Crystal structure of 4-[1-(2-hy­droxy­prop­yl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid

Jerry P Jasinski; Shaaban K Mohamed; Mehmet Akkurt; Antar A Abdelhamid; Mustafa R Albayati

doi:10.1107/S2056989014027078

. 2015 Jan 3;71(Pt 2):o77–o78. doi: 10.1107/S2056989014027078

Crystal structure of 4-[1-(2-hydroxypropyl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid

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

PMCID: PMC4384621 PMID: 25878880

Abstract

In the title compound, C₂₅H₂₂N₂O₃, the central imidazole ring makes dihedral angles of 48.43 (10), 20.23 (10) and 75.38 (11)° with the benzene ring and the two phenyl rings, respectively. The phenyl ring 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, O—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network. In addition, C—H⋯π interactions are also observed.

Keywords: crystal structure; 4-[1-(2-hydroxypropyl)-4,5-diphenyl-1H-imidazol-2-yl]benzoic acid; imidazole ring; amino alcohol

Related literature

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

Experimental

Crystal data

C₂₅H₂₂N₂O₃
M _r = 398.45
Triclinic,
a = 6.8710 (4) Å
b = 10.7188 (6) Å
c = 14.9178 (7) Å
α = 103.569 (4)°
β = 93.094 (4)°
γ = 105.878 (5)°
V = 1019.03 (10) Å³
Z = 2
Cu Kα radiation
μ = 0.69 mm⁻¹
T = 293 K
0.36 × 0.32 × 0.24 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T _min = 0.928, T _max = 1.000
6591 measured reflections
3859 independent reflections
3209 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.136
S = 1.02
3859 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▸); 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/S2056989014027078/hb7338sup1.cif

e-71-00o77-sup1.cif^{(29.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027078/hb7338Isup2.hkl

e-71-00o77-Isup2.hkl^{(211.7KB, hkl)}

Click here for additional data file.^{(7.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989014027078/hb7338Isup3.cml

Click here for additional data file.^{(1.4MB, tif)}

. DOI: 10.1107/S2056989014027078/hb7338fig1.tif

Perspective view of the title molecule with 50% probability ellipsoids.

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989014027078/hb7338fig2.tif

View of a part of the hydrogen bonding in the title compound

CCDC reference: 1038591

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

Table 1. Hydrogen-bond geometry (, ).

Cg1 is the centroid of the N1/N2/C1C3 ring.

DHA	DH	HA	D A	DHA
O2H2O3ⁱ	0.82	1.86	2.6718(17)	170
O3H3N1ⁱⁱ	0.82	2.04	2.8377(19)	166
C19H19BO1ⁱⁱⁱ	0.96	2.46	3.355(3)	155
C24H24O2^iv	0.93	2.57	3.482(3)	167
C19H19C Cg1ⁱⁱ	0.96	2.53	3.422(2)	154

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

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. Also, SKM would like to thank Keene State College for providing all X-ray data and Manchester Metropolitan University for supporting this study.

supplementary crystallographic information

S1. Comment

Following to our ongoing study on synthesis of imidazole based amino alcohols (Akkurt et al., 2013; Mohamed et al., 2013a,b) we herein report the synthesis and crystal structure of the title compound.

In the title compound, Fig. 1, the central 1H-imidazole ring (N1/N2/C1—C3) makes dihedral angles of 48.43 (10), 20.23 (10) and 75.38 (11)°, with the benzene ring (C10–C15) and two phenyl rings (C4–C9 and C20–C25), respectively. The dihedral angle between the (C4–C9 and C20–C25) phenyl rings is 69.94 (11)°. The (C10–C15) benzene ring forms dihedral angles of 36.05 (10) and 35.91 (10)° with two the phenyl rings (C4–C9 and C20–C25), respectively. The bond lengths are comparable to those reported for similar compounds reported in the literature (Akkurt et al., 2013; Mohamed et al., 2013a,b).

In the crystal, O—H···N, O—H···O and C—H···O hydrogen bonds link the adjacent molecules, into a three dimensional network structure (Table 1, Fig. 2). Furthermore, 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 (Mohamed et al., 2012). Irregular colourless chunks of (I) were obtained by the slow evaporation method using ethanol as a solvent. M.p. 456 K.