5-p-Tolyl-1,2,3,3a-tetra­hydro­benzo[e]pyrrolo­[2,1-b][1,3]oxazepin-10(5H)-one

Yun-Zhou Jin; Cai-E Liu; Rong-Hua Zhang; Da-Xu Fu; Yao-Kang Lv

doi:10.1107/S1600536811020964

. 2011 Jun 11;67(Pt 7):o1593. doi: 10.1107/S1600536811020964

5-p-Tolyl-1,2,3,3a-tetrahydrobenzo[e]pyrrolo[2,1-b][1,3]oxazepin-10(5H)-one

Yun-Zhou Jin ^a, Cai-E Liu ^a, Rong-Hua Zhang ^a,^*, Da-Xu Fu ^a, Yao-Kang Lv ^a

PMCID: PMC3152124 PMID: 21837001

Abstract

The structure of the title compound, C₁₉H₁₉NO₂, contains a seven-membered ring, which is fused to one five- and one six-membered ring, and carries a tolyl substituent. The two benzene rings are oriented relative to each other at a dihedral angle of 86.90 (7)°. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background to asymmetric photochemical reactions, see: Gould et al. (2001 ▶); Grätzel (2001 ▶); Korzeniewski & Zoladz (2001 ▶); Aubert et al. (2000 ▶). For related structures, see: Basarić et al. (2008 ▶); Griesbeck et al. (1997 ▶, 1999 ▶, 2002 ▶).

Experimental

Crystal data

C₁₉H₁₉NO₂
M _r = 293.35
Monoclinic,
a = 8.237 (3) Å
b = 16.868 (6) Å
c = 11.267 (4) Å
β = 100.851 (6)°
V = 1537.6 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996 ▶) T _min = 0.736, T _max = 1.000
13060 measured reflections
3501 independent reflections
2338 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.188
S = 1.01
3501 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2004 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020964/ez2247sup1.cif

e-67-o1593-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020964/ez2247Isup2.hkl

e-67-o1593-Isup2.hkl^{(171.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020964/ez2247Isup3.cml

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
C5—H5B⋯O2ⁱ	0.96	2.42	3.354 (3)	163
C17—H17A⋯O2ⁱⁱ	0.98	2.38	3.357 (3)	174

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

Acknowledgments

Financial support from the National Natural Science Foundation of China is gratefully acknowledged.

supplementary crystallographic information

Comment

Asymmetric photochemistry is one of the most important reactions in organic chemistry. Many compounds can be obtained in one step, but can not be synthesized in the ground state (Gould et al.,2001; Grätzel, 2001; Korzeniewski & Zoladz, 2001; Aubert et al., 2000). Benzophenone acylamide derivatives can form a seven-membered ring with high stereoselectivity through intramolecular photoinduced decarboxylation and cyclization (Basarić et al., 2008; Griesbeck et al., 1997; Griesbeck et al., 1999; Griesbeck et al., 2002). We report herein the crystal structure and synthesis of the title compound.

The structure of the title compound which contains a seven-membered ring, a five-membered ring and two six-membered rings is shown in Fig. 1. The dihedral angle between the two benzene rings is 86.90 (7)°. Atoms C13 and C17 of the title compound are chiral centers. There are weak C—H···O hydrogen bonds which link neighboring molecules to form a two-dimensional layer in the bc plane (Fig. 2).

Experimental

The title compound was the main product from the photoreaction of (S)-1-(2-(4-methylbenzoyl) benzoyl)pyrrolidine-2-carboxylic acid under N₂ for 10 h. The compound was purified by flash column chromatography (silica gel column, petroleum ether/ethyl acetate=3/1). Colorless crystals for the X-ray crystallographic studies were gained from slow evaporation of a dichloromethane solution.