Diethyl 1,4-dioxo-1,2,2a,3,4,10b-hexahydro-5H,10H-2,3,4a,10a-tetraaza­benzo[g]cyclopenta[cd]azulene-2a,10b-dicarboxylate

Jing Qin

doi:10.1107/S1600536809014548

. 2009 Apr 25;65(Pt 5):o1100. doi: 10.1107/S1600536809014548

Diethyl 1,4-dioxo-1,2,2a,3,4,10b-hexahydro-5H,10H-2,3,4a,10a-tetraazabenzo[g]cyclopenta[cd]azulene-2a,10b-dicarboxylate

Jing Qin ^a,^*

PMCID: PMC2977778 PMID: 21583914

Abstract

In the title compound, C₁₈H₂₀N₄O₆, the dihedral angle between the two fused five-membered rings in the glycoluril unit is 64.42 (2)°. The crystal structure features intermolecular N—H⋯O and C—H⋯O interactions. An intramolecular C—H⋯O contact is also present.

Related literature

For the preparation of the title compound, see: Wu et al. (2002a ▶). For crystal engineering studies of glycoluril and its derivatives, see: Chen et al. (2007 ▶); Wang et al. (2006 ▶); Johnson et al. (2002 ▶); Wu et al. (2002b ▶).

Experimental

Crystal data

C₁₈H₂₀N₄O₆
M _r = 388.38
Triclinic,
a = 8.1394 (5) Å
b = 9.4425 (5) Å
c = 13.3576 (8) Å
α = 93.1550 (10)°
β = 96.0560 (10)°
γ = 112.3970 (10)°
V = 938.80 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T _min = 0.976, T _max = 0.989
7700 measured reflections
3624 independent reflections
3028 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.144
S = 1.05
3624 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014548/nc2142sup1.cif

e-65-o1100-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014548/nc2142Isup2.hkl

e-65-o1100-Isup2.hkl^{(177.7KB, 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
C7—H7A⋯O3	0.97	2.52	3.107 (2)	119
C17—H17B⋯O2ⁱ	0.97	2.58	3.343 (3)	136
C7—H7B⋯O3ⁱⁱ	0.97	2.59	3.478 (2)	153
N4—H4A⋯O2ⁱⁱⁱ	0.85 (3)	2.05 (3)	2.871 (2)	165 (2)
N3—H3A⋯O5^iv	0.87 (3)	2.09 (3)	2.917 (2)	159 (2)

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

Acknowledgments

The author gratefully acknowledges support from Central China Normal University.

supplementary crystallographic information

Comment

Glycoluril and its derivatives have been widely studied in supramolecular chemistry (Johnson et al., 2002; Wu et al., 2002b). As a continuation of our recent studies in this area (Wang et al., 2006; Chen et al., 2007), we herein report the crystal structure of the title compound (Fig. 1). The dihedral angle between the two fused five-membered rings in the glycoluril unit is 64.42 (2) °. In the crystal structure the molecules are connected via weak intermolecular N—H···O hydrogen bonding (Table 1).

Experimental

The title compound was synthesized according to a literature procedure (Wu et al.; 2002a). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (1:2) solution of the title compound at room temperature.