N,N′-Bis(pyrimidin-2-yl)terephthalamide dihydrate

Chantrapromma, S.; Fun, H.-K.; Jana, S.; Hazra, A.; Goswami, S.

doi:10.1107/S1600536807065683

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages o267-o268

https://doi.org/10.1107/S1600536807065683

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N,N′-Bis(pyrimidin-2-yl)terephthalamide dihydrate¹

Suchada Chantrapromma,^a ‡ Hoong-Kun Fun,^b ^* Subrata Jana,^c Anita Hazra ^c and Shyamaprosad Goswami ^c

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 27 November 2007; accepted 5 December 2007; online 12 December 2007)

This manuscript is dedicated to His Majesty Thai King Bhumibol Adulyadej on the occasion of His Majesty's 80th Birthday on 5 December 2007.

The organic molecule of the title compound, C₁₆H₁₂N₆O₂·2H₂O, lies across a crystallographic inversion centre. The dihedral angle between the pyrimidine and benzene rings is 80.78 (6)°. The two pyrimidine rings are parallel by virtue of the centre of symmetry. The pyrimidine and benzene rings form dihedral angles of 41.41 (7) and 40.26 (7)°, respectively, with the amide plane. The molecules are linked by N—H⋯N and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the (1 $[\overline{1}]$ 1) plane. O—H⋯O and C—H⋯O hydrogen bonds involving the water molecules link the adjacent layers into a three-dimensional network. In addition, a C—H⋯π interaction involving the benzene ring is observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related literature on supramolecular chemistry, see: Desiraju (1989 ); Lehn (1995 ). For related structures, see: Goswami, Jana, Das et al. (2007 ); Goswami, Jana, Hazra et al. (2007 ). For related literature on the coordination chemistry and applications of aminopyrimidine derivatives, see: Aakeroy et al. (2006 ); Etter (1990 ); Fun et al. (2006 ); Gallagher et al. (2004 ); Goswami & Mahapatra (1999 ); Smith et al. (1998 ); Wang et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₂N₆O₂·2H₂O
M_r = 356.35
Triclinic, $[P \overline 1]$
a = 5.0733 (1) Å
b = 8.3233 (1) Å
c = 9.9622 (2) Å
α = 68.220 (1)°
β = 75.441 (1)°
γ = 82.333 (1)°
V = 377.72 (1) Å³
Z = 1
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100.0 (1) K
0.33 × 0.22 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.963, T_max = 0.991
12751 measured reflections
2202 independent reflections
1982 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.106
S = 1.12
2202 reflections
154 parameters
3 restraints
All H-atom parameters refined
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2WA⋯O1Wⁱ	0.80 (4)	1.99 (4)	2.791 (2)	171 (6)
O1W—H1W⋯O1	0.81 (2)	1.98 (2)	2.785 (2)	177 (3)
O1W—H2WB⋯O1Wⁱⁱ	0.80 (6)	2.04 (5)	2.795 (2)	156 (6)
N3—H1N3⋯N1ⁱⁱⁱ	0.89 (2)	2.14 (2)	3.017 (2)	169 (2)
C1—H1⋯N2^iv	0.98 (2)	2.61 (2)	3.206 (2)	119 (1)
C2—H2⋯O1W^iv	0.95 (2)	2.58 (2)	3.508 (2)	164 (1)
C3—H3⋯Cg1^v	0.97 (2)	2.98 (2)	3.914 (2)	164 (2)
C3—H3⋯Cg1ⁱⁱⁱ	0.97 (2)	2.98 (2)	3.914 (2)	164 (2)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y+1, -z; (iv) -x+2, -y+2, -z; (v) x+1, y, z-1.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807065683/ci2534sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065683/ci2534Isup2.hkl

checkCIF report

Comment top

Substituted 2-aminopyrimidines are very important compounds in molecular recognition and supramolecular chemistry (Desiraju, 1989; Lehn, 1995) for the presence of nice donor-acceptor arrays (Aakeroy et al., 2006; Etter, 1990; Fun et al., 2006; Gallagher, et al., 2004; Goswami & Mahapatra, 1999). The donor-acceptor arrangement of the title molecule differs from the 2-aminopyrimidine based compounds (Goswami, Jana, Das et al., 2007; Goswami, Jana, Hazra et al., 2007). These types of compounds are also important for the metal coordination and related studies (Smith et al., 1998; Wang et al., 2006). The coordination chemistry of the title compound is under investigations.

