2. Experimental Crystal data
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1 data reports ISSN 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 and B. Gunasekaran d * a Department of Chemistry, National College, Tiruchirappalli , Tamil Nadu, India, b PG and Research Dept of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli, Tamil Nadu , India, c Sri Arumugam Group of Institutions, Tholudhur, Tamil Nadu, India, and d Department of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai Tamil Nadu, India. *Correspondence phdguna@gmail.com 2. Experimental 2.1. Crystal data C 16 H 18 N 2 O 2 S M r = Monoclinic, P2 1 =c a = (11) Å b = (7) Å c = (5) Å = (2) V = (17) Å 3 Z =4 Mo K radiation = 0.21 mm 1 T = 295 K mm Received 14 June 2015; accepted 16 June 2015 Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland In the title compound, C 16 H 18 N 2 O 2 S, the morpholine ring adopts a chair conformation. The thiophene ring makes a dihedral angle of (14) with the mean plane of the four C atoms [maximum deviation = (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 (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 HO hydrogen bonds, forming chains along [001]. Keywords: crystal structure; benzamide; morpholino; thiophene; hydrogen bonding. CCDC reference: 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) Data collection Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.920, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 227 parameters Table 1 Hydrogen-bond geometry (Å, ) measured reflections 3836 independent reflections 2744 reflections with I > 2(I) R int = restraint H-atom parameters constrained max = 0.62 e Å 3 min = 0.41 e Å 3 D HA D H HA DA D HA N1 H1O1 i (2) 173 Symmetry code: (i) x; y þ 1 2 ; z 1 2. 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. Supporting information for this paper is available from the IUCr electronic archives (Reference: SU5156). o498 Prabhu et al. doi: /s
2 data reports References Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Carbonnelle, D., Ebstein, F., Rabu, C., Petit, J. Y., Gregoire, M. & Lang, F. (2005). Eur. J. Immunol. 35, Hatzelmann, A. & Schudt, C. (2001). J. Pharmacol. Exp. Ther. 297, Khan, M. R., Khan, A., Tahir, M. N., Adeel, M. & Ahmad, S. (2012). Acta Cryst. E68, o653. Muruganandam, L., Rajeswari, S., Tamilvendan, D., Ramkumar, V. & Prabhu, G. V. (2009). Acta Cryst. E65, o578. Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, Simonini, M. V., Camargo, L. M., Dong, E., Maloku, E., Veldic, M., Costa, E. & Guidotti, A. (2006). Proc. Natl Acad. Sci. USA, 103, Spek, A. L. (2009). Acta Cryst. D65, Suzuki, K., Nagasawa, H., Uto, Y., Sugimoto, Y., Noguchi, K., Wakida, M., Wierzba, K., Terada, T., Asao, T., Yamada, Y., Kitazato, K. & Hori, H. (2005). Bioorg. Med. Chem. 13, Zhou, Y., Xu, L., Wu, Y. & Liu, B. (1999). Chemom. Intell. Lab. Syst. 45, Prabhu et al. C 16 H 18 N 2 O 2 S o499
