collection top

Rigaku Saturn724+ diffractometer	3098 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	1503 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.998	R_int = 0.095
7877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.96	Δρ_max = 0.21 e Å⁻³
3098 reflections	Δρ_min = −0.24 e Å⁻³
190 parameters

Special details top

Experimental. CrystalClear-SM Expert

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
N1	0.57393 (18)	0.2530 (3)	0.06283 (13)	0.0173 (7)
N2	0.38710 (18)	0.2792 (3)	0.03066 (13)	0.0168 (7)
N3	0.75463 (17)	0.2158 (3)	0.11176 (13)	0.0192 (7)
N4	0.3876 (2)	0.2027 (4)	−0.19418 (14)	0.0312 (9)
N5	0.9243 (2)	0.2228 (3)	−0.06919 (14)	0.0262 (8)
C1	0.4966 (2)	0.2520 (4)	0.00532 (16)	0.0169 (9)
C2	0.5227 (2)	0.2225 (4)	−0.07288 (15)	0.0150 (8)
C3	0.6365 (2)	0.2034 (4)	−0.08826 (15)	0.0180 (9)
C4	0.7185 (2)	0.2039 (4)	−0.02904 (15)	0.0167 (9)
C5	0.6829 (2)	0.2212 (4)	0.04902 (15)	0.0153 (8)
C6	0.4457 (2)	0.2118 (4)	−0.13900 (16)	0.0209 (9)
C7	0.8327 (2)	0.2111 (4)	−0.05098 (15)	0.0174 (9)
C8	0.2865 (2)	0.2905 (4)	−0.01382 (17)	0.0207 (9)
C9	0.2014 (2)	0.3079 (4)	0.03534 (16)	0.0206 (9)
C10	0.2483 (2)	0.3078 (4)	0.11287 (16)	0.0199 (9)
C11	0.3609 (2)	0.2903 (4)	0.10890 (16)	0.0191 (9)
C12	0.7216 (2)	0.2875 (4)	0.18847 (16)	0.0250 (9)
C13	0.8159 (2)	0.4145 (4)	0.22429 (17)	0.0255 (10)
C14	0.9264 (2)	0.3013 (4)	0.22895 (17)	0.0263 (10)
C15	0.9552 (2)	0.2224 (4)	0.14853 (17)	0.0233 (9)
C16	0.8582 (2)	0.0981 (4)	0.11522 (16)	0.0212 (9)
H3	0.65750	0.19000	−0.13960	0.0220*
H8	0.27940	0.28670	−0.06800	0.0250*
H9	0.12570	0.31800	0.02100	0.0250*
H10	0.20860	0.31800	0.15830	0.0240*
H11	0.41200	0.28630	0.15120	0.0230*
H12A	0.70700	0.17480	0.22220	0.0300*
H12B	0.65350	0.36630	0.18270	0.0300*
H13A	0.79650	0.45540	0.27630	0.0310*
H13B	0.82440	0.53410	0.19310	0.0310*
H14A	0.92100	0.19040	0.26500	0.0320*
H14B	0.98570	0.38940	0.24850	0.0320*
H15A	0.96940	0.33340	0.11390	0.0280*
H15B	1.02240	0.14110	0.15290	0.0280*
H16A	0.87490	0.05300	0.06320	0.0250*
H16B	0.84820	−0.01880	0.14760	0.0250*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0151 (12)	0.0199 (13)	0.0168 (13)	−0.0004 (10)	−0.0007 (10)	0.0011 (10)
N2	0.0133 (11)	0.0187 (12)	0.0183 (13)	0.0017 (10)	0.0011 (9)	−0.0014 (10)
N3	0.0146 (12)	0.0250 (13)	0.0179 (13)	0.0045 (10)	0.0004 (10)	−0.0054 (11)
N4	0.0255 (14)	0.0450 (17)	0.0230 (15)	0.0032 (13)	−0.0010 (12)	−0.0044 (13)
N5	0.0203 (14)	0.0315 (15)	0.0267 (15)	0.0043 (12)	0.0014 (11)	−0.0003 (12)
C1	0.0169 (14)	0.0124 (15)	0.0213 (16)	−0.0017 (11)	0.0012 (12)	0.0013 (11)
C2	0.0158 (14)	0.0143 (15)	0.0146 (14)	−0.0008 (12)	−0.0030 (11)	0.0021 (11)
C3	0.0235 (15)	0.0159 (15)	0.0149 (15)	−0.0011 (13)	0.0049 (12)	−0.0010 (12)
C4	0.0178 (15)	0.0158 (15)	0.0166 (15)	−0.0001 (13)	0.0006 (12)	0.0003 (12)
C5	0.0144 (14)	0.0155 (15)	0.0161 (15)	−0.0038 (12)	0.0009 (11)	−0.0011 (11)
C6	0.0185 (15)	0.0262 (16)	0.0183 (15)	0.0012 (13)	0.0038 (13)	0.0002 (13)
C7	0.0212 (15)	0.0182 (15)	0.0126 (15)	0.0034 (13)	−0.0012 (12)	0.0007 (12)
C8	0.0187 (15)	0.0206 (16)	0.0227 (16)	0.0008 (13)	−0.0016 (12)	0.0012 (13)
C9	0.0162 (15)	0.0227 (16)	0.0229 (17)	−0.0004 (13)	0.0025 (12)	−0.0010 (13)
C10	0.0185 (15)	0.0186 (16)	0.0231 (16)	−0.0027 (12)	0.0065 (12)	0.0003 (13)
C11	0.0198 (15)	0.0214 (15)	0.0160 (15)	−0.0013 (13)	0.0003 (12)	−0.0010 (13)
C12	0.0184 (15)	0.0321 (17)	0.0243 (17)	−0.0003 (14)	0.0000 (12)	−0.0095 (14)
C13	0.0227 (17)	0.0302 (18)	0.0233 (17)	0.0015 (14)	−0.0017 (13)	−0.0052 (14)
C14	0.0215 (16)	0.0304 (18)	0.0268 (17)	−0.0030 (14)	−0.0022 (13)	−0.0068 (15)
C15	0.0157 (15)	0.0266 (17)	0.0278 (17)	−0.0013 (13)	0.0019 (12)	−0.0004 (14)
C16	0.0186 (15)	0.0251 (16)	0.0199 (17)	0.0039 (13)	0.0016 (13)	−0.0002 (12)

