organic compounds
2-(1H-Benzimidazol-2-yl)phenol
aResearch and Development Center, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, bDepartment of Chemistry, Annamaliar College of Engineering, Mudaiyur 606 902, Tamilnadu, India, cPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and dDepartment of Chemistry, S.K.P. Engineering College, Thiruvannamalai 606 611, Tamilnadu, India
*Correspondence e-mail: thiruvalluvar.a@gmail.com
The title molecule, C13H10N2O, is essentially planar, the maximum deviation from the plane of the non-H atoms being 0.016 (2) Å. The imidazole ring makes a dihedral angle of 0.37 (13)° with the attached benzene ring. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains propagating in [001]. The crystal packing also features four π–π stacking interactions involving the imidazole ring, fused benzene ring and attached benzene ring system [centroid–centroid distances = 3.6106 (17), 3.6108 (17), 3.6666 (17) and 3.6668 (17) Å].
CCDC reference: 982320
Related literature
For applications and general background to substituted benzimidazole derivatives, see: Nakamura et al. (2004); Su Han & Kim (2001); Roman et al. 2007; Congiu et al. 2008. For related crystal structures, see: Han (2010); Zhan et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). Note added in proof: a low temperature determination of the same structure has been reported [Konoshima, H., Nagao, S., Kiyota, I., Amimoto, K., Yamamoto, N., Sekine, M., Nakata, M., Furukawa, K. & Sekiya, H. (2012). Phys. Chem. Chem. Phys. 14, 16448–16457].
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 and PLATON.
Supporting information
CCDC reference: 982320
10.1107/S1600536814001366/hg5377sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001366/hg5377Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001366/hg5377Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536814001366/hg5377Isup4.cml
To the pure o-phenylenediamine (1.6 g, 15 mmol) in ethanol (10 ml), 2-hydroxybenzaldehyde (1.6 g, 15 mmol) and ammonium acetate (3 g) was added about 1 h by maintaining the temperature at 353 K. The reaction mixture was refluxed for 48 hrs and extracted with dichloromethane. The solid separated was purified by
using benzene as the Yield: 1.89 g; 60%. The compound was dissolved in benzene and ethyl acetate (9:1) mixture and allowed to slow evaporation for two days, to obtain crystals suitable for X-ray diffraction studies.The N-bound H atom was located in a difference Fourier map and refined freely; N1—H1 = 0.91 (2) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H = 0.82 and Csp2—H = 0.93 Å. Uiso(H) = 1.5Ueq(O) and 1.2Ueq(C).
Imidazole derivatives have occupied a unique place in the field of medicinal chemistry. Many of the substituted imidazoles are known as inhibitors of P38 map kinase, fungicides and herbicides and therapeutic agents (Nakamura et al., 2004; Su Han & Kim, 2001). Being a polar and ionisable aromatic compounds, it improves pharmacokinetic characteristics of lead molecules and thus used as a remedy to optimize solubility and bioavailability parameters of proposed poorly soluble lead molecules. The imidazole ring is a constituent of several important natural products, including purine, histamine, histidine and nucleic acid (Roman et al., 2007; Congiu et al., 2008). Owing to the wide range of pharmacological and biological activities, the synthesis of imidazoles has become an important target in current years. We are interested to study the biological and photo physical properties of 2-(1H-benzimidazol-2-yl)phenol. The related compounds whose structures have been solved by X-ray are 2-(1H-Benzimidazol-2-yl)-4,6-dichlorophenol (Han, 2010) and 4-(1H-Benzo[d]imidazol-2-yl)phenol (Zhan et al., 2007). As part of our research, we have synthesized the title compound and report its
here.The title molecule, C13H10N2O, (Fig. 1), is essentially planar, the maximum deviation from the plane of the non-H atoms being 0.016 (2) Å for O26. The imidazole ring (N1/C2/N3/C9/C8) makes dihedral angle of 0.37 (13)° with the attached benzene ring (C21—C26).
An intramolecular O26—H26···N3 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). In the crystal, symmetry-related molecules are linked through N1—H1···O26 hydrogen bonds, forming an one dimensional chains propagating in [001] (Fig. 2).