3 supporting information [doi: /s ] Crystal structure of N-[(morpholin-4-yl)(thiophen-2-yl)methyl]benzamide S. Arun Prabhu, M. Suresh, A. Abdul Jameel, M. Syed Ali Padusha and B. Gunasekaran 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 (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 = 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), antitumoral (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 (14) with the mean plane of the four C atoms (maximum deviation (3) Å) of the morpholine ring. The benzamide ring is disordered with four C atoms occupying two positions, with a refined occupancy ratio of (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 sup-1
4 Figure 1 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. sup-2
5 Figure 2 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. N-[(Morpholin-4-yl)(thiophen-2-yl)methyl]benzamide Crystal data C 16 H 18 N 2 O 2 S M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc a = (11) Å b = (7) Å c = (5) Å β = (2) V = (17) Å 3 Z = 4 Data collection Bruker APEXII CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator Detector resolution: 0 pixels mm -1 ω and φ scans F(000) = 640 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 3836 reflections θ = µ = 0.21 mm 1 T = 295 K Block, colourless mm Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.920, T max = measured reflections 3836 independent reflections 2744 reflections with I > 2σ(I) sup-3
6 R int = θ max = 28.3, θ min = 2.4 h = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 227 parameters 1 restraint Primary atom site location: structure-invariant direct methods k = l = 12 7 Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.097P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.62 e Å 3 Δρ min = 0.41 e Å 3 Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Occ. (<1) S (4) (7) (8) (3) N (10) (16) (16) (4) O (12) (16) (2) (5) O (11) (3) (16) (7) N (10) (18) (16) (4) H * C (13) (2) (2) (5) H * C (12) (2) (2) (5) C (13) (2) (2) (5) C (4) (8) (8) (2) (4) H * (4) C (3) (7) (6) (16) (4) H * (4) C2A (3) (7) (7) (18) (4) H2A * (4) C6A (4) (9) (8) (3) (4) H6A * (4) C (15) (2) (3) (5) H * C (11) (19) (2) (4) C (11) (2) (19) (4) H * C (15) (2) (3) (6) H * C (14) (2) (2) (5) H9A * H9B * C (17) (2) (3) (6) H10A * H10B * sup-4
7 C (14) (2) (2) (5) H12A * H12B * C (16) (2) (3) (6) H11A * H11B * C (2) (6) (5) (16) H * C (4) (11) (11) (3) (4) H * (4) C (4) (11) (8) (3) (4) H * (4) C3A (4) (10) (8) (3) (4) H3A * (4) C5A (4) (13) (11) (3) (4) H5A * (4) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 S (3) (4) (6) (2) (3) (3) N (8) (8) (8) (6) (6) (6) O (12) (9) (11) (8) (9) (7) O (10) (2) (8) (11) (7) (9) N (8) (10) (7) (7) (6) (7) C (10) (11) (9) (8) (8) (8) C (10) (12) (9) (8) (7) (8) C (10) (14) (10) (9) (8) (10) C (3) (6) (5) (3) (3) (4) C (2) (4) (3) (2) (2) (3) C2A (3) (4) (4) (3) (3) (3) C6A (3) (7) (5) (4) (3) (5) C (12) (11) (13) (9) (11) (10) C (9) (10) (9) (7) (7) (7) C (8) (10) (8) (7) (7) (7) C (12) (13) (18) (10) (11) (12) C (12) (11) (10) (9) (9) (8) C (16) (13) (12) (11) (11) (10) C (11) (12) (12) (9) (9) (9) C (14) (12) (16) (10) (12) (11) C (15) (5) (3) (2) (17) (3) C (4) (9) (8) (5) (4) (6) C (3) (9) (5) (4) (3) (5) C3A (4) (7) (5) (5) (4) (5) C5A (3) (10) (7) (5) (4) (7) sup-5