Molecules of the title compound lie across a crystallographic inversion centre (Fig. 1). All bond lengths and angles have normal values (Allen et al., 1987). The N,N-di-pyrimidin-2-yl-terepthalamide molecule has a staggered conformation. The orientation of the pyrimidine ring (C1–C4/N1/N2) with respect to the benzene ring (C6–C8/C6A–C8A) can be described by the dihedral angle formed by these planes of 80.78 (6)° and the torsion angle C4–N3–C5–C6 of -169.50 (11)°. The two pyrimidine rings are parallel by virtue of the centre of symmetry. The pyrimidine and benzene rings form dihedral angles of 41.41 (7)° and 40.26 (7)°, respectively, with the amide plane.

The structure shows O—H···O and C—H···O hydrogen bond between water and N,N-di-pyrimidin-2-yl-terepthalamide molecule. In the crystal packing (Fig. 2), the molecules are linked by N—H···N and C—H···N hydrogen bonds into a two-dimensional network parallel to the (1 1 1) plane. The O—H···O and C—H···O hydrogen bonds (Table 1) involving the water molecules link the adjacent layers into a three-dimensional network. The crystal structure is further stablilized by C—H···π interactions involving the benzene ring (centroid Cg1).

Related literature top

For bond-length data, see: Allen et al. (1987). For related literature on supramolecular chemistry, see: Desiraju (1989); Lehn (1995). For related structures, see: Goswami, Jana, Das et al. (2007); Goswami, Jana, Hazra et al. (2007). For related literaure on coordination chemistry and applications of aminopyrimidine derivatives, see: Aakeroy et al. (2006); Etter (1990); Fun et al. (2006); Gallagher et al. (2004); Goswami & Mahapatra (1999); Smith et al. (1998); Wang et al. (2006).

Experimental top

A solution of terepthaloyl chloride (203 mg, 1 mmol), in dry CH₂Cl₂ (20 ml) was put in a round bottle flask under nitrogen atmosphere. 2-Aminopyrimidine (190 mg, 2 mmol) containing triethylamine (0.55 ml) in dry CH₂Cl₂ (15 ml) was added dropwise. The reaction mixture was stirred at room temperature for 10 h. The reaction mixture was dried, washed with sodium bicarbonate solution, and then extracted with CH₂Cl₂ (4 × 20 ml). The crude mixture was purified by column chromatography (silica gel, 100–200 mesh) using 20% ethyl acetate-petroleum ether solution as eluent to afford a white solid compound (188 mg, 65%). Single crystals of the title compound were grown by slow evaporation of a CHCl₃—CH₃OH (3:1 v/v) solution (m.p. 457–459 K).

Structure description top

For bond-length data, see: Allen et al. (1987). For related literature on supramolecular chemistry, see: Desiraju (1989); Lehn (1995). For related structures, see: Goswami, Jana, Das et al. (2007); Goswami, Jana, Hazra et al. (2007). For related literaure on coordination chemistry and applications of aminopyrimidine derivatives, see: Aakeroy et al. (2006); Etter (1990); Fun et al. (2006); Gallagher et al. (2004); Goswami & Mahapatra (1999); Smith et al. (1998); Wang et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 60% probability displacement ellipsoids and the atomic numbering. One of the H atoms of the water molecule is disordered over two positions. The dashed line indicates a hydrogen bond. Atoms labelled with the suffix A are generated by the symmetry operation (-x, 1 - y, 1 - z).
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