The crystal packing also features four π-π stacking interactions. [Cg1—Cg2i = 3.6668 (17) Å, Cg1—Cg3ii = 3.6106 (17) Å, Cg2—Cg1ii = 3.6666 (17) Å and Cg3—Cg1i = 3.6108 (17) Å, symmetry codes (i): x, 1 + y, z; (ii): x, -1 + y, z. Where, Cg1 is the centroid of the imidazole ring (N1/C2/N3/C9/C8), Cg2 is the centroid of the fused benzene ring (C4—C9) and Cg3 is the centroid of the attached benzene ring (C21—C26) respectively] (Fig. 3). The N—C, C═N, Car—Car and C—O bond lengths in (I) are within their normal ranges (Allen et al., 1987).
For applications and general background to substituted benzimidazole derivatives, see: Nakamura et al. (2004); Su Han & Kim (2001); Roman et al. 2007; Congiu et al. 2008. For related crystal structures, see: Han (2010); Zhan et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).C13H10N2O | F(000) = 440 |
Mr = 210.23 | Dx = 1.380 Mg m−3 |
Monoclinic, P21/c | Melting point: 386 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.864 (4) Å | Cell parameters from 612 reflections |
b = 4.7431 (8) Å | θ = 4.8–23.8° |
c = 12.952 (2) Å | µ = 0.09 mm−1 |
β = 102.34 (2)° | T = 293 K |
V = 1012.1 (3) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.30 × 0.25 mm |
Agilent Xcalibur Eos Gemini diffractometer | 2338 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1184 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 16.3291 pixels mm-1 | θmax = 29.2°, θmin = 3.2° |
ω scans | h = −23→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −3→6 |
Tmin = 0.829, Tmax = 1.000 | l = −15→17 |
4073 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: mixed |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0339P)2] where P = (Fo2 + 2Fc2)/3 |
2338 reflections | (Δ/σ)max < 0.001 |
150 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C13H10N2O | V = 1012.1 (3) Å3 |
Mr = 210.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.864 (4) Å | µ = 0.09 mm−1 |
b = 4.7431 (8) Å | T = 293 K |
c = 12.952 (2) Å | 0.30 × 0.30 × 0.25 mm |
β = 102.34 (2)° |
Agilent Xcalibur Eos Gemini diffractometer | 2338 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 1184 reflections with I > 2σ(I) |
Tmin = 0.829, Tmax = 1.000 | Rint = 0.037 |
4073 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.18 e Å−3 |
2338 reflections | Δρmin = −0.17 e Å−3 |
150 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | ||
O26 | 0.20929 (12) | 0.7018 (4) | 0.54707 (12) | 0.0640 (8) | |
N1 | 0.25872 (13) | 0.5474 (4) | 0.25071 (16) | 0.0459 (8) | |
N3 | 0.28328 (12) | 0.4482 (4) | 0.42170 (14) | 0.0448 (7) | |
C2 | 0.24046 (15) | 0.6055 (5) | 0.34606 (18) | 0.0420 (8) | |
C4 | 0.38923 (16) | 0.0807 (5) | 0.4149 (2) | 0.0561 (10) | |
C5 | 0.42862 (16) | −0.0543 (5) | 0.3475 (2) | 0.0603 (11) | |
C6 | 0.41275 (17) | 0.0093 (6) | 0.2410 (2) | 0.0621 (11) | |
