2-Methyl-1,2,3,4-tetra­hydro­isoquinolin-6-yl N-phenyl­carbamate

Qi-Hong Zhang; Qiong Xie; Jing-Mei Wang; Zhui-Bai Qiu

doi:10.1107/S1600536809013415

. 2009 Apr 18;65(Pt 5):o1058. doi: 10.1107/S1600536809013415

2-Methyl-1,2,3,4-tetrahydroisoquinolin-6-yl N-phenylcarbamate

Qi-Hong Zhang ^a, Qiong Xie ^a, Jing-Mei Wang ^b, Zhui-Bai Qiu ^a,^*

PMCID: PMC2977739 PMID: 21583875

Abstract

In the molecule of the title compound, C₁₇H₁₈N₂O₂, the piperidine ring adopts a half-chair form. The two benzene rings are individually planar and make a dihedral angle of 53.90°. The crystal structure is stabilized by intermolecular N—H⋯N hydrogen bonds and π–π stacking interactions (centroid–centroid distance = 3.962 Å).

Related literature

For a related structure, see: (Li et al., 2006 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₂
M _r = 282.33
Monoclinic,
a = 6.0653 (6) Å
b = 15.5540 (17) Å
c = 15.1817 (16) Å
β = 93.488 (2)°
V = 1429.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.47 × 0.35 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.958, T _max = 0.963
7422 measured reflections
2662 independent reflections
2190 reflections with I > 2σ(I)
R _int = 0.087

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.128
S = 1.02
2662 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013415/rk2138sup1.cif

e-65-o1058-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013415/rk2138Isup2.hkl

e-65-o1058-Isup2.hkl^{(130.7KB, 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
N1—H1⋯N2ⁱ	0.879 (16)	2.339 (16)	3.1886 (18)	162.5 (14)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was funded in part by the National Natural Science Foundation of China (grant No. 30801435).

supplementary crystallographic information

Comment

In the molecular structure of title compound (Fig.1), the piperidine ring adopts a half–chair form, with atoms N2 and C9 out of the plane defined by the remaining four atoms. The N1—C1 bond length [1.3485 (19) Å] is longer than that (1.32 Å) for a peptide linkage. The N1—C11 bond length [1.4128 (19) Å] is shorter than a normal C—N single bond and longer than a normal C═N bond, probably as a result of electron delocalization, suggesting that the N1—C11 bond participates in the conjugated system of the benzene ring (Li et al., 2006). The two phenyl rings are planar and make a dihedral angle of 53.90°. The crystal structure is stabilized through intermolecular N1—H1···N2ⁱ hydrogen bonds [symmetry code (i): 1-x, 1-y,, 1-z] and π–π stacking interactions (Fig.2).

Experimental

The 2–methyl–1,2,3,4–tetrahydroisoquinolin–6–ol (6.13 mmol) was dissolved in anhydrous THF (100 ml), and a piece of Na metal (approximately 10 mg) was added. The mixture was stirred at room temperature for 15 min, then phenylisocyanate (18.48 mmol) was added. The reaction mixture was continuously stirred for 2 h at room temperature and monitored by TLC. The precipitate was filtered off and the filtrate was evaporated to give yellow oil. The 20 ml H₂O was added and pH of the aqueous layer was adjusted to 3 by 1 N HCl, washed with Et₂O, and then pH was adjusted to 10 by NaHCO₃aqueous solution (approximately 1%). The resulting precipitate was filtered and washed with water three times. A yellow solid (yield 1.50 g, 87%) was obtained, and single crystals suitable for crystallographic analysis were obtained by slow evaporation of an ethanol solution.