3-Amino-5,5-di­phenyl­imidazolidine-2,4-dione

Joel T Mague; Alaa A-M Abdel-Aziz; Adel S El-Azab

doi:10.1107/S1600536814002487

. 2014 Feb 8;70(Pt 3):o262–o263. doi: 10.1107/S1600536814002487

3-Amino-5,5-diphenylimidazolidine-2,4-dione

Joel T Mague ^a,^*, Alaa A-M Abdel-Aziz ^b,^c,^‡, Adel S El-Azab ^b,^d

PMCID: PMC3998397 PMID: 24764978

Abstract

The title compound, C₁₅H₁₃N₃O₂, crystallizes with two independent molecules in the asymmetric unit, which differ considerably in the dihedral angles made between the phenyl groups and the five-membered rings [47.19 (8) and 61.16 (9)° in one molecule and 55.04 (10) and 55.00 (8)° in the other]. In the crystal, N—H⋯O hydrogen bonds generate columnar units having approximate fourfold rotational symmetry about axes parallel to b.

Related literature

For the biological properties of hydantoins, see: El-Deeb et al. (2010 ▶); Rajic et al. (2006 ▶); Carmi et al. (2006 ▶); Sergent et al. (2008 ▶). For the preparation of the title compound, see: Kiec-Kononowicz et al. (1984 ▶). For related crystal structures, see: Delgado et al. (2007 ▶); Roszak & Weaver (1998 ▶); Kashif et al. (2008 ▶); Coquerel et al. (1993 ▶); SethuSankar et al. (2002 ▶); Eknoian et al. (1999 ▶); Ciechanowicz-Rutkowska et al. (1994 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃O₂
M _r = 267.28
Monoclinic,
a = 20.1565 (7) Å
b = 6.1651 (2) Å
c = 20.3250 (7) Å
β = 97.781 (2)°
V = 2502.47 (15) Å³
Z = 8
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 100 K
0.22 × 0.07 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T _min = 0.84, T _max = 0.96
32772 measured reflections
4560 independent reflections
3185 reflections with I > 2σ(I)
R _int = 0.105

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.111
S = 1.08
4560 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002487/sj5389sup1.cif

e-70-0o262-sup1.cif^{(1,014.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002487/sj5389Isup2.hkl

e-70-0o262-Isup2.hkl^{(250.1KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814002487/sj5389Isup3.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=984860

Additional supporting information: 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⋯O1ⁱ	0.91	1.92	2.828 (3)	177
N3—H3A⋯O3	0.91	2.11	2.957 (3)	154
N4—H4⋯O4ⁱⁱ	0.91	1.91	2.820 (3)	176
N6—H6A⋯O3ⁱ	0.91	2.58	3.320 (3)	139
N6—H6B⋯O2ⁱⁱⁱ	0.91	2.46	3.070 (3)	124
N6—H6B⋯N3ⁱⁱⁱ	0.91	2.52	3.363 (3)	154

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

Acknowledgments

The authors extend their appreciation to the Research Center of Pharmacy, King Saud University, for funding this work. The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged as is the Chemistry Department of Tulane University for support of the Tulane Crystallography Laboratory.

supplementary crystallographic information

1. Comment

Hydantoins are an important class of compounds which have long attracted attention, owing to their remarkable biological and pharmacological properties. These include antitumor and antiviral activity, insulinotropic properties and use as EGFR inhibitors. (El-Deeb et al., 2010; Rajic et al., 2006; Carmi et al., 2006; Sergent et al., 2008). Of several structure determinations of hydantoins (Delgado et al., 2007; Kashif et al., 2008; Coquerel et al., 1993; SethuSankar et al., 2002; Ciechanowicz-Rutkowska et al., 1994; Roszak & Weaver, 1998; Eknoian et al., 1999), those in the last two reports bear the greatest similarity to the title compound. The title compound crystallizes with two independent molecules (A and B) in the asymmetric unit. The 5-membered ring in A is planar to within 0.032 Å while that in B is planar to within 0.016 Å. Molecules A and B differ most notably in the dihedral angles which the pendant phenyl rings make with the 5-membered ring. For molecule A the angles for C4/C5/C6/C7/C8/C9 and for C10/C11/C12/C13/C14/C15 are, respectively, 47.19 (8) and 61.16 (9)°. In molecule B the angles for C19/C20/C21/C22/C23/C24 and for C25/C26/C27/C28/C29/C30 are identical at 55.04 (10) and 55.00 (8)°, respectively. Both the imino and amino groups participate in intermolecular N—H···O hydrogen bonding which forms columns having approximate 4-fold rotational symmetry about axes parallel to b (Table 1 and Fig. 2).

2. Experimental

The title compound, 3-amino-5,5-diphenylimidazolidine-2,4-dione, was successfully obtained by the reaction of 5,5-diphenylhydantoin and hydrazine hydrate following the published route (Kiec-Kononowicz et al., 1984).