3,22-Dioxa-11,14-di­aza­penta­cyclo­[12.8.0.02,11.05,10.015,20]docosa-5(10),6,8,15(20),16,18-hexa­ene-4,21-dione

Xiaolin Ren; Jiao Feng; Jinglin Wang; Bin Liu; Binsheng Yang

doi:10.1107/S1600536813024537

. 2013 Sep 12;69(Pt 10):o1535. doi: 10.1107/S1600536813024537

3,22-Dioxa-11,14-diazapentacyclo[12.8.0.0^2,11.0^5,10.0^15,20]docosa-5(10),6,8,15(20),16,18-hexaene-4,21-dione

Xiaolin Ren ^a, Jiao Feng ^a, Jinglin Wang ^b, Bin Liu ^a, Binsheng Yang ^a,^*

PMCID: PMC3790403 PMID: 24098222

Abstract

In the title compound, C₁₈H₁₄N₂O₄, the piperazine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 13.09 (9)°. In the crystal, molecules are linked along the c axis by C—H⋯π and N⋯π [H(N)–centroid distances = 2.8030 (2) and 3.376 (2) Å] interactions between neighbouring molecules.

Related literature

For applications of π–π interactions, see: Janiak (2000 ▶). For C—H⋯π interactions, see: Ciunik & Desiraju (2001 ▶) and for N⋯π interactions, see: Lindeman et al. (1998 ▶). For the synthesis of the 2,2′-(ethane-1,2-diylbis(azanediyl))dibenzoic acid precursor, see: Berger & Telford (2002 ▶).

Experimental

Crystal data

C₁₈H₁₄N₂O₄
M _r = 322.31
Triclinic,
a = 8.058 (1) Å
b = 8.2629 (11) Å
c = 12.0972 (14) Å
α = 74.956 (2)°
β = 73.868 (1)°
γ = 72.311 (1)°
V = 723.54 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.23 × 0.20 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.976, T _max = 0.986
3858 measured reflections
2533 independent reflections
1301 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.098
S = 1.01
2533 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813024537/ff2118sup1.cif

e-69-o1535-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024537/ff2118Isup2.hkl

e-69-o1535-Isup2.hkl^{(124.4KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813024537/ff2118Isup3.cml

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

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

Cg1 is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1ⁱ	0.98	2.80	3.7337 (3)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (Nos. 21271122 and 20901048) and Shanxi Scholarship Council of China (2013–018).

supplementary crystallographic information

1. Comment

The C–H···π and π–π interactions are important noncovalent intermolecular forces in determining the crystal packing, molecular assemblies, and structures of large biological systems (Janiak, 2000). In the present work, the crystal of the title compound is generated by noncovalent interactions.

In the title molecule (Fig. 1), the piperazine ring adopts a chair conformation and the dihedral angle between two phenyl rings (C6—C11; C13—C18) is 13.09 (9)°.

As shown in Figure 2, the neighboring molecules of title compound are arranged in a mutual head-to-tail manner by C–H···Cg1ⁱ (Cg1 is the centroid of the C6—C11 benzene ring) interactions (black dotted lines) and N···Cg2ⁱⁱ (Cg2 is the centroid of the C13—C18 benzene ring) interactions (pink dotted lines)to form infinite one-dimensional chain structure along the c axis [symmetry code: (i) 1 - x, 1 - y,1 - z; (ii)1 - x, 1 - y, 2 - z].

The adjacent one-dimensional chains, by van der Waals contacts, stack in a side-by-side fashion along the c axis to form three-dimensional structure (Fig. 3).

2. Experimental

The precursor 2,2'-(ethane-1,2-diylbis(azanediyl))dibenzoic acid (EDA) was synthesized according to literature procedures (Berger et al., 2002). The title compound was prepared by stirring a methanolic solution of EDA (300 mg, 1.0 mmol) and triethylamine (1 ml) for 10 min at room temperature. Then, 10 ml of a methanol solution containing CuCl₂·2H₂O(170 mg, 1 mmol) was added to the mixture and refluxed for 2 h. The mixture was filtered and washed with methanol. The EDA-Cu compound is not achieved as predicted. However, orange single crystals of the title complex suitable for X-ray analysis were obtained after several days from the mother liquor by slow evaporation.