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

The organic mol-ecule of the title compound, C(16)H(12)N(6)O(2)·2H(2)O, 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 mol-ecules 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 mol-ecules link the adjacent layers into a three-dimensional network. In addition, a C-H⋯π inter-action 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 = 356.35

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.106

S = 1.12

2202 reflections

154 parameters

3 restraints

All H-atom parameters refined

Δρmax = 0.39 e Å−3

Δρmin = −0.26 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065683/ci2534Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H12N6O2·2H2O	Z = 1
Mr = 356.35	F000 = 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 = 2.3–30.0º
α = 68.220 (1)º	µ = 0.12 mm−1
β = 75.441 (1)º	T = 100.0 (1) K
γ = 82.333 (1)º	Block, colourless
V = 377.720 (12) 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)
Monochromator: graphite	Rint = 0.035
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.3º
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	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	All H-atom parameters refined
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0387P)2 + 0.2638P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
2202 reflections	Δρmax = 0.39 e Å−3
154 parameters	Δρmin = −0.26 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)

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)

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⋯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) ; (ii) ; (iii) ; (iv) ; (v) .