N,N'-Bis(pyrimidin-2-yl)terephthalamide dihydrate top

Crystal data top

C₁₆H₁₂N₆O₂·2H₂O	Z = 1
M_r = 356.35	F(000) = 186
Triclinic, P1	D_x = 1.567 Mg m⁻³
Hall symbol: -P 1	Melting point = 457–459 K
a = 5.0733 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3233 (1) Å	Cell parameters from 2202 reflections
c = 9.9622 (2) Å	θ = 2.3–30.0°
α = 68.220 (1)°	µ = 0.12 mm⁻¹
β = 75.441 (1)°	T = 100 K
γ = 82.333 (1)°	Block, colourless
V = 377.72 (1) Å³	0.33 × 0.22 × 0.08 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2202 independent reflections
Radiation source: fine-focus sealed tube	1982 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 2.3°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.963, T_max = 0.991	l = −13→14
12751 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	All H-atom parameters refined
S = 1.12	w = 1/[σ²(F_o²) + (0.0387P)² + 0.2638P] where P = (F_o² + 2F_c²)/3
2202 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.39 e Å⁻³
3 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₆H₁₂N₆O₂·2H₂O	γ = 82.333 (1)°
M_r = 356.35	V = 377.72 (1) Å³
Triclinic, P1	Z = 1
a = 5.0733 (1) Å	Mo Kα radiation
b = 8.3233 (1) Å	µ = 0.12 mm⁻¹
c = 9.9622 (2) Å	T = 100 K
α = 68.220 (1)°	0.33 × 0.22 × 0.08 mm
β = 75.441 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2202 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1982 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.991	R_int = 0.035
12751 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.106	All H-atom parameters refined
S = 1.12	Δρ_max = 0.39 e Å⁻³
2202 reflections	Δρ_min = −0.26 e Å⁻³
154 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	Occ. (<1)
O1	0.40513 (19)	0.85138 (12)	0.21674 (10)	0.0152 (2)
N1	0.7704 (2)	0.64103 (14)	−0.09155 (12)	0.0131 (2)
N2	0.9113 (2)	0.77862 (14)	0.05021 (12)	0.0134 (2)
N3	0.5215 (2)	0.61544 (14)	0.14450 (12)	0.0124 (2)
H1N3	0.441 (4)	0.530 (2)	0.1395 (19)	0.013 (4)*
C1	1.1248 (3)	0.83918 (16)	−0.06205 (14)	0.0135 (2)
H1	1.248 (4)	0.908 (2)	−0.0464 (19)	0.016 (4)*
C2	1.1741 (3)	0.80284 (17)	−0.19128 (14)	0.0144 (2)
H2	1.328 (4)	0.846 (2)	−0.270 (2)	0.018 (4)*
C3	0.9898 (3)	0.70138 (17)	−0.20052 (14)	0.0144 (2)
H3	1.021 (4)	0.669 (2)	−0.287 (2)	0.015 (4)*
C4	0.7440 (2)	0.68481 (15)	0.02820 (13)	0.0113 (2)
C5	0.3775 (2)	0.69938 (16)	0.23761 (13)	0.0121 (2)
C6	0.1803 (2)	0.59197 (16)	0.37078 (13)	0.0114 (2)
C7	−0.0689 (3)	0.67033 (16)	0.41794 (14)	0.0131 (2)
H7	−0.118 (4)	0.789 (2)	0.3599 (19)	0.015 (4)*
C8	0.2492 (2)	0.42173 (16)	0.45293 (14)	0.0126 (2)
H8	0.419 (4)	0.368 (2)	0.4211 (19)	0.014 (4)*
O1W	0.2790 (3)	0.96683 (17)	0.45548 (13)	0.0296 (3)
H1W	0.309 (5)	0.934 (3)	0.386 (2)	0.034 (6)*
H2WA	0.123 (6)	0.994 (7)	0.484 (6)	0.050 (15)*	0.50
H2WB	0.380 (10)	1.013 (7)	0.479 (7)	0.064 (18)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0159 (4)	0.0143 (4)	0.0149 (4)	−0.0037 (3)	0.0011 (3)	−0.0063 (3)
N1	0.0123 (5)	0.0147 (5)	0.0122 (5)	−0.0017 (4)	−0.0013 (4)	−0.0054 (4)
N2	0.0125 (5)	0.0142 (5)	0.0132 (5)	−0.0022 (4)	−0.0009 (4)	−0.0053 (4)
N3	0.0117 (5)	0.0136 (5)	0.0116 (5)	−0.0040 (4)	0.0014 (4)	−0.0057 (4)
C1	0.0118 (5)	0.0128 (5)	0.0151 (6)	−0.0018 (4)	−0.0026 (4)	−0.0040 (4)
C2	0.0110 (5)	0.0168 (6)	0.0128 (5)	−0.0028 (4)	0.0002 (4)	−0.0035 (4)
C3	0.0134 (5)	0.0179 (6)	0.0116 (5)	−0.0016 (4)	−0.0009 (4)	−0.0057 (5)
C4	0.0104 (5)	0.0112 (5)	0.0111 (5)	−0.0006 (4)	−0.0008 (4)	−0.0033 (4)
C5	0.0108 (5)	0.0148 (5)	0.0105 (5)	−0.0018 (4)	−0.0013 (4)	−0.0047 (4)
C6	0.0106 (5)	0.0145 (5)	0.0098 (5)	−0.0035 (4)	−0.0006 (4)	−0.0052 (4)
C7	0.0127 (5)	0.0140 (5)	0.0123 (5)	−0.0012 (4)	−0.0014 (4)	−0.0049 (4)
C8	0.0104 (5)	0.0154 (5)	0.0124 (5)	−0.0014 (4)	−0.0006 (4)	−0.0064 (4)
O1W	0.0388 (7)	0.0353 (7)	0.0186 (5)	−0.0039 (5)	−0.0004 (5)	−0.0170 (5)