C7 | 0.35740 (17) | 0.2089 (5) | 0.1985 (2) | 0.0554 (10) | |
C8 | 0.31718 (15) | 0.3444 (5) | 0.26679 (19) | 0.0438 (9) | |
C9 | 0.33257 (15) | 0.2825 (5) | 0.37415 (18) | 0.0434 (9) | |
C21 | 0.18120 (15) | 0.8077 (4) | 0.36215 (19) | 0.0424 (8) | |
C22 | 0.13653 (15) | 0.9671 (5) | 0.28084 (19) | 0.0512 (9) | |
C23 | 0.08097 (17) | 1.1585 (5) | 0.2980 (2) | 0.0614 (11) | |
C24 | 0.06758 (18) | 1.1945 (5) | 0.3980 (3) | 0.0640 (11) | |
C25 | 0.11064 (18) | 1.0406 (5) | 0.4800 (2) | 0.0617 (11) | |
C26 | 0.16741 (16) | 0.8493 (5) | 0.4634 (2) | 0.0485 (9) | |
H1 | 0.2390 (15) | 0.643 (5) | 0.190 (2) | 0.068 (9)* | |
H4 | 0.40039 | 0.03737 | 0.48660 | 0.0673* | |
H5 | 0.46693 | −0.19179 | 0.37380 | 0.0722* | |
H6 | 0.44063 | −0.08687 | 0.19714 | 0.0748* | |
H7 | 0.34708 | 0.25216 | 0.12684 | 0.0666* | |
H22 | 0.14474 | 0.94254 | 0.21266 | 0.0613* | |
H23 | 0.05206 | 1.26504 | 0.24222 | 0.0737* | |
H24 | 0.02909 | 1.32393 | 0.40988 | 0.0768* | |
H25 | 0.10138 | 1.06568 | 0.54762 | 0.0741* | |
H26 | 0.23899 | 0.58738 | 0.52659 | 0.0960* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O26 | 0.0835 (16) | 0.0762 (13) | 0.0334 (11) | 0.0152 (10) | 0.0147 (10) | −0.0050 (9) |
N1 | 0.0540 (15) | 0.0546 (13) | 0.0295 (12) | −0.0037 (11) | 0.0100 (10) | 0.0028 (11) |
N3 | 0.0511 (14) | 0.0521 (12) | 0.0304 (11) | 0.0005 (11) | 0.0070 (10) | −0.0010 (10) |
C2 | 0.0486 (16) | 0.0465 (14) | 0.0314 (14) | −0.0094 (12) | 0.0095 (12) | −0.0032 (12) |
C4 | 0.0567 (19) | 0.0620 (17) | 0.0475 (17) | 0.0017 (14) | 0.0068 (14) | −0.0017 (14) |
C5 | 0.0532 (18) | 0.0608 (17) | 0.067 (2) | 0.0028 (14) | 0.0129 (15) | −0.0089 (16) |
C6 | 0.062 (2) | 0.0648 (17) | 0.067 (2) | −0.0066 (16) | 0.0304 (16) | −0.0132 (16) |
C7 | 0.067 (2) | 0.0610 (17) | 0.0436 (17) | −0.0111 (16) | 0.0241 (15) | −0.0073 (14) |
C8 | 0.0454 (16) | 0.0462 (14) | 0.0410 (15) | −0.0080 (13) | 0.0122 (12) | −0.0022 (12) |
C9 | 0.0443 (16) | 0.0488 (14) | 0.0370 (15) | −0.0055 (13) | 0.0087 (12) | −0.0015 (12) |
C21 | 0.0454 (16) | 0.0424 (13) | 0.0391 (15) | −0.0070 (12) | 0.0087 (12) | −0.0033 (12) |
C22 | 0.0537 (17) | 0.0547 (15) | 0.0440 (17) | −0.0030 (14) | 0.0081 (13) | 0.0020 (13) |
C23 | 0.0558 (19) | 0.0583 (17) | 0.067 (2) | 0.0025 (15) | 0.0062 (16) | 0.0056 (15) |
C24 | 0.0547 (19) | 0.0539 (16) | 0.085 (2) | 0.0048 (14) | 0.0187 (17) | −0.0042 (17) |
C25 | 0.067 (2) | 0.0645 (18) | 0.059 (2) | 0.0004 (16) | 0.0255 (16) | −0.0112 (15) |
C26 | 0.0534 (18) | 0.0508 (15) | 0.0410 (16) | −0.0033 (13) | 0.0092 (13) | −0.0051 (13) |
O26—C26 | 1.355 (3) | C21—C26 | 1.394 (4) |
O26—H26 | 0.8200 | C21—C22 | 1.382 (3) |
N1—C2 | 1.363 (3) | C22—C23 | 1.357 (4) |
N1—C8 | 1.362 (3) | C23—C24 | 1.372 (5) |
N3—C9 | 1.381 (3) | C24—C25 | 1.363 (4) |
N3—C2 | 1.317 (3) | C25—C26 | 1.369 (4) |
N1—H1 | 0.91 (2) | C4—H4 | 0.9300 |
