Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages o812-o813
https://doi.org/10.1107/S1600536814014354

2,6-Di­amino-4-(4-chloro­phen­yl)-1-methyl-1,4-di­hydro­pyridine-3,5-dicarbo­nitrile

Michael Purushothaman,a* Kaliyaperumal Thanigaimani,b Suhana Arshad,b Sekar Silambarasan,a Ibrahim Abdul Razakb‡ and Kather Mohideen Sithick Alia

aDepartment of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli 620 020, Tamil Nadu, India, and bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: purush.alpha@gmail.com

(Received 10 June 2014; accepted 18 June 2014; online 25 June 2014)

In the title compound, C14H12ClN5, the di­hydro­pyridine ring adopts a shallow boat conformation. The dihedral angle between the plane of this ring and that of the chloro­benzene ring is 69.15 (15)°. In the crystal, mol­ecules are linked by N—H⋯N and N—H⋯Cl hydrogen bonds, generating (001) sheets.

Keywords: crystal structure.

CCDC reference: 1009061

Similar articles

Related literature

For background to malono­nitrile, see: Fatiadi (1978[Fatiadi, A. J. (1978). Synthesis, 3, 165-204.]); Raghukumar et al. (2003[Raghukumar, V., Thiirumalai, D., Ramakrishnan, V., Karunakara, V. & Ramamurthy, P. (2003). Tetrahedron, 59, 3761-3768.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12ClN5

  • Mr = 285.74

  • Triclinic, [P \overline 1]

  • a = 8.3893 (4) Å

  • b = 8.4679 (5) Å

  • c = 10.2571 (6) Å

  • α = 93.148 (4)°

  • β = 112.478 (3)°

  • γ = 93.929 (3)°

  • V = 669.11 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 100 K

  • 0.37 × 0.28 × 0.16 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.904, Tmax = 0.956

  • 9775 measured reflections

  • 3049 independent reflections

  • 2435 reflections with I > 2σ(I)

  • Rint = 0.053
Refinement

  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 0.207

  • S = 1.05

  • 3049 reflections

  • 198 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.17 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H1N2⋯N5i 0.86 (5) 2.21 (5) 3.043 (4) 163 (5)
N2—H2N2⋯Cl1ii 0.89 (4) 2.75 (4) 3.588 (3) 158 (3)
N3—H2N3⋯N4iii 0.83 (4) 2.27 (4) 3.071 (4) 161 (4)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1009061

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814014354/hb7240sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814014354/hb7240Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814014354/hb7240Isup3.cml

checkCIF report


Comment top

Malononitrile is a simple and versatile reagent for the synthesis of heterocyclic compounds and precursors of novel compounds. It exhibits a unique reactivity due to the strong electron withdrawing cycano groups to activate the methylene group and the polar multiple bond suitable for nucleophilic addition (Fatiadi, 1978). Malononitrile is used as reactant or reaction intermediate in various multicomponent reactions to prepare heterocyclic compounds. The three component reactions of malononitrile, aldehyde and amine show very chemical diversity, from which several kinds of products were separated (Raghukumar et al., 2003). The crystal structure of the title compound (I) is presented here.

The molecular structure of the title compound is shown in Fig. 1. The pyridine ring (N1/C7—C11) adopts a boat conformation with puckering parameters Q= 0.402 (3) Å, Θ= 79.6 (4)° and Φ= 177.2 (4)°. The dihedral angle between the pyridine (N1/C7—C11) and benzene (C1—C6) rings is 69.15 (15) °.

The crystal structure shown in Fig. 2 features N2—H1N2···N5i and N3—H2N3···N4iii hydrogen bonds (symmetry code in Table 1) to result in tetrameric association of molecules, generated by inversion. These tetramers are then connected via N2—H2N2···Cl1ii hydrogen bond (symmetry code in Table 1), forming a layer parallel to the ab plane.

Related literature top

For background to malononitrile, see: Fatiadi (1978); Raghukumar et al. (2003). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Compound (I) was prepared by the reaction of p-chlorobenzaldehyde (1 mmol), malononitrile (1 mmol) and methylamine (1 mmol) in a mixed solvent of methanol and water (5:1) was stirred at room temperature about an hour. The resulting precipitate was collected by filtration and washed with methanol to afford pure product, m.p: 290 °C. The product was crystallized from methanol solution as colourless plates.

Refinement top

N-bound H atoms were located in a difference Fourier maps and allowed to be refined freely [refined distance: N–H = 0.83 (4)–0.89 (4) Å]. The remaining hydrogen atoms were positioned geometrically [C–H= 0.95 or 0.98 Å] and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(methyl C). A rotating-group model was used for the methyl group.

