2-(4-Phenyl-3H-1,5-benzodiazepin-2-yl)phenol

Feng-Ke Yang; Wei Cheng; Yi-Ning Ding

doi:10.1107/S1600536808034752

. 2008 Nov 8;64(Pt 12):o2278. doi: 10.1107/S1600536808034752

2-(4-Phenyl-3H-1,5-benzodiazepin-2-yl)phenol

Feng-Ke Yang ^a,^*, Wei Cheng ^a, Yi-Ning Ding ^b

PMCID: PMC2960137 PMID: 21581258

Abstract

In the title compound, C₂₁H₁₆N₂O, the dihedral angle between the pendant aromatic rings is 74.2–(1)°.. The conformation is stabilized by an intramolecular O—H⋯N hydrogen bond.

Related literature

For the biological properties of Schiff bases, see: Abu-Hussen (2006 ▶); Mladenova et al. (2002 ▶); Singh et al. (2006 ▶). For the applications of nitrogen heterocyclic compounds, see: Adsule et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₁₆N₂O
M _r = 312.36
Monoclinic,
a = 6.3787 (13) Å
b = 16.695 (3) Å
c = 16.166 (4) Å
β = 110.72 (3)°
V = 1610.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: none
6422 measured reflections
2806 independent reflections
1726 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.099
wR(F ²) = 0.198
S = 1.18
2806 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034752/at2658sup1.cif

e-64-o2278-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034752/at2658Isup2.hkl

e-64-o2278-Isup2.hkl^{(137.8KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.83	1.82	2.563 (5)	147

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

Acknowledgments

The authors thank the Natural Science Foundation of Shandong Province (No.Q2006B02).

supplementary crystallographic information

Comment

Monocondensed Schiff bases use as intermediates, in the synthesis of unsymmetrical multidentate Schiff base lingands. So they are attractive. Schiff bases often exhibit important biological activities such as antifungal (Singh et al., 2006), antibacterial (Abu-Hussen et al., 2006) and antitumor (Mladenova et al., 2002). Nitrogen heterocyclic compounds have been used widely in the pharmaceutical industry, medicine and agriculture for their biological activity because of their antimicrobial, antipyretic, anti-inflammatory, and anticancer properties (Adsule et al., 2006). In this paper, we have synthesized a new Schiff base compound by the condensation of 2-(4-phenyl-3H-benzo[b][1,4]diazepin-2-yl)-phenol with diaminobenzene and characterized it by X-ray crystallography.

All the bond lengths in the compound are within normal range (Allen et al., 1987). The C9—N1 bond length is 1.289 (5) Å while C7—N2 bond length is 1.302 (5) Å that confirm they are both double bonds. Five atoms N2, C5, C7, C8 and C21 are in a plane(p1). Four atoms N1, C8, C9, C10 are in a plane(p2). The benzene ring C1—C6(p3), is approximately planar with its immediate substituent atoms C7 and O1 with a maximum deviation of 0.035 Å for O1.The benzene ring C10—C15(p4), is approximately planar with its immediate substituent atoms C9 with a maximum deviation of 0.038 Å for C9. The benzene ring C16—C21(p5). The dihedral angles formed by p1 with the p3, p4, p5 are 11.06, 80.49, 40.56°, respectively. The dihedral angles formed by p2 with the p3, p5 are 84.81, 42.56 °, respectively. The dihedral angles between p1 and p2 is 75.12 °. The molecular structure is stabilized by intramolecular O—H···N hydrogen-bonding interactions and the crystal structure is stabilized by C—H···π interactions {C13···Cg1 = 3.871, H13A···Cg1 = 3.161 Å, C13—H13A···Cg1 = 134.58° [Symmetry code: -1+x, 1/2-y, -1/2+z]; C18···Cg2 = 3.897, H18A···Cg2 = 3.126 Å, C18—H18A···Cg2 = 141.54° [Symmetry code: 1-x, -y, 1-z]; C19···Cg1 = 3.682, H19A···Cg1 = 3.169 Å, C19—H19A···Cg1 = 116.71° [Symmetry code: x, 1/2-y, 1/2+z]; C20···Cg2 = 3.685, H20A···Cg2 = 3.052 Å, C20—H20A···Cg2 = 126.85° [Symmetry code: x, 1/2-y, 1/2+z]. Cg1 and, Cg2 are the centroids of rings C1—C6, C10—C15, respectively}.

Experimental

1-(2-Hydroxy-phenyl)-ethanone (13.6 g, 0.10 mol), chlorosyl-benzene (14.1 g, 0.10 mol), potassa (0.42 g) refluxed in absolute piperidine (15 ml) result in the yellow product of 1-(2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione. The title compound was obtained by the reaction of 1-(2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione (2.04 g, 0.01 mol) and benzene-1,2-diamine (1.08 g, 0.01 mol) without solvent. Single crystals suitable for X-ray measurements were obtained by slow evaporation of an absolute ethanol at room temperature.