C2—C21 | 1.432 (3) | C5—H5 | 0.9300 |
C4—C9 | 1.376 (4) | C6—H6 | 0.9300 |
C4—C5 | 1.364 (4) | C7—H7 | 0.9300 |
C5—C6 | 1.381 (4) | C22—H22 | 0.9300 |
C6—C7 | 1.361 (4) | C23—H23 | 0.9300 |
C7—C8 | 1.383 (4) | C24—H24 | 0.9300 |
C8—C9 | 1.390 (3) | C25—H25 | 0.9300 |
C26—O26—H26 | 109.00 | C22—C23—C24 | 119.8 (2) |
C2—N1—C8 | 107.5 (2) | C23—C24—C25 | 120.1 (3) |
C2—N3—C9 | 106.09 (19) | C24—C25—C26 | 120.4 (3) |
C8—N1—H1 | 127.3 (16) | O26—C26—C21 | 121.1 (2) |
C2—N1—H1 | 124.9 (16) | O26—C26—C25 | 118.6 (2) |
N1—C2—N3 | 111.4 (2) | C21—C26—C25 | 120.3 (2) |
N1—C2—C21 | 124.5 (2) | C5—C4—H4 | 121.00 |
N3—C2—C21 | 124.0 (2) | C9—C4—H4 | 121.00 |
C5—C4—C9 | 118.3 (2) | C4—C5—H5 | 119.00 |
C4—C5—C6 | 121.3 (2) | C6—C5—H5 | 119.00 |
C5—C6—C7 | 121.7 (3) | C5—C6—H6 | 119.00 |
C6—C7—C8 | 116.9 (2) | C7—C6—H6 | 119.00 |
N1—C8—C7 | 132.0 (2) | C6—C7—H7 | 122.00 |
C7—C8—C9 | 122.0 (2) | C8—C7—H7 | 122.00 |
N1—C8—C9 | 106.1 (2) | C21—C22—H22 | 119.00 |
C4—C9—C8 | 119.8 (2) | C23—C22—H22 | 119.00 |
N3—C9—C8 | 108.9 (2) | C22—C23—H23 | 120.00 |
N3—C9—C4 | 131.3 (2) | C24—C23—H23 | 120.00 |
C2—C21—C22 | 122.6 (2) | C23—C24—H24 | 120.00 |
C2—C21—C26 | 119.6 (2) | C25—C24—H24 | 120.00 |
C22—C21—C26 | 117.8 (2) | C24—C25—H25 | 120.00 |
C21—C22—C23 | 121.6 (2) | C26—C25—H25 | 120.00 |
C8—N1—C2—N3 | −0.8 (3) | C6—C7—C8—N1 | −179.1 (3) |
C8—N1—C2—C21 | −179.7 (2) | C6—C7—C8—C9 | 0.5 (4) |
C2—N1—C8—C7 | 180.0 (3) | N1—C8—C9—N3 | 0.1 (3) |
C2—N1—C8—C9 | 0.4 (3) | N1—C8—C9—C4 | 179.5 (2) |
C9—N3—C2—N1 | 0.8 (3) | C7—C8—C9—N3 | −179.6 (2) |
C9—N3—C2—C21 | 179.7 (2) | C7—C8—C9—C4 | −0.1 (4) |
C2—N3—C9—C4 | −179.9 (3) | C2—C21—C22—C23 | −179.7 (2) |
C2—N3—C9—C8 | −0.6 (3) | C26—C21—C22—C23 | 0.1 (4) |
N1—C2—C21—C22 | −0.4 (4) | C2—C21—C26—O26 | 0.1 (4) |
N1—C2—C21—C26 | 179.9 (2) | C2—C21—C26—C25 | −179.6 (2) |
N3—C2—C21—C22 | −179.2 (2) | C22—C21—C26—O26 | −179.6 (2) |
N3—C2—C21—C26 | 1.1 (4) | C22—C21—C26—C25 | 0.7 (4) |
C9—C4—C5—C6 | 0.3 (4) | C21—C22—C23—C24 | −0.7 (4) |
C5—C4—C9—N3 | 179.0 (3) | C22—C23—C24—C25 | 0.7 (4) |
C5—C4—C9—C8 | −0.3 (4) | C23—C24—C25—C26 | 0.0 (4) |
C4—C5—C6—C7 | 0.1 (4) | C24—C25—C26—O26 | 179.6 (2) |
C5—C6—C7—C8 | −0.4 (4) | C24—C25—C26—C21 | −0.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O26i | 0.91 (2) | 1.96 (3) | 2.851 (3) | 169 (2) |
O26—H26···N3 | 0.82 | 1.81 | 2.551 (3) | 150 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O26i | 0.91 (2) | 1.96 (3) | 2.851 (3) | 169 (2) |
O26—H26···N3 | 0.82 | 1.81 | 2.551 (3) | 150 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Acknowledgements
SMP thanks Annamaliar College of Engineering, Mudaiyur, for providing constant support for this research study. NS is thankful to S·K.P. Engineering College, Thiruvannamalai, for providing constant support for this research work.