Geometric parameters (Å, º) top

O1—C5	1.2252 (15)	C3—H3	0.970 (18)
N1—C4	1.3429 (15)	C5—C6	1.5006 (16)
N1—C3	1.3441 (16)	C6—C8	1.3967 (17)
N2—C4	1.3325 (16)	C6—C7	1.3976 (17)
N2—C1	1.3403 (16)	C7—C8ⁱ	1.3937 (17)
N3—C5	1.3734 (15)	C7—H7	0.980 (18)
N3—C4	1.4037 (15)	C8—C7ⁱ	1.3937 (17)
N3—H1N3	0.886 (18)	C8—H8	0.951 (18)
C1—C2	1.3850 (17)	O1W—H1W	0.807 (19)
C1—H1	0.976 (18)	O1W—H2WA	0.80 (2)
C2—C3	1.3810 (17)	O1W—H2WB	0.80 (2)
C2—H2	0.956 (18)

C4—N1—C3	115.24 (10)	N1—C4—N3	115.16 (10)
C4—N2—C1	115.74 (11)	O1—C5—N3	123.59 (11)
C5—N3—C4	123.80 (10)	O1—C5—C6	120.82 (11)
C5—N3—H1N3	117.2 (11)	N3—C5—C6	115.59 (10)
C4—N3—H1N3	116.3 (11)	C8—C6—C7	120.14 (11)
N2—C1—C2	122.42 (11)	C8—C6—C5	121.39 (11)
N2—C1—H1	116.0 (10)	C7—C6—C5	118.30 (11)
C2—C1—H1	121.5 (10)	C8ⁱ—C7—C6	119.91 (11)
C3—C2—C1	116.73 (11)	C8ⁱ—C7—H7	119.9 (10)
C3—C2—H2	121.6 (11)	C6—C7—H7	120.2 (10)
C1—C2—H2	121.7 (11)	C7ⁱ—C8—C6	119.95 (11)
N1—C3—C2	122.62 (11)	C7ⁱ—C8—H8	119.9 (11)
N1—C3—H3	118.1 (11)	C6—C8—H8	120.2 (11)
C2—C3—H3	119.3 (11)	H1W—O1W—H2WA	116 (4)
N2—C4—N1	127.22 (11)	H1W—O1W—H2WB	128 (5)
N2—C4—N3	117.53 (11)	H2WA—O1W—H2WB	111 (6)

