1,3,5-Tris(4-bromo­phen­yl)-1,3,5-triazin­ane di­chloro­methane monosolvate

Mahmoud Chebbah; Ahcene Bouchemma; Sofiane Bouacida; Leila Lefrada; Mustapha Bouhenguel

doi:10.1107/S1600536813013743

. 2013 May 25;69(Pt 6):o976. doi: 10.1107/S1600536813013743

1,3,5-Tris(4-bromophenyl)-1,3,5-triazinane dichloromethane monosolvate

Mahmoud Chebbah ^a,^b, Ahcene Bouchemma ^a,^b, Sofiane Bouacida ^c,^b,^*, Leila Lefrada ^a,^b, Mustapha Bouhenguel ^a,^b

PMCID: PMC3685111 PMID: 23795130

Abstract

In the main molecule of the title compound, C₂₁H₁₈Br₃N₃·CH₂Cl₂, the triazinane ring adopts a chair conformation with three 4-bromophenyl substituents, two in diaxial positions and the third in an equatorial arrangement (eaa). The torsion angles around the N—C bonds in the triazinane ring are in the range 55.6 (5)–60.1 (5)°. The structure can be described as being built up of alternating layers along the b axis with the CH₂Cl₂ solvent molecules sandwiched between these layers. No classical hydrogen-bonding interactions are observed in the crystal structure.

Related literature

For the conformations of 1,3,5-triaryl derivatives of 1,3,5-triazacyclohexane, see: Wellington & Tollens (1885 ▶); Bouchemma et al. (1988 ▶); Adam et al. (1993 ▶); Gilardi et al. (2003 ▶).

Experimental

Crystal data

C₂₁H₁₈Br₃N₃·CH₂Cl₂
M _r = 637.04
Triclinic,
a = 6.0588 (2) Å
b = 14.3762 (6) Å
c = 15.1617 (6) Å
α = 65.323 (3)°
β = 89.759 (2)°
γ = 80.259 (2)°
V = 1179.46 (8) Å³
Z = 2
Mo Kα radiation
μ = 5.37 mm⁻¹
T = 295 K
0.24 × 0.24 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.274, T _max = 0.467
13332 measured reflections
5637 independent reflections
3505 reflections with I > 2σ(I)
R _int = 0.078

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.145
S = 1.09
5637 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Data collection: COLLECT (Nonius, 2000) ▶; cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Click here for additional data file.^{(28.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013743/bq2386sup1.cif

e-69-0o976-sup1.cif^{(28.7KB, cif)}

Click here for additional data file.^{(270.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013743/bq2386Isup2.hkl

e-69-0o976-Isup2.hkl^{(270.4KB, hkl)}

Click here for additional data file.^{(7.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813013743/bq2386Isup3.cml

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

Acknowledgments

This work was supported by the LCATM laboratory, Université Oum El Bouaghi, Algeria. Thanks are due to MESRS and ATRST (Ministére de l’Enseignement Supérieur et de la Recherche Scientifique et l’Agence Thématique de Recherche en Sciences et Technologie - Algérie) for financial support via the PNR programme.

supplementary crystallographic information

Comment

A variety of chair, twist-boat and boat conformations can be considered for 1,3,5-triazacyclohexanes with a pyramidal arrangement of bonds at the N atoms. Four types of chair conformation. eee, eea, eaa, and aaa; where e is equatorial and a is axial, are possible and each of these conformations results in axial interactions involving substituents or lone pair of electrons on the N atoms. X-ray investigation of 1,3,5-triazacylohexane of 1,3,5-trialkyl and 1,3,5-triarylderivatives of 1,3,5-triazacyclohexane have consistently found the expected chair conformation with pyramidal arrangement of bonds at N atoms (Wellington & Tollens, 1885; Bouchemma et al., 1988; Adam et al., 1993; Gilardi et al., 2003). In the course of our studies in similar compounds we report here a conformation and crystal structure a new derivate of l,3,5-triazacylohexane, it is the product of a condensation reaction between 4-bromoaniline and formaldehyde. The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The 1,3,5-tris(p-bromorophenyl)-l,3,5-triazacylohexane, adopts a chair conformation with two p-bromophenyl substituents situated in axial positions and a third in equatorial agreement (eaa). The structure can be described as alternating layers parallel to (010)planes, along the b axis and the dichloromethane solvent molecules are sandwiched between these layers (Fig.2). The packing of (I) is stabilized by a Van Der Waals interactions which form a three-dimensional network. No classical hydrogen bond was found.

Experimental

To a solution of p-bromoaniline (25 mmol) in ethanol (10 ml), was added formaldehyde (5 ml, 37% aqueous solution). Stirring was then maintained at 25°C for 12 h. The precipitate thus formed was then collected and washed with diethyl ether. The residue was crystallized from dichloromethane.