8 Geometric parameters (Å, º) S1 C (2) C6A H6A S1 C (19) C15 C (3) N2 C (2) C15 H N2 C (2) C13 C (3) N2 C (2) C8 H O2 C (3) C16 H O2 C (3) C9 C (3) O1 C (3) C9 H9A N1 C (3) C9 H9B N1 C (2) C10 H10A N1 H C10 H10B C14 C (3) C12 C (3) C14 C (3) C12 H12A C14 H C12 H12B C7 C (3) C11 H11A C1 C (6) C11 H11B C1 C (6) C4 C5A (11) C1 C2A (7) C4 C (11) C1 C6A (7) C4 C (10) C2 C (9) C4 C3A (11) C2 H C4 H C6 C (7) C3 H C6 H C5 H C2A C3A (8) C3A H3A C2A H2A C5A H5A C6A C5A (10) C16 S1 C (11) C15 C16 H C8 N2 C (15) S1 C16 H C8 N2 C (15) N2 C9 C (17) C12 N2 C (16) N2 C9 H9A C11 O2 C (18) C10 C9 H9A C7 N1 C (15) N2 C9 H9B C7 N1 H C10 C9 H9B C8 N1 H H9A C9 H9B C13 C14 C (19) O2 C10 C (2) C13 C14 H O2 C10 H10A C15 C14 H C9 C10 H10A O1 C7 N (19) O2 C10 H10B O1 C7 C (19) C9 C10 H10B N1 C7 C (17) H10A C10 H10B C6 C1 C (4) N2 C12 C (18) C6 C1 C2A 78.9 (4) N2 C12 H12A C2 C1 C2A 72.9 (5) C11 C12 H12A C6 C1 C6A 72.0 (4) N2 C12 H12B C2 C1 C6A 77.6 (5) C11 C12 H12B sup-6
9 C2A C1 C6A (4) H12A C12 H12B C6 C1 C (3) O2 C11 C (19) C2 C1 C (3) O2 C11 H11A C2A C1 C (3) C12 C11 H11A C6A C1 C (4) O2 C11 H11B C1 C2 C (7) C12 C11 H11B C1 C2 H H11A C11 H11B C3 C2 H C5A C4 C (7) C1 C6 C (6) C5A C4 C (7) C1 C6 H C3 C4 C (5) C5 C6 H C5A C4 C3A (5) C1 C2A C3A (6) C3 C4 C3A 72.4 (6) C1 C2A H2A C5 C4 C3A 80.2 (5) C3A C2A H2A C5A C4 H C5A C6A C (7) C3 C4 H C5A C6A H6A C5 C4 H C1 C6A H6A C3A C4 H C16 C15 C (2) C4 C3 C (7) C16 C15 H C4 C3 H C14 C15 H C2 C3 H C14 C13 C (17) C6 C5 C (6) C14 C13 S (15) C6 C5 H C8 C13 S (14) C4 C5 H N2 C8 N (15) C2A C3A C (7) N2 C8 C (14) C2A C3A H3A N1 C8 C (16) C4 C3A H3A N2 C8 H C4 C5A C6A (8) N1 C8 H C4 C5A H5A C13 C8 H C6A C5A H5A C15 C16 S (18) C8 N1 C7 O1 2.6 (3) C9 N2 C8 C (2) C8 N1 C7 C (18) C7 N1 C8 N (2) O1 C7 C1 C (4) C7 N1 C8 C (2) N1 C7 C1 C (4) C14 C13 C8 N (2) O1 C7 C1 C (5) S1 C13 C8 N (2) N1 C7 C1 C (5) C14 C13 C8 N1 2.7 (3) O1 C7 C1 C2A (4) S1 C13 C8 N (13) N1 C7 C1 C2A 48.5 (4) C14 C15 C16 S1 0.7 (3) O1 C7 C1 C6A 44.8 (5) C13 S1 C16 C (2) N1 C7 C1 C6A (5) C8 N2 C9 C (17) C6 C1 C2 C3 2.8 (10) C12 N2 C9 C (2) C2A C1 C2 C (8) C11 O2 C10 C (3) C6A C1 C2 C (8) N2 C9 C10 O (3) C7 C1 C2 C (6) C8 N2 C12 C (17) C2 C1 C6 C5 5.1 (9) C9 N2 C12 C (2) C2A C1 C6 C (7) C10 O2 C11 C (3) C6A C1 C6 C (7) N2 C12 C11 O (2) sup-7
10 C7 C1 C6 C (5) C5A C4 C3 C (10) C6 C1 C2A C3A 64.4 (7) C5 C4 C3 C2 2.7 (14) C2 C1 C2A C3A 65.0 (7) C3A C4 C3 C (10) C6A C1 C2A C3A 1.1 (9) C1 C2 C3 C4 1.6 (14) C7 C1 C2A C3A (5) C1 C6 C5 C4 6.3 (11) C6 C1 C6A C5A 66.7 (8) C5A C4 C5 C (9) C2 C1 C6A C5A 63.9 (9) C3 C4 C5 C6 5.1 (12) C2A C1 C6A C5A 0.4 (10) C3A C4 C5 C (8) C7 C1 C6A C5A (7) C1 C2A C3A C4 1.0 (10) C13 C14 C15 C (3) C5A C4 C3A C2A 1.0 (11) C15 C14 C13 C (19) C3 C4 C3A C2A 63.8 (7) C15 C14 C13 S1 1.8 (2) C5 C4 C3A C2A 58.7 (7) C16 S1 C13 C (17) C3 C4 C5A C6A 58.5 (9) C16 S1 C13 C (17) C5 C4 C5A C6A 65.1 (9) C12 N2 C8 N (2) C3A C4 C5A C6A 2.6 (14) C9 N2 C8 N (2) C1 C6A C5A C4 2.3 (14) C12 N2 C8 C (15) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A N1 H1 O1 i (2) 173 Symmetry code: (i) x, y+1/2, z 1/2. sup-8
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