C4—N2—C1—C2	−1.83 (18)	C4—N3—C5—O1	10.1 (2)
N2—C1—C2—C3	0.61 (19)	C4—N3—C5—C6	−169.50 (11)
C4—N1—C3—C2	−0.68 (19)	O1—C5—C6—C8	−137.21 (13)
C1—C2—C3—N1	0.72 (19)	N3—C5—C6—C8	42.36 (16)
C1—N2—C4—N1	1.96 (19)	O1—C5—C6—C7	38.15 (17)
C1—N2—C4—N3	178.50 (11)	N3—C5—C6—C7	−142.27 (12)
C3—N1—C4—N2	−0.73 (19)	C8—C6—C7—C8ⁱ	−0.1 (2)
C3—N1—C4—N3	−177.34 (11)	C5—C6—C7—C8ⁱ	−175.54 (11)
C5—N3—C4—N2	36.36 (18)	C7—C6—C8—C7ⁱ	0.1 (2)
C5—N3—C4—N1	−146.68 (12)	C5—C6—C8—C7ⁱ	175.39 (11)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2WA···O1Wⁱⁱ	0.80 (4)	1.99 (4)	2.791 (2)	171 (6)
O1W—H1W···O1	0.81 (2)	1.98 (2)	2.785 (2)	177 (3)
O1W—H2WB···O1Wⁱⁱⁱ	0.80 (6)	2.04 (5)	2.795 (2)	156 (6)
N3—H1N3···N1^iv	0.89 (2)	2.14 (2)	3.017 (2)	169 (2)
C1—H1···N2^v	0.98 (2)	2.61 (2)	3.206 (2)	119 (1)
C2—H2···O1W^v	0.95 (2)	2.58 (2)	3.508 (2)	164 (1)
C3—H3···Cg1^vi	0.97 (2)	2.98 (2)	3.914 (2)	164 (2)
C3—H3···Cg1^iv	0.97 (2)	2.98 (2)	3.914 (2)	164 (2)

Symmetry codes: (ii) −x, −y+2, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+1, −y+1, −z; (v) −x+2, −y+2, −z; (vi) x+1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₆O₂·2H₂O
M_r	356.35
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.0733 (1), 8.3233 (1), 9.9622 (2)
α, β, γ (°)	68.220 (1), 75.441 (1), 82.333 (1)
V (Å³)	377.72 (1)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.33 × 0.22 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	12751, 2202, 1982
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.106, 1.12
No. of reflections	2202
No. of parameters	154
No. of restraints	3
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2WA···O1Wⁱ	0.80 (4)	1.99 (4)	2.791 (2)	171 (6)
O1W—H1W···O1	0.81 (2)	1.98 (2)	2.785 (2)	177 (3)
O1W—H2WB···O1Wⁱⁱ	0.80 (6)	2.04 (5)	2.795 (2)	156 (6)
N3—H1N3···N1ⁱⁱⁱ	0.89 (2)	2.14 (2)	3.017 (2)	169 (2)
C1—H1···N2^iv	0.98 (2)	2.61 (2)	3.206 (2)	119 (1)
C2—H2···O1W^iv	0.95 (2)	2.58 (2)	3.508 (2)	164 (1)
C3—H3···Cg1^v	0.97 (2)	2.98 (2)	3.914 (2)	164 (2)
C3—H3···Cg1ⁱⁱⁱ	0.97 (2)	2.98 (2)	3.914 (2)	164 (2)

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

Footnotes

¹This paper is dedicated to His Majesty, Thai King Bhumibol Adulyadej on the occasion of his 80th Birthday Anniversary which fell on December 5th, 2007.

‡Additional correspondence author, email: suchada.c@psu.ac.th.

Acknowledgements

SJ, AH and SG acknowledge the DST (grant No. SR/S1/OC-13/2005) and CSIR [grant No. 01(1913)/04/EMR-II], Government of India, for financial support. SJ and AH thank the CSIR, Government of India, for research fellowships. SC thanks the Prince of Songkla University, Thailand, for support. The authors also thank the Malaysian Government and Universiti Sains Malaysia for a Scientific Advancement Grant Allocation (SAGA, grant No. 304/PFIZIK/653003/A118).

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