3-Amino­benzoic acid–4-nitro­benzoic acid (1/1)

Ching Kheng Quah; Samuel Robinson Jebas; Hoong-Kun Fun

doi:10.1107/S1600536808037112

. 2008 Nov 13;64(Pt 12):o2333. doi: 10.1107/S1600536808037112

3-Aminobenzoic acid–4-nitrobenzoic acid (1/1)

Ching Kheng Quah ^a, Samuel Robinson Jebas ^a,^‡, Hoong-Kun Fun ^a,^*

PMCID: PMC2960102 PMID: 21581308

Abstract

In the title 1:1 adduct, C₇H₅NO₄·C₇H₇NO₂, the nitro group of the 4-nitro benzoic acid is twisted from the attached ring by 4.40 (8)°. In the crystal, the molecules are linked into ribbon-like structures along [150] and [1 Inline graphic 0] via O—H⋯O, N—H⋯O, N—H⋯N and C—H⋯O intermolecular hydrogen bonds.

Related literature

For the applications of 3-aminobenzoic acid, see; Windholz (1976 ▶). For related structures, see: Bowers et al. (2005 ▶); Tonogaki et al. (1993 ▶); Voogd et al. (1980 ▶).

Experimental

Crystal data

C₇H₅NO₄·C₇H₇NO₂
M _r = 304.26
Monoclinic,
a = 25.3707 (8) Å
b = 4.9875 (2) Å
c = 21.7276 (7) Å
β = 109.230 (2)°
V = 2595.93 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100.0 (1) K
0.24 × 0.09 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.971, T _max = 0.993
15472 measured reflections
3759 independent reflections
2197 reflections with I > 2σ(I)
R _int = 0.068

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.179
S = 1.01
3759 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037112/ci2714sup1.cif

e-64-o2333-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037112/ci2714Isup2.hkl

e-64-o2333-Isup2.hkl^{(180.6KB, hkl)}

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
O4—H1O4⋯O5ⁱ	0.89 (4)	1.73 (4)	2.612 (2)	171 (3)
O6—H1O6⋯O3ⁱⁱ	0.91 (4)	1.75 (4)	2.652 (2)	171 (4)
N2—H1N1⋯O2ⁱⁱⁱ	1.06 (4)	2.29 (4)	3.309 (3)	161 (3)
N2—H2N2⋯O2^iv	0.90 (3)	2.60 (3)	3.351 (3)	142 (2)
C2—H2A⋯O5^v	0.95	2.58	3.288 (3)	131
C4—H4A⋯O6^iv	0.95	2.55	3.339 (3)	141
C10—H10A⋯O1ⁱⁱⁱ	0.95	2.57	3.460 (3)	156

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

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. CKQ thanks Universiti Sains Malaysia for a student assistanceship.

supplementary crystallographic information

Comment

3-Aminobenzoic acid is used as an intermediate for dyes, pesticides and in other organic synthesis (Windholz, 1976). The crystal structures of 3-aminobenzoic acid (Voogd et al., 1980) and 4-aminobenzoic acid-4-nitrobenzoic acid have been reported (Bowers et al., 2005). As a part of our investigation of the interactions between acids, we report herein the crystal structure of the title compound.

The asymmetric unit (Fig. 1) contains one 3-aminobenzoic acid molecule and one 4-nitrobenzoic acid molecule. The bond lengths and angles of 3-aminobenzoic acid and 4-nitrobenzoic acid are found to have normal values (Voogd et al., 1980; Tonogaki et al., 1993). Both the molecules are almost planar with the maximum deviation from planarity being 0.026 (2) Å for atom O5 of 3-aminobenzoic acid molecule, and 0.078 (2) Å for atom O1 of nitrobenzoic acid molecule. In the 4-nitrobenzoic acid molecule, the nitro group is twisted slightly from the attached ring; the dihedral angle between C1—C6 and O1—O2/C3/N1 planes is 4.40 (8)°.

The crystal packing is consolidated by O—H···O, N—H···O, N—H···N and C—H···O intermolecular hydrogen bonds (Table 1). These hydrogen bonds link the molecules into ribbon like structures along [1 5 0] and [1 5 0] (Fig.2).

Experimental

3-Aminobenzoic acid and 4-nitrobenzoic acid were mixed in methanol (20 ml) in a 1:1 molar ratio. The clear colourless solution obtained was allowed to evaporate slowly. Colourless crystals were obtained after 2 d.