Structure description top

Malononitrile is a simple and versatile reagent for the synthesis of heterocyclic compounds and precursors of novel compounds. It exhibits a unique reactivity due to the strong electron withdrawing cycano groups to activate the methylene group and the polar multiple bond suitable for nucleophilic addition (Fatiadi, 1978). Malononitrile is used as reactant or reaction intermediate in various multicomponent reactions to prepare heterocyclic compounds. The three component reactions of malononitrile, aldehyde and amine show very chemical diversity, from which several kinds of products were separated (Raghukumar et al., 2003). The crystal structure of the title compound (I) is presented here.

The molecular structure of the title compound is shown in Fig. 1. The pyridine ring (N1/C7—C11) adopts a boat conformation with puckering parameters Q= 0.402 (3) Å, Θ= 79.6 (4)° and Φ= 177.2 (4)°. The dihedral angle between the pyridine (N1/C7—C11) and benzene (C1—C6) rings is 69.15 (15) °.

The crystal structure shown in Fig. 2 features N2—H1N2···N5i and N3—H2N3···N4iii hydrogen bonds (symmetry code in Table 1) to result in tetrameric association of molecules, generated by inversion. These tetramers are then connected via N2—H2N2···Cl1ii hydrogen bond (symmetry code in Table 1), forming a layer parallel to the ab plane.

