2,4,6-Trimethyl­pyridinium 4-nitro­benzoate–4-nitro­benzoic acid (1/1)

Muhammad Athar Abbasi; Kenneth Nazir; Mehmet Akkurt; Aziz-ur-Rehman; Islam Ullah Khan; Ghulam Mustafa

doi:10.1107/S1600536811032922

. 2011 Aug 27;67(Pt 9):o2375. doi: 10.1107/S1600536811032922

2,4,6-Trimethylpyridinium 4-nitrobenzoate–4-nitrobenzoic acid (1/1)

Muhammad Athar Abbasi ^a,^‡, Kenneth Nazir ^a, Mehmet Akkurt ^b,^*, Aziz-ur-Rehman ^a, Islam Ullah Khan ^a, Ghulam Mustafa ^a

PMCID: PMC3200921 PMID: 22058980

Abstract

The asymmetric unit of the title co-crystal, C₈H₁₂N⁺·C₇H₄NO₄ ⁻·C₇H₅NO₄, contains two cations, two anions and two neutral 4-nitrobenzoic acid molecules. In the crystal, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds connect the ions and molecules, forming a three-dimensional network.

Related literature

For related structures, see: Ishida et al. (2004 ▶); Quah et al. (2008 ▶); Dong et al. (2010 ▶). For bond-length data, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C₈H₁₂N⁺·C₇H₄NO₄ ⁻·C₇H₅NO₄
M _r = 455.42
Orthorhombic,
a = 14.4061 (15) Å
b = 8.4461 (10) Å
c = 36.787 (4) Å
V = 4476.1 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.54 × 0.44 × 0.37 mm

Data collection

Bruker APEXII CCD diffractometer
23612 measured reflections
5658 independent reflections
2131 reflections with I > 2σ(I)
R _int = 0.090

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.102
S = 0.79
5658 reflections
602 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032922/hb6339sup1.cif

e-67-o2375-sup1.cif^{(34.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032922/hb6339Isup2.hkl

e-67-o2375-Isup2.hkl^{(277KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811032922/hb6339Isup3.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
N1E—H1E⋯O3Dⁱ	0.86	1.78	2.636 (4)	171
N1F—H1F⋯O4Cⁱ	0.86	1.76	2.613 (4)	173
O4A—H1O⋯O4Dⁱⁱ	0.90	1.67	2.549 (5)	164
O4B—H2O⋯O3Cⁱⁱⁱ	0.90	1.65	2.536 (5)	165
C4E—H4E⋯O1B^iv	0.93	2.58	3.398 (7)	147
C7E—H7K⋯O4D^v	0.96	2.57	3.475 (6)	156
C7E—H7L⋯O1B^iv	0.96	2.55	3.455 (9)	158

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for providing financial support.

supplementary crystallographic information

Comment

The asymmetric unit of the title co-crystal, (I), contains two molecules of 2,4,6-trimethylpyridinium 4-nitrobenzoate and 4-nitrobenzoic acid (Fig. 1). All bond lengths and bond angles are as expected for this kind of compounds (Allen et al., 1987).

In the structure, the molecular packing is stabilized by intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds, forming a three dimensional network (Table 1, Figs. 2 & 3).

Experimental

10 ml of ethanol were taken in 25 ml round bottom flask and 1.25 g of p-nitrobenzoic acid were added and suspension was heated to homogenize the mixture. Then 1 ml of sym-collidine (2,4,6-trimethylpyridine) was added and this mixture was refluxed for 1.5 h. Then this solution was concentrated on water bath to half amount and poured into sample vial and left for crystallization. On crystallization, colourless prisms of (I) were obtained.