1,2-Ethyl­enediaminium bis­(2-benzamido­benzoate)

Mavlonbek Ziyaev; Jamshid Ashurov; Samat Talipov; Bakhtiyar Ibragimov

doi:10.1107/S1600536813021028

. 2013 Aug 7;69(Pt 9):o1388. doi: 10.1107/S1600536813021028

1,2-Ethylenediaminium bis(2-benzamidobenzoate)

Mavlonbek Ziyaev ^a,^*, Jamshid Ashurov ^a, Samat Talipov ^a, Bakhtiyar Ibragimov ^a

PMCID: PMC3884477 PMID: 24427030

Abstract

In the title salt, C₂H₁₀N₂ ²⁺·2C₁₄H₁₀NO₃ ⁻, the ethylenediaminium dication lies on an inversion centre. In the anion, the benzene rings make a dihedral angle of 33.87 (9)° and intramolecular N—H⋯O and C—H⋯O hydrogen bonds occur. All the amino H atoms are involved in N—H⋯O hydrogen bonds. These hydrogen bonds link the ionic units into a three-dimensional network. In addition, the crystal structure also features weak C—H⋯O interactions.

Related literature

For the crystal structure of 1,2-ethylenediammonium salts of aromatic acids, see: Shen-Tu et al. (2008 ▶); Zhao & Feng (2011 ▶). For the crystal structure of the 2-benzamidobenzoyl acid Cu^II coordination compound, see: Kaizer et al. (2006 ▶). graphic file with name e-69-o1388-scheme1.jpg

Experimental

Crystal data

0.5C₂H₁₀N₂ ²⁺·C₁₄H₁₀NO₃ ⁻
M _r = 271.29
Monoclinic,
a = 5.314 (1) Å
b = 13.745 (2) Å
c = 18.580 (4) Å
β = 93.66 (2)°
V = 1354.3 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.77 mm⁻¹
T = 293 K
0.6 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.699, T _max = 1.000
5702 measured reflections
2772 independent reflections
1851 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.117
S = 0.95
2772 reflections
197 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, GLOBAL. DOI: 10.1107/S1600536813021028/zq2204sup1.cif

e-69-o1388-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021028/zq2204Isup2.hkl

e-69-o1388-Isup2.hkl^{(136.1KB, hkl)}

Click here for additional data file.^{(10.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813021028/zq2204Isup3.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
N1—H1⋯O2	0.90 (2)	1.81 (2)	2.608 (2)	146.8 (19)
N1s—H1A⋯O1	0.94 (2)	1.89 (2)	2.807 (2)	165 (2)
N1s—H1B⋯O3ⁱ	0.98 (2)	1.76 (2)	2.729 (2)	170 (2)
N1s—H1C⋯O2ⁱⁱ	0.94 (2)	1.84 (2)	2.753 (2)	163 (2)
C2s—H2B⋯O3ⁱⁱⁱ	0.97	2.59	3.315 (2)	131
C6—H6⋯O3ⁱⁱⁱ	0.93	2.50	3.319 (2)	147
C9—H9⋯O1	0.93	2.25	2.863 (2)	123

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

Acknowledgments

This work was supported by a Grant for Fundamental Research from the Center of Science and Technology, Uzbekistan (No. FA–F3–T-141).

supplementary crystallographic information

1. Comment

The asymmetric unit is composed of one 2-benzamidobenzoate anion and one-half of the ethylenediaminium cation (Fig. 1). In the 2-benzamidobenzoate anion the carboxylate group is slightly rotated with respect to the benzene ring, the dihedral angle between the mean planes is 6.1 (1)°, while the peptide bond exhibits an angle of 6.1 (8)° relative to the benzene ring. The angle between the peptide bond and the second benzene ring is 29.6 (7)°. An intramolecular N—H···O hydrogen bond is observed between the amino group and one O atom of the carboxylate (Table 1). Both amine N atoms of the ethylenediamine are protonated and all nitrogen H atoms are involved in N—H···O hydrogen bonds (Table 1, Fig. 2). In the crystal structure, anions are bridged by diammonium N–H(b) and N–H(c) bonds via the carboxylate O atoms forming centrosymmetrical H-bonded strands along the a axis. Other intermolecular N—H···O hydrogen bonds between the diammonium N–H(a) bonds and the carbonyl O atoms link these strands into sheets parallel to (011) and (0–11) planes forming a three-dimensional network. In addition, C—H···O weak interactions further stabilize the crystal structure. Some related crystal structures of interest were previously reported by Shen-Tu et al. (2008), Zhao and Feng (2011) and Kaizer et al. (2006).

2. Experimental

A 1:2 mixture of 1,2-ethylenediamine and 2-benzamidobenzoic acid were dissolved in ethanol. Colourless prismatic crystals suitable for a X-ray analysis were obtained after 5 days.