References
Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Mallamo, M., Mazzone, A., Polidori, G. & Spagna, R. (2012). J. Appl. Cryst. 45, 357–361. Web of Science CrossRef CAS IUCr Journals Google Scholar
Congiu, C., Cocco, M. T. & Onnis, V. (2008). Bioorg. Med. Chem. Lett. 18, 989–993. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Han, L.-L. (2010). Acta Cryst. E66, o2047. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nakamura, T., Kakinuma, H., Umemiya, H., Amada, H., Miyata, N., Taniguchi, K., Bando, K. & Sato, M. (2004). Bioorg. Med. Chem. Lett. 14, 333–336. Web of Science CrossRef PubMed CAS Google Scholar
Roman, G., Riley, J. G., Vlahakis, J. Z., Kinobe, R. T., Brien, J. F., Nakatsu, K. & Szarek, W. A. (2007). Bioorg. Med. Chem. 15, 3225–3234. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Su Han, M. & Kim, D. H. (2001). Bioorg. Med. Chem. Lett. 11, 1425–1427. Web of Science PubMed Google Scholar
Zhan, Q.-G., Liu, M.-S., Zeng, R.-H., Yang, D.-Q. & Cai, Y.-P. (2007). Acta Cryst. E63, o3470. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Imidazole derivatives have occupied a unique place in the field of medicinal chemistry. Many of the substituted imidazoles are known as inhibitors of P38 map kinase, fungicides and herbicides and therapeutic agents (Nakamura et al., 2004; Su Han & Kim, 2001). Being a polar and ionisable aromatic compounds, it improves pharmacokinetic characteristics of lead molecules and thus used as a remedy to optimize solubility and bioavailability parameters of proposed poorly soluble lead molecules. The imidazole ring is a constituent of several important natural products, including purine, histamine, histidine and nucleic acid (Roman et al., 2007; Congiu et al., 2008). Owing to the wide range of pharmacological and biological activities, the synthesis of imidazoles has become an important target in current years. We are interested to study the biological and photo physical properties of 2-(1H-benzimidazol-2-yl)phenol. The related compounds whose structures have been solved by X-ray are 2-(1H-Benzimidazol-2-yl)-4,6-dichlorophenol (Han, 2010) and 4-(1H-Benzo[d]imidazol-2-yl)phenol (Zhan et al., 2007). As part of our research, we have synthesized the title compound and report its crystal structure here.
The title molecule, C13H10N2O, (Fig. 1), is essentially planar, the maximum deviation from the plane of the non-H atoms being 0.016 (2) Å for O26. The imidazole ring (N1/C2/N3/C9/C8) makes dihedral angle of 0.37 (13)° with the attached benzene ring (C21—C26).
An intramolecular O26—H26···N3 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). In the crystal, symmetry-related molecules are linked through N1—H1···O26 hydrogen bonds, forming an one dimensional chains propagating in [001] (Fig. 2).
The crystal packing also features four π-π stacking interactions. [Cg1—Cg2i = 3.6668 (17) Å, Cg1—Cg3ii = 3.6106 (17) Å, Cg2—Cg1ii = 3.6666 (17) Å and Cg3—Cg1i = 3.6108 (17) Å, symmetry codes (i): x, 1 + y, z; (ii): x, -1 + y, z. Where, Cg1 is the centroid of the imidazole ring (N1/C2/N3/C9/C8), Cg2 is the centroid of the fused benzene ring (C4—C9) and Cg3 is the centroid of the attached benzene ring (C21—C26) respectively] (Fig. 3). The N—C, C═N, Car—Car and C—O bond lengths in (I) are within their normal ranges (Allen et al., 1987).