N-[4-(2-Morpholino­eth­oxy)phen­yl]acetamide monohydrate

Anuradha Gurumoorthy; Vasuki Gopalsamy; Ramamurthi K; Poonam Piplani; Ruchi Malik

doi:10.1107/S1600536810053675

. 2011 Jan 8;67(Pt 2):o262. doi: 10.1107/S1600536810053675

N-[4-(2-Morpholinoethoxy)phenyl]acetamide monohydrate

Anuradha Gurumoorthy ^a, Vasuki Gopalsamy ^b, Ramamurthi K ^c, Poonam Piplani ^d, Ruchi Malik ^d

PMCID: PMC3051513 PMID: 21522955

Abstract

In the title compound, C₁₄H₂₀N₂O₃·H₂O, the geometry about the morpholine N atom implies sp ³ hybridization. In the crystal, symmetry-related molecules are linked by intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming infinite chains along the b axis. The chain structure is further stabilized by intramolecular C—H⋯O interactions.

Related literature

For related structures, see: Ahmad et al. (2009 ▶); Fun et al. (2010 ▶); Gowda et al. (2009a ▶,b ▶); Ma et al. (2009 ▶).

Experimental

Crystal data

C₁₄H₂₀N₂O₃·H₂O
M _r = 282.34
Triclinic,
a = 7.0560 (3) Å
b = 10.2859 (6) Å
c = 10.7234 (6) Å
α = 87.572 (3)°
β = 73.326 (3)°
γ = 79.876 (3)°
V = 733.92 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.603, T _max = 0.705
17239 measured reflections
3723 independent reflections
2697 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.138
S = 1.05
3723 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ZORTEP (Zsolnai, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053675/jh2248sup1.cif

e-67-0o262-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053675/jh2248Isup2.hkl

e-67-0o262-Isup2.hkl^{(182.5KB, 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⋯O6ⁱ	0.860 (18)	2.157 (18)	3.0148 (17)	174.8 (14)
O6—H6A⋯O5	0.82 (2)	2.06 (3)	2.8640 (18)	165 (2)
O6—H6B⋯N2	0.86 (3)	2.11 (2)	2.9586 (17)	171 (2)
C4—H4⋯O1	0.93 (3)	2.32	2.890 (2)	120

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Symmetry code: (i) Inline graphic .

Acknowledgments

VG thanks the UGC, India, for financial assistance under Minor Research Project (2010–2011) and also thanks the Sophisticated Analytical Instrument Facility, IIT-Madras, Chennai, for the data collection. PP thanks the Research Fund of the University Institute of Pharmaceutical Sciences for its support to this work.

supplementary crystallographic information

Comment

Acetamide is important in the field of medicine as many biologically active compounds are synthesized by using acetamide. Benzanilides and benzamides exhibit wide range of biological activity and are extensively used in organic synthesis. Various N–substituted benzamides exhibit potent antiemetic activity (Ma et al., 2009). As a part of studying the ring and side-chain substitutions on the crystal structures of chemically and biologically important class of compounds such as acetanilides, we report herein the crystal structure of the title compound(I). The conformation of the N—H bond in the structure of the title compound(I), is anti to the C═O bond and to the phenyl ring as it has been observed in the related structures containing acetamide derivatives (Gowda et al.,2009a; Gowda et al.,2009b; Ahmad et al., 2009; Ma et al., 2009; Fun et al., 2010). Atom N1 has a trigonal configuration, the sum of three bond angles around them being 360°, whereas N2 atom is sp³ hybridized. The mean plane through the acetamide unit is inclined at a dihedral angle of 13.01 (11)° with respect to phenyl ring and 42.46 (8)° with respect to morpholine ring. The torsion angles and the least squares plane confirm that the morpholino ring is planar with the largest out-of-plane displacement of N2 (0.2458 (9) Å) and the phenyl ring is also planar with the root mean square deviation of 0.0034 Å.The morpholinoethoxy substitution at C6 [C4—C5—C6—O3=179.86 (13)°] is in anti-periplanar position. The exocyclic angle C2—N1—C3 [128.45 (11)°] deviates significantly from the normal value of 120°. This may be due to the intramolecular non-bonded interactions between atom O1 and H4 at C4 (O1······.H4 = 2.3159 Å). The widening of the exocyclic angle C5—C6—O3 [125.00 (12)°] deviate significantly from the normal value of 120° might be due to the consequence of repulsion between H5 and H9B at C9 (H5···H9B=2.3233 Å). The exocyclic angle O3—C9—C10 [103.45 (11)°] deviates by ca 6° from the tetrahedral value because of the intramolecular non-bonded interaction between O3 and H10A at C10 (O3···H10A = 2.3848 Å). The widening of the exocyclic angle C9—C10—N2[113.88 (11)°] from the normal value of 109° may be due to the repulsion between H9B and H11A [H9B···H11A = 2.3257 Å]. In the crystal structure, symmetry related molecules are linked by linear intermolecular N—H···O, O—H···O and O—H···N hydrogen bonds to form an infinite one-dimensional chain along the b axis.

Experimental

N-[4-Hydroxyphenyl]acetamide (1.0 g, 6.62 mmol) was dissolved in ethyl methyl ketone (100 ml) and anhydrous potassium carbonate (3.0–4.0 g) was added. The reaction mixture was refluxed for 2 hrs. To it 4-(2-chloroethyl) morpholine hydrochloride (1.0 g, 6.68 mmol) was added and the reaction mixture was further refluxed with continuous stirring for 7 h. Reaction was monitored with the help of TLC. The slurry obtained was filtered, the solvent was removed under reduced pressure and the solid obtained was crystallized from a mixture of ethyl acetate and ether to afford the title compound(I) (1.43 g, 81.81%), mp 100–102°C.