Crystal structure of N-[(morpholin-4-yl)(thio­phen-2-yl)meth­yl]benzamide

S Arun Prabhu; M Suresh; A Abdul Jameel; M Syed Ali Padusha; B Gunasekaran

doi:10.1107/S2056989015011639

. 2015 Jun 20;71(Pt 7):o498–o499. doi: 10.1107/S2056989015011639

Crystal structure of N-[(morpholin-4-yl)(thiophen-2-yl)methyl]benzamide

S Arun Prabhu ^a, M Suresh ^b, A Abdul Jameel ^c, M Syed Ali Padusha ^b, B Gunasekaran ^d,^*

PMCID: PMC4518906 PMID: 26279929

Abstract

In the title compound, C₁₆H₁₈N₂O₂S, the morpholine ring adopts a chair conformation. The thiophene ring makes a dihedral angle of 63.54 (14)° with the mean plane of the four C atoms [maximum deviation = 0.010 (3) Å] of the morpholine ring. The benzamide ring is disordered, with four C atoms occupying two sets of sites, with a refined occupancy ratio of 0.502 (4):0.498 (4). These two rings are inclined to one another by 85.2 (4)° and to the thiophene ring by 72.7 (3) and 13.0 (3)° for the major and minor components, respectively. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming chains along [001].

Keywords: crystal structure, benzamide, morpholino, thiophene, hydrogen bonding

Related literature

For the biological activity of benzamide derivatives, see: Carbonnelle et al. (2005 ▸); Hatzelmann & Schudt (2001 ▸); Simonini et al. (2006 ▸); Suzuki et al. (2005 ▸); Zhou et al. (1999 ▸); For related structures see: Muruganandam et al. (2009 ▸); Khan et al. (2012 ▸). graphic file with name e-71-0o498-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₈N₂O₂S
M _r = 302.38
Monoclinic,
a = 16.5283 (11) Å
b = 9.9049 (7) Å
c = 9.6831 (5) Å
β = 99.056 (2)°
V = 1565.47 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T _min = 0.920, T _max = 0.959
11905 measured reflections
3836 independent reflections
2744 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.182
S = 1.04
3836 reflections
227 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); 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 ▸); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015011639/su5156sup1.cif

e-71-0o498-sup1.cif^{(27.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011639/su5156Isup2.hkl

e-71-0o498-Isup2.hkl^{(184.2KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015011639/su5156Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015011639/su5156fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The minor component of the disordered benzamide ring is shown with dashed lines.

Click here for additional data file.^{(1.6MB, tif)}

b . DOI: 10.1107/S2056989015011639/su5156fig2.tif

A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details). The C-bound H atoms and the minor component of the disordered benzamide ring have been omitted for clarity.

CCDC reference: 1406913

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1O1ⁱ	0.86	2.02	2.878(2)	173

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

S1. Synthesis and crystallization

To an alkaline solution of benzamide (0.025 mol, 3.03 g), morpholine (0.025 mol, 2.2 ml) was added drop wise in ice cold conditions and the contents were stirred for 5 min. Thiophene-2-aldehyde (0.025 mol, 2.3 ml) was then added drop wise and stirring was continued for 1 h. The Mannich base product formed was filtered, washed with water and recrystallized with ethanol (yield: 75%; m.p.: 433 K) giving colourless block-like crystals.

S2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Four C atoms in the benzamide ring (C2/C2A, C3/C3A, C5/C5A, and C6/C6A) are disordered over two positions with a refined occupany ratio of 0.502 (5):0.48 (5). All of the H atoms were positioned geometrically and refined using a riding model: N—H = 0.86 Å, C—H = 0.93 - 0.98 Å with U_iso(H) = 1.2U_eq(N,C).

S3. Comment

Benzamide and its derivatives, have recently received great attention because of their wide range of pharmacological activities, such as anti-inflammatory, immunomodulatory (Hatzelmann & Schudt, 2001; Carbonnelle et al., 2005), anti-tumoral (Suzuki et al., 2005), antipsychotic (Simonini et al., 2006), and antiallergic (Zhou et al., 1999).

The geometric parameters of the title compound (Fig. 1) agree well with those reported for similar structures (Muruganandam et al., 2009; Khan et al., 2012). The morpholine ring adopts a chair conformation. The thiophene ring makes a dihedral angle of 63.54 (14) ° with the mean plane of the four C atoms (maximum deviation 0.010 (3) Å) of the morpholine ring. The benzamide ring is disordered with four C atoms occupying two positions, with a refined occupancy ratio of 0.502 (5):0.498 (5). These two rings are inclined to one another by 85.2 (4) ° and to the thiophene ring by 72.7 (3) and 13.0 (3) °, for the major and minor component, respectively.

In the crystal, molecules are linked via N—H···O hydrogen bonds forming chains along [001]; see Table 1 and Fig. 2