Geometric parameters (Å, º) top

N1—C1	1.324 (3)	C12—C13	1.521 (4)
N1—C5	1.348 (3)	C13—C14	1.520 (3)
N2—C1	1.406 (3)	C14—C15	1.529 (4)
N2—C8	1.399 (3)	C15—C16	1.519 (4)
N2—C11	1.392 (4)	C3—H3	0.9300
N3—C5	1.349 (3)	C8—H8	0.9300
N3—C12	1.470 (3)	C9—H9	0.9300
N3—C16	1.465 (3)	C10—H10	0.9300
N4—C6	1.153 (4)	C11—H11	0.9300
N5—C7	1.152 (3)	C12—H12A	0.9700
C1—C2	1.403 (4)	C12—H12B	0.9700
C2—C3	1.400 (3)	C13—H13A	0.9700
C2—C6	1.433 (4)	C13—H13B	0.9700
C3—C4	1.383 (4)	C14—H14A	0.9700
C4—C5	1.426 (4)	C14—H14B	0.9700
C4—C7	1.429 (3)	C15—H15A	0.9700
C8—C9	1.351 (4)	C15—H15B	0.9700
C9—C10	1.423 (4)	C16—H16A	0.9700
C10—C11	1.354 (3)	C16—H16B	0.9700

C1—N1—C5	121.1 (2)	N2—C8—H8	126.00
C1—N2—C8	128.8 (2)	C9—C8—H8	126.00
C1—N2—C11	123.5 (2)	C8—C9—H9	126.00
C8—N2—C11	107.6 (2)	C10—C9—H9	126.00
C5—N3—C12	121.4 (2)	C9—C10—H10	126.00
C5—N3—C16	123.7 (2)	C11—C10—H10	126.00
C12—N3—C16	113.3 (2)	N2—C11—H11	126.00
N1—C1—N2	113.5 (2)	C10—C11—H11	126.00
N1—C1—C2	122.6 (2)	N3—C12—H12A	110.00
N2—C1—C2	124.0 (2)	N3—C12—H12B	110.00
C1—C2—C3	116.6 (2)	C13—C12—H12A	110.00
C1—C2—C6	127.2 (2)	C13—C12—H12B	110.00
C3—C2—C6	116.3 (2)	H12A—C12—H12B	108.00
C2—C3—C4	121.7 (2)	C12—C13—H13A	109.00
C3—C4—C5	117.5 (2)	C12—C13—H13B	109.00
C3—C4—C7	117.5 (2)	C14—C13—H13A	109.00
C5—C4—C7	124.6 (2)	C14—C13—H13B	109.00
N1—C5—N3	116.8 (2)	H13A—C13—H13B	108.00
N1—C5—C4	120.2 (2)	C13—C14—H14A	110.00
N3—C5—C4	123.0 (2)	C13—C14—H14B	110.00
N4—C6—C2	177.1 (3)	C15—C14—H14A	110.00
N5—C7—C4	178.0 (3)	C15—C14—H14B	110.00
N2—C8—C9	108.3 (2)	H14A—C14—H14B	108.00
C8—C9—C10	107.8 (2)	C14—C15—H15A	110.00
C9—C10—C11	107.9 (2)	C14—C15—H15B	110.00
N2—C11—C10	108.3 (2)	C16—C15—H15A	110.00
N3—C12—C13	108.9 (2)	C16—C15—H15B	110.00
C12—C13—C14	111.7 (2)	H15A—C15—H15B	108.00
C13—C14—C15	110.5 (2)	N3—C16—H16A	110.00
C14—C15—C16	109.5 (2)	N3—C16—H16B	110.00
N3—C16—C15	110.5 (2)	C15—C16—H16A	110.00
C2—C3—H3	119.00	C15—C16—H16B	110.00
C4—C3—H3	119.00	H16A—C16—H16B	108.00

