2,17-Dichloro-8,9,10,11-tetra­hydro-19H-dibenzo[k,n][1,10,4,7]dioxadiaza­cyclo­penta­decine-7,12(6H,13H)-dione

Michaela Pojarová; Michal Dušek; Zdeňka Sedláková; Emanuel Makrlík

doi:10.1107/S1600536812020351

. 2012 May 12;68(Pt 6):o1698–o1699. doi: 10.1107/S1600536812020351

2,17-Dichloro-8,9,10,11-tetrahydro-19H-dibenzo[k,n][1,10,4,7]dioxadiazacyclopentadecine-7,12(6H,13H)-dione

Michaela Pojarová ^a,^*, Michal Dušek ^a, Zdeňka Sedláková ^b, Emanuel Makrlík ^c

PMCID: PMC3379293 PMID: 22719491

Abstract

In the crystal structure of the title compound, C₁₉H₁₈Cl₂N₂O₄, N—H⋯O hydrogen bonds link the molecules into infinite chains along the b axis. The structure also features weak C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π and (lone pair)⋯π interactions [Cl⋯centroid = 3.5871 (7) Å]. An intramolecular N—H⋯O bond occurs.

Related literature

For the synthesis, see: Ertul et al. (2009 ▶). For applications of macrocycles, see: Hayvali & Hayvali (2005 ▶); Kleinpeter et al. (1997 ▶); Jaiyu et al. (2007 ▶); Christensen et al. (1997 ▶); Alexander (1995 ▶).

Experimental

Crystal data

C₁₉H₁₈Cl₂N₂O₄
M _r = 409.25
Monoclinic,
a = 12.0877 (3) Å
b = 8.73462 (15) Å
c = 17.3712 (4) Å
β = 93.588 (2)°
V = 1830.48 (7) Å³
Z = 4
Cu Kα radiation
μ = 3.44 mm⁻¹
T = 120 K
0.31 × 0.22 × 0.21 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.175, T _max = 0.342
19596 measured reflections
3271 independent reflections
3210 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.074
S = 1.07
3271 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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: Mercury (Macrae et al., 2006 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020351/aa2058sup1.cif

e-68-o1698-sup1.cif^{(25.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020351/aa2058Isup2.hkl

e-68-o1698-Isup2.hkl^{(160.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.89	2.05	2.8945 (15)	158
C14—H14A⋯O3ⁱ	0.97	2.54	3.5026 (17)	172
C14—H14B⋯O3ⁱⁱ	0.97	2.34	3.2934 (17)	167
C16—H16B⋯O1ⁱⁱⁱ	0.97	2.59	3.2843 (17)	129
C19—H19A⋯Cl2^iv	0.97	2.81	3.6201 (14)	142
C9—H9⋯Cg1^v	0.93	2.88	3.8006 (14)	174
N1—H1N1⋯O1	0.90	2.16	2.5935 (15)	109

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

Acknowledgments

This study was supported financially by the project Praemium Academiae of the Academy of Science of the Czech Republic, the Grant Agency of the Faculty of Environmental Sciences, Czech University of Life Sciences, Prague (project No. 42900/1312/3114 ‘Environmental Aspects of Sustainable Development of Society’) and the Czech Ministry of Education, Youth and Sports (project ME09058).

supplementary crystallographic information

Comment

Polyazalactones together with polyoxalactones and polyethers are studied for their ability to act as multidentate ligands and to complex various cations. Polyazalactones can incorporate transition metals into their cavities via an ion-dipole interaction (Hayvali et al., 2005; Kleinpeter et al., 1997). They are studied for their role in bioprocesses, catalysis, material science, and transport and separation (Jaiyu et al., 2007; Christensen et al., 1997; Alexander, 1995). In this paper, we report a crystal structure of lactam ionophore (Fig. 1 and Scheme). The macrocycle consists of two phenyl rings substituted with chlorine atom in para position. The neighbouring molecules are connected via hydrogen bonds between amide groups (Fig. 1 and Table 1). Weaker hydrogen bonds can be found between methylene groups and oxygen or chlorine atoms. The arrangement of the molecules in the crystal is influenced by the C—H···π interactions between the aromatic rings (C9—H9··· C1→C6 (Cg1)) and lone pair···π interaction between the chlorine atom Cl1 and neighbouring aromatic ring C8→C13(Cg2) (the distance between Cl1 and Cg2 is 3.5871 (7) Å).

Experimental

All chemicals used were purchased from Fluka and used without further purification. The title compound was synthesized by means of method published by Ertul et al. (2009). Crystals were prepared by slow evaporation from methanol.