For background to malononitrile, see: Fatiadi (1978); Raghukumar et al. (2003). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.
2,6-Diamino-4-(4-chlorophenyl)-1-methyl-1,4-dihydropyridine-3,5-dicarbonitrile top
Crystal data top
C14H12ClN5Z = 2
Mr = 285.74F(000) = 296
Triclinic, P1Dx = 1.418 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3893 (4) ÅCell parameters from 4444 reflections
b = 8.4679 (5) Åθ = 2.6–32.3°
c = 10.2571 (6) ŵ = 0.28 mm−1
α = 93.148 (4)°T = 100 K
β = 112.478 (3)°Plate, colourless
γ = 93.929 (3)°0.37 × 0.28 × 0.16 mm
V = 669.11 (6) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3049 independent reflections
Radiation source: fine-focus sealed tube2435 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −10→10
Tmin = 0.904, Tmax = 0.956k = −10→9
9775 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.207H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.1391P)2 + 0.3591P]
where P = (Fo2 + 2Fc2)/3
3049 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 1.17 e Å−3
0 restraintsΔρmin = −0.48 e Å−3
Crystal data top
C14H12ClN5γ = 93.929 (3)°
Mr = 285.74V = 669.11 (6) Å3
Triclinic, P1Z = 2
a = 8.3893 (4) ÅMo Kα radiation
b = 8.4679 (5) ŵ = 0.28 mm−1
c = 10.2571 (6) ÅT = 100 K
α = 93.148 (4)°0.37 × 0.28 × 0.16 mm
β = 112.478 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3049 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2435 reflections with I > 2σ(I)
Tmin = 0.904, Tmax = 0.956Rint = 0.053
9775 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0720 restraints
wR(F2) = 0.207H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 1.17 e Å−3
3049 reflectionsΔρmin = −0.48 e Å−3
198 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
xyzUiso*/Ueq
Cl10.41603 (9)0.41701 (9)−0.28944 (7)0.0186 (3)
N11.1252 (3)0.0360 (3)0.2661 (3)0.0153 (5)
N20.9603 (3)−0.1777 (3)0.3020 (3)0.0164 (5)
N31.3641 (3)0.2241 (3)0.3245 (3)0.0171 (6)
N40.6529 (3)0.0004 (3)0.4178 (3)0.0184 (6)
N51.2267 (3)0.5888 (3)0.4289 (3)0.0198 (6)
C10.8304 (4)0.4173 (4)0.0726 (3)0.0181 (6)
H1A0.94090.47580.11760.022*
C20.7184 (4)0.4557 (4)−0.0597 (3)0.0189 (6)
H2A0.75160.5389−0.10530.023*
C30.5572 (4)0.3693 (4)−0.1231 (3)0.0157 (6)
C40.5057 (4)0.2498 (4)−0.0585 (3)0.0187 (6)
H4A0.39430.1930−0.10310.022*
C50.6194 (4)0.2132 (4)0.0734 (3)0.0182 (6)
H5A0.58440.13080.11880.022*
C60.7834 (3)0.2950 (3)0.1401 (3)0.0136 (6)
C70.9013 (3)0.2604 (3)0.2911 (3)0.0133 (6)
H7A0.86770.32630.35870.016*
C80.8816 (4)0.0898 (3)0.3211 (3)0.0137 (6)
C90.9872 (3)−0.0158 (3)0.2979 (3)0.0110 (6)
C101.1955 (4)0.1912 (3)0.3081 (3)0.0135 (6)
C111.0935 (3)0.3048 (3)0.3278 (3)0.0141 (6)
C120.7568 (4)0.0383 (3)0.3743 (3)0.0153 (6)
C131.2207 (4)−0.0783 (4)0.2184 (3)0.0200 (7)
H13A1.1391−0.16540.15680.030*
H13B1.3055−0.12100.30080.030*
H13C1.2811−0.02450.16570.030*
C141.1690 (4)0.4592 (4)0.3845 (3)0.0145 (6)
H1N21.050 (6)−0.226 (6)0.345 (5)0.043 (12)*
H2N20.873 (5)−0.220 (5)0.322 (4)0.022 (9)*
H1N31.414 (5)0.315 (6)0.355 (4)0.030 (11)*
H2N31.425 (5)0.150 (5)0.355 (4)0.029 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0168 (4)0.0188 (4)0.0178 (4)0.0060 (3)0.0030 (3)0.0034 (3)
N10.0126 (11)0.0132 (12)0.0215 (12)0.0042 (9)0.0080 (10)−0.0010 (10)
N20.0137 (12)0.0082 (12)0.0282 (14)0.0055 (10)0.0084 (11)0.0015 (10)
N30.0126 (12)0.0132 (13)0.0292 (14)0.0081 (11)0.0107 (11)0.0041 (11)
N40.0145 (12)0.0168 (13)0.0261 (14)0.0081 (10)0.0090 (11)0.0030 (11)
N50.0210 (13)0.0136 (13)0.0244 (13)0.0080 (10)0.0074 (11)0.0020 (10)
C10.0150 (13)0.0141 (14)0.0235 (15)0.0024 (11)0.0056 (12)−0.0009 (12)
C20.0189 (14)0.0164 (15)0.0226 (15)0.0036 (12)0.0088 (12)0.0034 (12)
C30.0175 (13)0.0154 (14)0.0153 (13)0.0113 (11)0.0058 (11)0.0010 (11)
C40.0156 (13)0.0162 (15)0.0232 (15)0.0019 (11)0.0062 (12)0.0023 (12)
C50.0178 (14)0.0135 (14)0.0232 (15)0.0020 (11)0.0074 (12)0.0048 (12)
C60.0139 (13)0.0130 (14)0.0168 (13)0.0094 (11)0.0081 (11)0.0002 (11)
C70.0117 (12)0.0118 (14)0.0173 (14)0.0068 (10)0.0057 (11)0.0005 (11)
C80.0131 (12)0.0112 (13)0.0189 (14)0.0056 (11)0.0080 (11)0.0016 (11)