C5—N1—C1—N2	177.4 (2)	N2—C1—C2—C3	178.3 (2)
C5—N1—C1—C2	−1.4 (4)	N2—C1—C2—C6	−1.0 (4)
C1—N1—C5—N3	−177.0 (2)	N1—C1—C2—C6	177.7 (3)
C1—N1—C5—C4	5.8 (4)	N1—C1—C2—C3	−3.0 (4)
C8—N2—C1—N1	178.4 (2)	C1—C2—C3—C4	3.0 (4)
C11—N2—C1—C2	174.0 (2)	C6—C2—C3—C4	−177.6 (3)
C1—N2—C8—C9	177.1 (2)	C2—C3—C4—C7	−171.7 (3)
C1—N2—C11—C10	−177.3 (2)	C2—C3—C4—C5	1.1 (4)
C8—N2—C11—C10	0.0 (3)	C3—C4—C5—N1	−5.5 (4)
C8—N2—C1—C2	−2.8 (4)	C7—C4—C5—N3	−10.5 (4)
C11—N2—C8—C9	0.0 (3)	C3—C4—C5—N3	177.4 (2)
C11—N2—C1—N1	−4.8 (3)	C7—C4—C5—N1	166.6 (2)
C5—N3—C16—C15	134.0 (2)	N2—C8—C9—C10	0.0 (3)
C12—N3—C5—N1	−14.1 (3)	C8—C9—C10—C11	0.0 (3)
C12—N3—C16—C15	−60.3 (3)	C9—C10—C11—N2	0.0 (3)
C16—N3—C5—C4	−32.4 (4)	N3—C12—C13—C14	−55.5 (3)
C5—N3—C12—C13	−135.4 (2)	C12—C13—C14—C15	55.1 (3)
C16—N3—C12—C13	58.5 (3)	C13—C14—C15—C16	−54.7 (3)
C16—N3—C5—N1	150.5 (2)	C14—C15—C16—N3	56.7 (3)
C12—N3—C5—C4	163.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···N1	0.97	2.36	2.740 (3)	103

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₅
M_r	277.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.9372 (16), 6.6919 (8), 17.158 (2)
β (°)	92.280 (7)
V (Å³)	1369.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.04 × 0.02

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2011)
T_min, T_max	0.973, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	7877, 3098, 1503
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.140, 0.96
No. of reflections	3098
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.24

Computer programs: CrystalClear-SM Expert (Rigaku, 2011), SIR2004 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Acknowledgements

The EPSRC National Crystallography Service is gratefully acknowledged for the X-ray diffraction measurements. The authors are thankful to Manchester Metropolitan University and Sohag University for supporting this study.

References

Al-Haiza, M. A., Mostafa, M. S. & El-Kady, M. Y. (2003). Molecules, 8, 275–286. CAS Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bhalerao, U. T. & Krishnaiah, A. (1995). Indian J. Chem. Sect. B, 34, 587–590. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Doe, K., Avasthi, K., Pratap, R., Bakuni, D. S. & Joshi, M. N. (1990). Indian J. Chem. Sect B, 29, 459–463. 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
Murata, T., Shimada, M., Sakakibara, S., Yoshino, T., Kadono, H., Masuda, T., Shimazaki, M., Shintani, T., Fuchikami, K., Sakai, K., Inbe, H., Takeshita, K., Niki, T., Umeda, M., Bacon, K. B., Ziegelbauer, K. B. & Lowinger, T. B. (2003). Bioorg. Med. Chem. Lett. 13, 913–918. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Shankaraiah, G. K., Vishnu, T. K. & Bhaskar, S. D. (2010). J. Chem. Pharm. Res. 2, 187–191. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shishoo, C. J., Devani, M. B., Bhadti, V. C., Ananthan, S. & Ullas, G. V. (1983). Tetrahedron Lett. 24, 4611–4612. CrossRef CAS Web of Science Google Scholar
Soliman, A. M., Mohamed, S. K., El Remail, M. A. & Abdel Ghany, H. (2012). Eur. J. Med. Chem. 47, 138–142. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Temple, C., Rener, G. A., Raud, W. R. & Noker, P. E. (1992). J. Med. Chem. 35, 3686–3690. CrossRef PubMed CAS Web of Science Google Scholar