organic compounds
N,N′-Bis(pyrimidin-2-yl)terephthalamide dihydrate1
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
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 (11) 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
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell 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
https://doi.org/10.1107/S1600536807065683/ci2534sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065683/ci2534Isup2.hkl
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
(silica gel, 100–200 mesh) using 20% ethyl acetate-petroleum ether solution as 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).All H atoms were located from the difference map and isotropically refined. One of the water hydrogen atoms is disordered over two positions with occupancies each 0.50. The O—H distances were restrained to be equal within 0.03 Å.
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
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 is further stablilized by C—H···π interactions involving the benzene ring (centroid Cg1).
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).
Data collection: APEX2 (Bruker, 2005); cell
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).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. |
C16H12N6O2·2H2O | Z = 1 |
Mr = 356.35 | F(000) = 186 |
Triclinic, P1 | Dx = 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 |
Bruker SMART APEXII CCD area-detector diffractometer | 2202 independent reflections |
Radiation source: fine-focus sealed tube | 1982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 2.3° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −11→11 |
Tmin = 0.963, Tmax = 0.991 | l = −13→14 |
12751 measured reflections |
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(Fo2) + (0.0387P)2 + 0.2638P] where P = (Fo2 + 2Fc2)/3 |
2202 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 0.39 e Å−3 |
3 restraints | Δρmin = −0.26 e Å−3 |
C16H12N6O2·2H2O | γ = 82.333 (1)° |
Mr = 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)° |
Bruker SMART APEXII CCD area-detector diffractometer | 2202 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1982 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.991 | Rint = 0.035 |
12751 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 3 restraints |
wR(F2) = 0.106 | All H-atom parameters refined |
S = 1.12 | Δρmax = 0.39 e Å−3 |
2202 reflections | Δρmin = −0.26 e Å−3 |
154 parameters |
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. |
x | y | z | Uiso*/Ueq | 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 |
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) |
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. |
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···N1iv | 0.89 (2) | 2.14 (2) | 3.017 (2) | 169 (2) |
C1—H1···N2v | 0.98 (2) | 2.61 (2) | 3.206 (2) | 119 (1) |
C2—H2···O1Wv | 0.95 (2) | 2.58 (2) | 3.508 (2) | 164 (1) |
C3—H3···Cg1vi | 0.97 (2) | 2.98 (2) | 3.914 (2) | 164 (2) |
C3—H3···Cg1iv | 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 |
Mr | 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) |
Tmin, Tmax | 0.963, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12751, 2202, 1982 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.39, −0.26 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
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···N2iv | 0.98 (2) | 2.61 (2) | 3.206 (2) | 119 (1) |
C2—H2···O1Wiv | 0.95 (2) | 2.58 (2) | 3.508 (2) | 164 (1) |
C3—H3···Cg1v | 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. |
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).
References
Aakeroy, C. B., Schultheiss, N., Desper, J. & Moore, C. (2006). New J. Chem. 30, 1452–1460. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12a) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. (1989). Crystal Engineering. The Design of Organic Solids. Amsterdam: Elsevier. Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Fun, H.-K., Goswami, S., Jana, S. & Chantrapromma, S. (2006). Acta Cryst. E62, o5332–o5334. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gallagher, J. F., Goswami, S., Chatterjee, B., Jana, S. & Dutta, K. (2004). Acta Cryst. C60, o229–o231. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Goswami, S., Jana, S., Das, N. K., Fun, H.-K. & Chantrapromma, S. (2007). J. Mol. Struct. doi:10.1016/j.molstruc.2007.07.005. In the press. Google Scholar
Goswami, S., Jana, S., Hazra, A., Fun, H.-K. & Chantrapromma, S. (2007). Supramol. Chem. 19. In the press. Google Scholar
Goswami, S. P. & Mahapatra, A. K. (1999). Supramol. Chem. 11, 25–33. Web of Science CSD CrossRef CAS Google Scholar
Lehn, J. M. (1995). Supramolecular Chemistry: Concepts and Perspectives. Weinheim: VCH. Google Scholar
Sheldrick, G. M. (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Smith, G., Cloutt, B. A., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1998). Inorg. Chem. 37, 3236–3242. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y.-H., Chu, K.-L., Chen, H.-C., Yeh, C.-W., Chan, Z.-K., Suen, M.-C., Chen, J.-D. & Wang, J.-C. (2006). CrystEngComm, 8, 84–93. CAS Google Scholar
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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).