C90.0092 (12)0.0084 (13)0.0146 (13)0.0072 (10)0.0028 (10)−0.0003 (10)
C100.0124 (13)0.0136 (14)0.0160 (13)0.0054 (11)0.0064 (11)0.0022 (11)
C110.0129 (13)0.0131 (14)0.0174 (14)0.0064 (11)0.0065 (11)0.0003 (11)
C120.0151 (13)0.0130 (14)0.0167 (14)0.0091 (11)0.0036 (11)0.0022 (11)
C130.0195 (14)0.0142 (15)0.0297 (17)0.0075 (12)0.0130 (13)−0.0041 (12)
C140.0114 (12)0.0164 (15)0.0160 (13)0.0086 (11)0.0041 (11)0.0032 (11)
Geometric parameters (Å, º) top
Cl1—C31.753 (3)C3—C41.372 (4)
N1—C91.369 (4)C4—C51.391 (4)
N1—C101.378 (4)C4—H4A0.9500
N1—C131.474 (4)C5—C61.392 (4)
N2—C91.379 (4)C5—H5A0.9500
N2—H1N20.86 (5)C6—C71.543 (4)
N2—H2N20.89 (4)C7—C81.505 (4)
N3—C101.366 (4)C7—C111.523 (4)
N3—H1N30.83 (5)C7—H7A1.0000
N3—H2N30.83 (4)C8—C91.373 (4)
N4—C121.155 (4)C8—C121.410 (4)
N5—C141.162 (4)C10—C111.386 (4)
C1—C61.393 (4)C11—C141.403 (4)
C1—C21.395 (4)C13—H13A0.9800
C1—H1A0.9500C13—H13B0.9800
C2—C31.388 (4)C13—H13C0.9800
C2—H2A0.9500
C9—N1—C10118.3 (2)C8—C7—C11107.0 (2)
C9—N1—C13120.6 (2)C8—C7—C6113.9 (2)
C10—N1—C13119.7 (2)C11—C7—C6113.9 (2)
C9—N2—H1N2117 (3)C8—C7—H7A107.2
C9—N2—H2N2121 (3)C11—C7—H7A107.2
H1N2—N2—H2N2108 (4)C6—C7—H7A107.2
C10—N3—H1N3120 (3)C9—C8—C12119.9 (3)
C10—N3—H2N3113 (3)C9—C8—C7119.8 (3)
H1N3—N3—H2N3115 (4)C12—C8—C7120.3 (2)
C6—C1—C2121.3 (3)C8—C9—N1120.7 (3)
C6—C1—H1A119.4C8—C9—N2123.1 (3)
C2—C1—H1A119.4N1—C9—N2116.2 (2)
C3—C2—C1118.4 (3)N3—C10—N1116.7 (3)
C3—C2—H2A120.8N3—C10—C11123.7 (3)
C1—C2—H2A120.8N1—C10—C11119.6 (3)
C4—C3—C2121.8 (3)C10—C11—C14119.7 (3)
C4—C3—Cl1119.6 (2)C10—C11—C7119.9 (3)
C2—C3—Cl1118.5 (2)C14—C11—C7120.4 (2)
C3—C4—C5118.9 (3)N4—C12—C8178.0 (3)
C3—C4—H4A120.5N1—C13—H13A109.5
C5—C4—H4A120.5N1—C13—H13B109.5
C4—C5—C6121.3 (3)H13A—C13—H13B109.5
C4—C5—H5A119.3N1—C13—H13C109.5
C6—C5—H5A119.3H13A—C13—H13C109.5
C1—C6—C5118.2 (3)H13B—C13—H13C109.5
C1—C6—C7121.4 (3)N5—C14—C11177.8 (3)
C5—C6—C7120.1 (3)
C6—C1—C2—C30.3 (5)C7—C8—C9—N18.9 (4)
C1—C2—C3—C40.7 (5)C12—C8—C9—N210.8 (4)
C1—C2—C3—Cl1−180.0 (2)C7—C8—C9—N2−169.8 (3)
C2—C3—C4—C5−0.8 (5)C10—N1—C9—C823.8 (4)
Cl1—C3—C4—C5179.9 (2)C13—N1—C9—C8−169.9 (3)
C3—C4—C5—C6−0.2 (5)C10—N1—C9—N2−157.4 (3)
C2—C1—C6—C5−1.3 (4)C13—N1—C9—N28.9 (4)
C2—C1—C6—C7−175.4 (3)C9—N1—C10—N3156.2 (3)
C4—C5—C6—C11.2 (4)C13—N1—C10—N3−10.2 (4)
C4—C5—C6—C7175.4 (3)C9—N1—C10—C11−25.5 (4)
C1—C6—C7—C8−152.0 (3)C13—N1—C10—C11168.1 (3)
C5—C6—C7—C834.0 (3)N3—C10—C11—C14−8.3 (4)
C1—C6—C7—C11−28.9 (4)N1—C10—C11—C14173.5 (3)
C5—C6—C7—C11157.1 (3)N3—C10—C11—C7173.1 (3)
C11—C7—C8—C9−34.8 (3)N1—C10—C11—C7−5.1 (4)
C6—C7—C8—C992.0 (3)C8—C7—C11—C1032.9 (4)
C11—C7—C8—C12144.5 (3)C6—C7—C11—C10−93.9 (3)
C6—C7—C8—C12−88.7 (3)C8—C7—C11—C14−145.7 (3)
C12—C8—C9—N1−170.4 (3)C6—C7—C11—C1487.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N2···N5i0.86 (5)2.21 (5)3.043 (4)163 (5)
N2—H2N2···Cl1ii0.89 (4)2.75 (4)3.588 (3)158 (3)
N3—H2N3···N4iii0.83 (4)2.27 (4)3.071 (4)161 (4)
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1N2···N5i0.86 (5)2.21 (5)3.043 (4)163 (5)
N2—H2N2···Cl1ii0.89 (4)2.75 (4)3.588 (3)158 (3)
N3—H2N3···N4iii0.83 (4)2.27 (4)3.071 (4)161 (4)
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z; (iii) x+1, y, z.
 

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

KT and IAR thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant, No. 304/PFIZIK/6312078. MP, SS and KMSA thank the Management and the Principal, Jamal Mohamed College (Autonomous), for providing research facilities. MP thanks the UGC–SERO, Hyderabad, for a minor research project. KT thanks The Academy of Sciences for the Developing World and USM for the TWAS–USM fellowship.

References

First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFatiadi, A. J. (1978). Synthesis, 3, 165–204.  CrossRef Google Scholar
 First citationRaghukumar, V., Thiirumalai, D., Ramakrishnan, V., Karunakara, V. & Ramamurthy, P. (2003). Tetrahedron, 59, 3761–3768.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages o812-o813
https://doi.org/10.1107/S1600536814014354
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS