Benzene-1,3,5-tricarb­oxy­lic acid–5-(4-pyrid­yl)pyrimidine (1/1)

Yan-Ke Jiang; Gui-Ge Hou

doi:10.1107/S1600536811051075

. 2011 Dec 3;68(Pt 1):o6. doi: 10.1107/S1600536811051075

Benzene-1,3,5-tricarboxylic acid–5-(4-pyridyl)pyrimidine (1/1)

Yan-Ke Jiang ^a, Gui-Ge Hou ^b,^*

PMCID: PMC3254286 PMID: 22259560

Abstract

In the pyrimidine molecule of the title compound, C₉H₇N₃·C₉H₆O₆, the pyridine ring is oriented at 33.26 (11)° with respect to the pyrimidine ring. In the benzene-1,3,5-tricarboxylic acid molecule, the three carboxy groups are twisted by 7.92 (9), 8.68 (10) and 17.07 (10)° relative to the benzene ring. Classical O—H⋯N and O—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯N hydrogen bonds occur in the crystal structure.

Related literature

For hydrogen bonding in pyrimidine derivatives, see: Hou et al. (2011 ▶); Horikoshi et al. (2004 ▶); Georgiev et al. (2004 ▶); Santoni et al. (2008 ▶); Huang & Parquette (2000 ▶). For co-crystals of organic acids and pyrimidine, see: Bhogala & Nangia(2003 ▶); Du et al. (2005 ▶); Hou et al. (2008 ▶).

Experimental

Crystal data

C₉H₇N₃·C₉H₆O₆
M _r = 367.31
Monoclinic,
a = 8.3532 (19) Å
b = 14.865 (3) Å
c = 13.066 (3) Å
β = 98.325 (4)°
V = 1605.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.32 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
8278 measured reflections
2967 independent reflections
2142 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.130
S = 1.04
2967 reflections
256 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051075/xu5398sup1.cif

e-68-000o6-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051075/xu5398Isup2.hkl

e-68-000o6-Isup2.hkl^{(145.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811051075/xu5398Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3ⁱ	0.95 (3)	1.70 (3)	2.652 (2)	173 (3)
O3—H3A⋯O2ⁱⁱ	0.92 (3)	1.84 (3)	2.720 (2)	161 (3)
O5—H5A⋯N1	0.95 (3)	1.68 (3)	2.626 (2)	177 (3)
C3—H3⋯O3ⁱⁱ	0.93	2.48	3.367 (3)	159
C14—H14⋯N2ⁱⁱⁱ	0.93	2.59	3.335 (3)	137

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank the Scientific Research Project of Chongqing Education Committee, China (KJ100720 and KJTD201020) and Chongqing Technology and Business University, China (2010-56-07) for supporting this work.

supplementary crystallographic information

Comment

Some pyrimidine derivatives, such as such as 5, 5'-dipyrimidine, 1,2-bis(5'-pyrimidyl)ethyne, 5-(3-pyridyl)pyrimidine (L), 5-phenyl-2-(4-pyrid-yl)pyrimidine, and 4-(pyridin-2-yl)pyrimidine-2-sulfonate, could form strong hydrogen-bond interaction and play an essential role in synthesis of supra-molecular structure (Hou et al., 2011; Horikoshi et al., 2004; Georgiev et al., 2004; Santoni et al., 2008; Huang et al., 2000). The co-crystal sates of acid···pyridine and acid···pyrimidine systems have been reported (Bhogala et al., 2003; Du et al., 2005; Hou et al., 2008). Here we report the co-crystal states of L1 and L2.

The title molecular structure is shown in Fig. 1. The asymmetric unit contains 5-(4-pyridyl)pyrimidine molecule (L1) and a benzene-1,3,5-tricarboxylic acid molecule (L2). In the crystal, L1 and L2 arrange in an alternate disposition along the crystallographic c-axis. A H-bonding driven double chain was generated from O—H···N and O—H···O hydrogen bonds between these molecules (Fig. 2). The asymmetric hydrogen bonds influence the intramolecular coplanar of L2 and different dihedral angles of 7.92 (9), 8.68 (10) and 17.07 (10)° are formed between benzene ring and the carboxyl groups. Pyridine ring is twisted to pyrimidine ring at a dihedral angle of 33.26 (11)°, but nearly coplanar with benzene ring of L2 (the dihedral angle, 12.0 (8)°).

Experimental

A CH₂Cl₂ and CH₃CN solution (15 mL, 1:1, v/v) of 5-(4-pyridyl)pyrimidine molecule and benzene-1,3,5-tricarboxylic acid (21.0 mg, 0.1 mmol) was kept at room temperature. Upon slow evaporation of the solvent about 5 days, colorless crystals were obtained.