N-p-Tolyladamantane-1-carboxamide

Weiwei SiMa

doi:10.1107/S1600536809036101

. 2009 Sep 12;65(Pt 10):o2452. doi: 10.1107/S1600536809036101

N-p-Tolyladamantane-1-carboxamide

Weiwei SiMa ^a,^*

PMCID: PMC2970359 PMID: 21577907

Abstract

In the crystal of the title compound, C₁₈H₂₃NO, the molecules are linked into chains along the c axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For For bond-length data, see: Allen et al. (1987 ▶). For the synthesis of the title compound, see: Karle et al. (1997 ▶); Tadashi et al. (1969 ▶)

Experimental

Crystal data

C₁₈H₂₃NO
M _r = 269.37
Orthorhombic,
a = 30.708 (7) Å
b = 9.7927 (2) Å
c = 10.0203 (6) Å
V = 3013.2 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.50 × 0.30 × 0.30 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.964, T _max = 0.978
27405 measured reflections
3443 independent reflections
2652 reflections with I > 2σ(I)
R _int = 0.080

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.174
S = 1.16
3443 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036101/er2072sup1.cif

e-65-o2452-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036101/er2072Isup2.hkl

e-65-o2452-Isup2.hkl^{(169KB, 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⋯O1ⁱ	0.86	2.12	2.962 (2)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

Comment

The unique structure of adamantane and the pharmaccutical effects of adamantane-containing agents on virus (Davis et al., 1964) have attracted many chemists and pharmacologists to do considerable work on the syntheses of adamantane derivatives (Fort et al., 1964). The crystal structure of the title compound (I) is reported herein.

The molecular structure of compound (I), C₁₈H₂₃ON, is shown in Figure 1. All bond lengths and bond correspond to the geometry parameters expected for atom types and the type of hybridization (Allen et al., 1987). The bonds to nitrogen of the title amide, Fig. 1, the torsion angles of O1—C8—N1—C1 and C9—C8—N1—C1 are 1.70 (3)° and 178.59 (18)°, respectively. The C8—N1 bond has considerable double-bond characer, at 1.349 (2) Å, is substantially shorter than the normal C—N single-bond distance observed in amines. In the crystal of (I), the intermolecular N₁—H···O₁ H-bonds linked molecules to chains along the c axis (Fig.2). And the N₁—H···O₁ bond length is 2.962 (2) Å.

Experimental

A solution of freshly prepared 1-adamantane carbonyl chloride (1 mmol, prepared by refluxing 1-adamantane carboxylic acid with 3M excess of SOCl₂) in dry CH₂Cl₂ was added dropwise to a well stirred and ice-cooled solution of p-toluidine (1 mmol) and triethylamine (2 mmol) in the same solvent. After 24 h of stirring at room temperature, the solvents were removed in vacuo and the residue was recrystallized from methanol. Colorless single crystals of the title compound suitable for X-ray diffraction analysis were obtained then and the yield was 80% (Isabella et al. 1997; Tadashi et al., 1969).