Crystal structure of 1-[2-(2,6-di­chloro­phen­yl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

Mehmet Akkurt; Jerry P Jasinski; Shaaban K Mohamed; Adel A Marzouk; Mustafa R Albayati

doi:10.1107/S2056989015006763

. 2015 Apr 9;71(Pt 5):o299–o300. doi: 10.1107/S2056989015006763

Crystal structure of 1-[2-(2,6-dichlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

Mehmet Akkurt ^a, Jerry P Jasinski ^b, Shaaban K Mohamed ^c,^d, Adel A Marzouk ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4420112 PMID: 25995914

Abstract

The central imidazole ring of the title compound, C₂₄H₂₀Cl₂N₂O, is twisted with respect to with the planes of the 2,6-dichlorobenzene and two phenyl rings, making dihedral angles of 74.06 (18), 28.52 (17) and 67.65 (18)°, respectively. The phenyl ring not adjacent to the N-bonded 2-hydroxypropyl group shows the greatest twist, presumably to minimize steric interactions. In the crystal, molecules are linked by O—H⋯N and C—H⋯O hydrogen-bond contacts into chains along the a-axis direction. The series of parallel chains form a two-dimensional sheet approximately parallel to the bc diagonal. In addition, C—H⋯π interactions are observed between the sheets. The atoms of the 2-hydroxypropyl group and the N atom of the 1H-imidazole ring to which it is bonded are disordered over two sets of sites, with an occupancy ratio of 0.722 (5):0.278 (5). The structure was refined as an inversion twin.

Keywords: crystal structure; 1-[2-(2,6-dichlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol; imidazole ring; amino alcohol; hydrogen bonding; C—H⋯π interactions

Related literature

For similar structures and background to the biological properties of imidazole derivatives, see: Mohamed et al. (2012 ▸, 2013a ▸,b ▸); Akkurt et al. (2013 ▸); Jasinski et al. (2015 ▸).

Experimental

Crystal data

C₂₄H₂₀Cl₂N₂O
M _r = 423.32
Orthorhombic,
a = 12.1468 (4) Å
b = 8.4194 (2) Å
c = 20.9636 (7) Å
V = 2143.92 (11) Å³
Z = 4
Cu Kα radiation
μ = 2.86 mm⁻¹
T = 173 K
0.48 × 0.44 × 0.26 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T _min = 0.541, T _max = 1.000
16532 measured reflections
4076 independent reflections
3888 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.097
S = 1.05
4076 reflections
278 parameters
15 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: refined as an inversion twin
Absolute structure parameter: 0.068 (18)

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006763/sj5450sup1.cif

e-71-0o299-sup1.cif^{(603.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006763/sj5450Isup2.hkl

e-71-0o299-Isup2.hkl^{(223.6KB, hkl)}

Click here for additional data file.^{(7.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015006763/sj5450Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015006763/sj5450fig1.tif

Perspective view of the title molecule with 30% probability displacement ellipsoids. Only the major disorder component is shown.

Click here for additional data file.^{(1.9MB, tif)}

b . DOI: 10.1107/S2056989015006763/sj5450fig2.tif

The molecular packing of the title compound viewed along the b axis. H atoms not involved in the hydrogen bonding (dashed lines) have been omitted for clarity. Only the major disorder component is shown.

CCDC reference: 1057878

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg3 is the centroid of the C7C12 benzene ring.

DHA	DH	HA	D A	DHA
O1BH1BN2ⁱ	0.84	2.02	2.8468(1)	170
C14H14O1B ⁱⁱ	0.95	2.42	3.2107(1)	141
C6BH6B2Cg3ⁱⁱⁱ	0.98	2.78	3.6798(1)	154

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

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. SKM would like to thank Keene State College for providing all the X-ray data.

supplementary crystallographic information

S1. Comment

As part of an ongoing study on synthesis of imidazole based amino alcohols (Akkurt et al., 2013; Mohamed et al., 2013a,b; Jasinski et al., 2015) we report herein the synthesis and crystal structure of the title compound, 1-[2-(2,6-dichlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl] propan-2-ol.

In the title compound, Fig. 1, the central 1H-imidazole ring (N1B/N2/C1—C3) is twisted with respect to with the planes of the benzene, C7–C12, and two phenyl, C13–C18 and C19–C24, rings, making dihedral angles of 74.06 (18), 28.52 (17) and 67.65 (18)°, respectively. The dihedral angle between the C13–C18 and C19–C24 phenyl rings is 69.15 (18)°. The C7–C12 benzene ring makes dihedral angles of 87.01 (18) and 52.65 (18)° with the phenyl rings, C13–C18 and C19–C24, respectively. The bond lengths are normal and comparable to those reported for similar compounds (Mohamed et al., 2012, 2013a,b; Akkurt et al., 2013; Jasinski et al., 2015).

In the crystal, O—H···N and C—H···O hydrogen bonds (Table 1) link molecules into chains along the a axis direction and the series of parallel chains displayed in Fig. 2 form a two-dimensional sheet approximately parallel to the bc diagonal. C—H···π interactions (Table 1) are also observed in the packing of the title compound.

S2. Experimental

The title compound has been prepared according to our reported method (Jasinski et al., 2015). Irregular colourless blocks of (I) were obtained by the slow evaporation method using ethanol as a solvent. M.p. 455 K, yield, 94%.