2,2′-Diamino-N,N′-(o-phenyl­ene)di­benz­amide

Irvin Booysen; Thomas I A Gerber; Eric Hosten; Peter Mayer

doi:10.1107/S1600536809009283

. 2009 Mar 25;65(Pt 4):o850. doi: 10.1107/S1600536809009283

2,2′-Diamino-N,N′-(o-phenylene)dibenzamide

Irvin Booysen ^a, Thomas I A Gerber ^a,^*, Eric Hosten ^a, Peter Mayer ^b

PMCID: PMC2968993 PMID: 21582568

Abstract

In the structure of the title compound, C₂₀H₁₈N₄O₂, the N—H and C=O bonds are trans to each other and the amide O atoms are syn to the ortho amino N atom in the benzoyl rings. The amide groups form dihedral angles of 8.4 (2) and 13.8 (2)° with their respective benzoyl rings, and dihedral angles of 51.85 (16) and 51.19 (17)° with the phenylenediamine ring. In the crystal, a centrosymmetric dimer is formed by intermolecular N—H⋯O hydrogen bonds, resulting in an R ₂ ²(14) descriptor on a unitary level of graph-set analysis, and three intramolecular N—H⋯O bonds also occur.

Related literature

For the synthesis, see: Black & Rothnie (1983 ▶). For metal coordination, see: Booysen et al. (2008 ▶). For stereoselectivity in synthesis, see: Valik et al. (2002 ▶). For applications of polyamides, see: Kang et al. (2001 ▶). For related structures, see Gowda et al. (2003 ▶, 2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₀H₁₈N₄O₂
M _r = 346.38
Monoclinic,
a = 8.7464 (3) Å
b = 14.4308 (6) Å
c = 13.6161 (6) Å
β = 97.291 (3)°
V = 1704.69 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.16 × 0.14 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
7575 measured reflections
3893 independent reflections
2085 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.122
S = 0.99
3893 reflections
308 parameters
All H-atom parameters refined
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009283/sj2594sup1.cif

e-65-0o850-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009283/sj2594Isup2.hkl

e-65-0o850-Isup2.hkl^{(190.9KB, 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
N1—H1⋯O2	0.849 (17)	1.986 (18)	2.694 (2)	140.4 (17)
N3—H3⋯O1ⁱ	0.86 (2)	2.10 (2)	2.929 (2)	163.0 (17)
N4—H42⋯O2	0.97 (3)	1.88 (3)	2.646 (3)	134 (2)
N2—H21⋯O1	0.95 (2)	1.95 (2)	2.667 (2)	130.2 (19)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Professor P. Klüfers for generous allocation of diffractometer time.

supplementary crystallographic information

Comment

In the present work the structure of N,N'-(1,2-phenylene)bis(2-aminobenzamide) has been determined to explore its suitability as a tetradentate ligand for various metal ions. The conformations of N—H and C═O bonds in the amide groups are trans to each other (Fig. 1), similar to that observed in other benzamides and benzanilides (Gowda et al., 2003, 2008). Also, the conformations of the amide O atoms are syn to the ortho amino groups in the benzoyl rings. The amide group N1HC1O1 makes dihedral angles of 8.4 (2)° and 51.85 (16)° with the benzoyl and phenylene rings respectively. For the N3HC14O2 group, these values are 13.8 (2)° and 51.19 (17)°. The C2–C7 and C15–C20 benzoyl rings form dihedral angles of 59.64 (17)° and 64.86 (18)° respectively with the phenylene ring.

The conformational arrangement of the rings is mainly determined by intra- and intermolecular hydrogen-bonds. The graph set descriptor for the intramolecular hydrogen bonds is S(6)S(6)S(7) on a unitary level. Centrosymmetric dimers are formed by two intermolecular hydrogen bonds of the type N—H···O resulting in a R²₂(14) descriptor on a unitary level. The hydrogen bonding pattern is shown in Fig. 2.

Experimental

The title compound was prepared according to the literature method (Black & Rothnie, 1983). The purity of the compound was checked by determining its melting point. It was characterized by recording its IR and ¹H NMR spectra. Single crystals of the title compound were obtained from a pyridine/ethanol (1:1, v/v) solution.