N-[Morpholino(phen­yl)meth­yl]benzamide

L Muruganandam; S Rajeswari; D Tamilvendan; V Ramkumar; G Venkatesa Prabhu

doi:10.1107/S1600536809005327

. 2009 Feb 21;65(Pt 3):o578. doi: 10.1107/S1600536809005327

N-[Morpholino(phenyl)methyl]benzamide

L Muruganandam ^a, S Rajeswari ^a, D Tamilvendan ^a, V Ramkumar ^b, G Venkatesa Prabhu ^a,^*

PMCID: PMC2968586 PMID: 21582233

Abstract

The title compound, C₁₈H₂₀N₂O₂, crystallizes with two molecules in the asymmetric unit. The morpholine rings of both molecules adopt chair conformations. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds. One phenyl ring is disordered over two orientations in a 0.665 (5):0.335 (5) ratio.

Related literature

For background literature on benzamides and morpholines, see: Carbonnelle et al. (2005 ▶); Hatzelmann & Schudt (2001 ▶); Li et al. (1998 ▶); Malik et al. (2006 ▶); Sedavkina et al. (1984 ▶); Simonini et al. (2006 ▶); Suzuki et al. (2005 ▶); Zhou et al. (1999); Zhou et al. (1999 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₈H₂₀N₂O₂
M _r = 296.36
Triclinic,
a = 9.9190 (3) Å
b = 10.6793 (3) Å
c = 15.8050 (5) Å
α = 79.747 (2)°
β = 85.543 (1)°
γ = 85.467 (1)°
V = 1638.84 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.20 × 0.19 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.979, T _max = 0.994
21213 measured reflections
7329 independent reflections
4069 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.156
S = 1.03
7329 reflections
417 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005327/hb2906sup1.cif

e-65-0o578-sup1.cif^{(30.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005327/hb2906Isup2.hkl

e-65-0o578-Isup2.hkl^{(351.3KB, 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
N4—H4⋯O2	0.85 (2)	2.11 (2)	2.932 (2)	163.5 (17)
N2—H2⋯O4ⁱ	0.832 (19)	2.10 (2)	2.918 (2)	166.5 (17)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Department of Chemistry, IITMadras, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Benzamide derivatives, known for their anti-inflammatory and immunomodulatory (Hatezelmann et al., 2001; Carbonnelle et al., 2005), anti-tumoral (Suzuki et al., 2005), antipsychotic (Simonini et al., 2006), and antiallergic (Zhou et al.,1999) activities, are drugs widely used in medicine (Malik et al., 2006).

Morpholine is a multipurpose chemical which is used as a solvent for resins, dyes and waxes. One of its most important use is as a chemical intermediate in the preparation of pesticides (Li et al., 1998). A number of morpholine derivatives have been described as analgesics and local anesthetics. The morpholinomethyl derivative of pyrizinamide (morphozinamide) has been found to be more effective in the treatment of tuberculosis than pyrizinamide (Sedavkina et al., 1984).

In the title compound, (I), each of the two independent molecules contains three ring systems, one phenyl ring, one benzamide and a morpholino ring (Fig. 1).

The morpholine rings of the two molecules adopts the usual chair conformation (Q_T = 0.577 (2) Å, q(2)=0.012 (2)Å and q(3)=0.577 (2) Å, θ = 1.4 (2)°. (Cremer & Pople, 1975). The best planes of the rings pass through the C atoms, leaving the O and N atoms on either side. The methine (C—H) substitution (C5) of the morpholine ring is in an equatorial position. One of the benzamide moiety in the crystal structure is disordered with an occupancy factor of 0.33 and 0.67. The phenyl moiety is planar. The crystal structure is stabilized by intermolecular N—H···O hydrogen bonds (Table 1).

Experimental

Benzamide (12.1 g, 0.1 mol) was dissolved in a minimum quantity of ethanol. To this solution, benzaldehdye (10 ml, 0.1 mol) followed by morpholine (9 ml, 0.1 mol) was added in small quantities with constant stirring in an ice bath. For about 2 hrs, the mixture was kept at ice cold temperature. After 10 days a pale yellow semi-solid was obtained. The product was purified by washing with distilled water several times and finally with 5 ml of acetone. The compound was dried in an air oven at 80° C and recrystallized from ethanol to yield colourless slabs of (I).