(1H-Pyrrol-2-ylmethylidene)(3-{[(1H-pyrrol-2-ylmethylidene)amino]methyl}benzyl)amine

Dong Wan Kim; Tae Ho Kim; Jineun Kim; Jae Sang Kim

doi:10.1107/S1600536810046799

. 2010 Nov 17;66(Pt 12):o3211. doi: 10.1107/S1600536810046799

(1H-Pyrrol-2-ylmethylidene)(3-{[(1H-pyrrol-2-ylmethylidene)amino]methyl}benzyl)amine

Dong Wan Kim ^a, Tae Ho Kim ^a,^*, Jineun Kim ^a, Jae Sang Kim ^a,^*

PMCID: PMC3011650 PMID: 21589504

Abstract

In the title compound, C₁₈H₁₈N₄, the dihedral angles between the pyrrole rings and the phenyl ring are 85.07 (8)° and 77.13 (9)°. Intermolecular N—H⋯N hydrogen bonds contribute to the stabilization of the crystal packing.

Related literature

For the synthesis of the title compound, see: Chakravorty & Holm (1964 ▶); Jasat & Dolphin, (1997 ▶). For related structures, see: Nativi et al. (2007 ▶).

Experimental

Crystal data

C₁₈H₁₈N₄
M _r = 290.36
Monoclinic,
a = 5.0010 (6) Å
b = 17.271 (2) Å
c = 17.764 (2) Å
β = 96.128 (9)°
V = 1525.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.15 × 0.05 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.988, T _max = 0.998
12454 measured reflections
2990 independent reflections
1550 reflections with I > 2σ(I)
R _int = 0.087

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.141
S = 0.98
2990 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046799/jh2230sup1.cif

e-66-o3211-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046799/jh2230Isup2.hkl

e-66-o3211-Isup2.hkl^{(146.8KB, 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⋯N3ⁱ	0.88	2.17	2.993 (3)	156
N4—H4⋯N2ⁱⁱ	0.88	2.12	2.949 (3)	158

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

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010–0016386).

supplementary crystallographic information

Comment

The design and synthesis of supramolcular ligands are based on the ability to organize the binding site and size complementarities in a proper way. Especially, metal ions assisted self-assembly are one of most powerful approaches to supramolecular architectures. For examples, the N4 type of tetradentate ligands, pyrrole-2-yl Schiff base and pyrrole-2-ylmethylene amines have been known for a long time (Chakravorty & Holm, 1964; Jasat & Dolphin, 1997).

In the asymmetric unit (Fig. 1), the dihedral angle between the pyrrole ring plane system and phenyl ring plane are 85.07 (8)° and 77.13 (9)°. All bond lengths and bond angles of pyrrole-2-ylmethylene group are are comparable to those observed in similar structures (Nativi et al., 2007).

In the crystal structure, intermolecular N—H···N hydrogen bonds are observed. These interactinos contribute to stabilization of the packing (Fig. 2).

Experimental

Pyrrole-2-carbaldehyde (1.9 g, 20 mmol) and 1,3-phenylenedimethanamine (1.36 g, 10 mmol) were dissolved in ethanol (20 ml). The mixture strirred for a while, and then a few drops of acetic acid was added. After about 30 min, a light yellow precipitate was observed. After about 20 min, the precipitate obtained from filtration was washed with ethanol, dried in vacuum. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.

FT—IR (KBr disk) 3166, 3110, 2830, 1641 cm^{-1. 1}H NMR (300 MHz, DMSO-d₆) 4.7 (s, 2H), 6.1 (d, 2H, J=4.2 Hz), 6.5 (t, 2H, J=2.8 Hz), 6.9 (d, 2H, J=4.2 Hz), 7.3 (m, 4H), 8.2 (s, 2H), 11.4 (broad s, 2H). ¹³C NMR (75 MHz, DMSO-d₆) 39.1, 64.3, 109.3, 114.2, 122.6, 126.9, 128.1, 130.4, 140.6, 152.9. EI—MS (m/z): 290 (M⁺).