N-[(Methylsulfanyl)methyl]benzamide

Azim Khan

N-[(Methylsulfanyl)methyl]benzamide

Azim Khan

2012, Acta Crystallographica Section E Structure Reports Online

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organic compounds Acta Crystallographica Section E Data collection Structure Reports Online 9379 measured reflections 2371 independent reflections 1722 reflections with I > 2(I) Rint = 0.022 Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.932, Tmax = 0.950 ISSN 1600-5368 N-[(Methylsulfanyl)methyl]benzamide Refinement Muhammad Riaz Khan,a Azim Khan,a M. Nawaz Tahir,b* Muhammad Adeela and Saeed Ahmada R[F 2 > 2(F 2)] = 0.041 wR(F 2) = 0.116 S = 1.07 2371 reflections 110 parameters H-atom parameters constrained max = 0.18 e Å3 min = 0.26 e Å3 a Department of Chemistry, Gomal University, Dera Ismail Khan, K.P.K., Pakistan, and bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan Correspondence e-mail: [email protected] Received 1 February 2012; accepted 2 February 2012 Table 1 Hydrogen-bond geometry (Å, ). D—H A Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.002 Å; R factor = 0.041; wR factor = 0.116; data-to-parameter ratio = 21.6. i N1—H1 O1 C8—H8B O1ii D—H H A D A D—H A 0.86 0.97 2.02 2.53 2.8438 (17) 3.434 (2) 160 154 Symmetry codes: (i) x þ 12; y þ 12; z; (ii) x þ 12; y þ 12; z. In the title compound, C9H11NOS, the phenyl ring and formamide unit make a dihedral angle of 23.93 (14) , whereas the (methylsulfanyl)methyl group is oriented at a dihedral angle of 61.31 (8) with respect to the phenyl ring. There are intermolecular N—H O hydrogen bonds, forming C(4) chains along the [010] direction. These polymeric chains are linked by C—H O hydrogen bonds to form polymeric sheets in the (110) plane. Related literature For crystal structures containing the 1-(methylsulfanyl)methanamine grouping, see: Siddiqui et al. (2008); Noroozi Pesyan et al. (2009). For graph-set notation, see: Bernstein et al. (1995). Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON. The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2467). References Experimental Crystal data C9H11NOS Mr = 181.25 Orthorhombic, Pbca a = 9.7841 (4) Å b = 9.2116 (4) Å c = 21.2663 (8) Å Acta Cryst. (2012). E68, o653 V = 1916.67 (14) Å3 Z=8 Mo K radiation = 0.29 mm1 T = 296 K 0.26 0.20 0.18 mm Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Noroozi Pesyan, N., Omidkhah, N., Maghsoodi, M. & Patrick, B. O. (2009). Acta Cryst. E65, o655. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Siddiqui, W. A., Ahmad, S., Siddiqui, H. L., Hussain, R. A. & Parvez, M. (2008). Acta Cryst. E64, o1897. Spek, A. L. (2009). Acta Cryst. D65, 148–155. doi:10.1107/S1600536812004515 Khan et al. o653 supporting information supporting information Acta Cryst. (2012). E68, o653 [doi:10.1107/S1600536812004515] N-[(Methylsulfanyl)methyl]benzamide Muhammad Riaz Khan, Azim Khan, M. Nawaz Tahir, Muhammad Adeel and Saeed Ahmad S1. Comment The title compound (Fig. 1) was prepared in an attempt to synthesize a different compound from benzamide and phthalic anhydride in dimethyl sulphoxide. The crystal structures of 2-((methylsulfanyl)methyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Siddiqui et al., 2008) and 5-(2,6-dimethoxyphenoxy)-2-methylsulfanylmethyl-2H-tetrazole (Noroozi Pesyan et al., 2009) have been published; these contain the 1-(methylsulfanyl)methanamine grouping. Let A, B, C denote the planes defined by the phenyl ring (C1–C6), the formamide unit (O1/C7/N1) and the (methylsulfanyl)methane grouping (C8/S1/C9), respectively. The dihedral angles between A/B, A/C and B/C are 23.93 (14)°, 61.31 (8)° and 67.92 (13)°, respectively. There are intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2), forming C(4) chains (Bernstein et al., 1995) along the [010] direction. These polymeric chains are linked by C—H···O hydrogen bonds (Table 1, Fig. 2) to form polymeric sheets in the (110) plane. S2. Experimental The title compound was prepared by adding a solution of benzamide (0.1 g, 0.078 mmol) in 3 ml of dimethyl sulphoxide (DMSO) to a solution of phthalic anhydride (0.1 g, 0.078 mmol) in DMSO (3 ml). The reaction mixture was heated to 353 K for 6 h. The organic and aqueous layers were separated and the latter was extracted with chloroform (3×15 ml). The organic layer was concentrated in vacuo and the residue was purified by chromatography (silica gel, EtOAc/hexane= 1:4). The title compound was obtained as a colorless crystalline solid. Yield = 0.14 g, 70%, m.p = 365 K. Crystallization from a saturated chloroform solution at ambient temperature gave colourless prisms. S3. Refinement The H-atoms were positioned geometrically (N—H = 0.86 Å, C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl groups and x = 1.2 for all other H-atoms. Acta Cryst. (2012). E68, o653 sup-1 supporting information Figure 1 View of the title compound, with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown as small circles of arbitrary radius. Acta Cryst. (2012). E68, o653 sup-2 supporting information Figure 2 Packing diagram of the title compound (PLATON: Spek, 2009) showing that molecules form one dimensional polymeric chains along [010] and are interlinked. H atoms not involved in hydrogen bonding have been omitted for clarity. N-[(methylsulfanyl)methyl]benzamide Crystal data C9H11NOS Mr = 181.25 Orthorhombic, Pbca Hall symbol: -P 2ac 2ab a = 9.7841 (4) Å b = 9.2116 (4) Å c = 21.2663 (8) Å V = 1916.67 (14) Å3 Z=8 Acta Cryst. (2012). E68, o653 F(000) = 768 Dx = 1.256 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1722 reflections θ = 1.9–28.3° µ = 0.29 mm−1 T = 296 K Prism, colorless 0.26 × 0.20 × 0.18 mm sup-3 supporting information Data collection Bruker Kappa APEXII CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator Detector resolution: 7.50 pixels mm-1 ω scans Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.932, Tmax = 0.950 9379 measured reflections 2371 independent reflections 1722 reflections with I > 2σ(I) Rint = 0.022 θmax = 28.3°, θmin = 1.9° h = −12→12 k = −12→12 l = −27→28 Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.041 wR(F2) = 0.116 S = 1.07 2371 reflections 110 parameters 0 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0531P)2 + 0.2845P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 0.18 e Å−3 Δρmin = −0.26 e Å−3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) S1 O1 N1 C1 C2 C3 C4 C5 C6 C7 C8 C9 H1 H2 H3 H4 H5 x y z Uiso*/Ueq 0.20155 (6) 0.14747 (12) 0.25653 (14) 0.15800 (14) 0.04865 (18) 0.0203 (2) 0.1003 (2) 0.2082 (2) 0.23778 (18) 0.18659 (14) 0.29981 (18) 0.0467 (2) 0.27659 −0.00569 −0.05341 0.08116 0.26188 0.43391 (6) 0.17375 (11) 0.38548 (15) 0.34302 (14) 0.28086 (18) 0.3207 (2) 0.4214 (2) 0.4838 (2) 0.44502 (17) 0.29393 (15) 0.3490 (2) 0.3318 (3) 0.46996 0.21226 0.27902 0.44708 0.55253 −0.09248 (2) 0.05060 (5) 0.03218 (5) 0.13470 (7) 0.16623 (8) 0.22745 (9) 0.25775 (9) 0.22691 (8) 0.16551 (7) 0.06896 (7) −0.03071 (7) −0.08796 (11) 0.04670 0.14612 0.24832 0.29912 0.24731 0.0717 (2) 0.0537 (4) 0.0493 (4) 0.0427 (4) 0.0562 (5) 0.0710 (7) 0.0709 (7) 0.0648 (6) 0.0525 (5) 0.0424 (4) 0.0559 (6) 0.0905 (9) 0.0592* 0.0674* 0.0852* 0.0851* 0.0778* Acta Cryst. (2012). E68, o653 sup-4 supporting information H6 H8A H8B H9A H9B H9C 0.31140 0.29434 0.39487 0.00311 0.06706 −0.01321 0.48753 0.24449 0.37666 0.34980 0.23019 0.36045 0.14487 −0.03582 −0.03557 −0.04829 −0.09169 −0.12147 0.0630* 0.0670* 0.0670* 0.1358* 0.1358* 0.1358* Atomic displacement parameters (Å2) S1 O1 N1 C1 C2 C3 C4 C5 C6 C7 C8 C9 U11 U22 U33 U12 U13 U23 0.0957 (4) 0.0662 (7) 0.0605 (8) 0.0465 (8) 0.0588 (10) 0.0765 (13) 0.0883 (14) 0.0733 (12) 0.0541 (9) 0.0445 (8) 0.0568 (10) 0.0826 (15) 0.0699 (4) 0.0395 (6) 0.0426 (7) 0.0375 (7) 0.0498 (9) 0.0686 (11) 0.0736 (12) 0.0685 (11) 0.0566 (9) 0.0372 (7) 0.0632 (10) 0.0997 (17) 0.0496 (3) 0.0553 (6) 0.0448 (7) 0.0440 (7) 0.0600 (9) 0.0679 (12) 0.0509 (10) 0.0526 (10) 0.0468 (8) 0.0454 (8) 0.0476 (9) 0.0893 (15) −0.0010 (3) −0.0005 (5) −0.0021 (6) 0.0072 (6) −0.0024 (7) −0.0042 (10) 0.0057 (11) −0.0033 (9) −0.0028 (7) 0.0059 (6) 0.0011 (8) 0.0017 (13) −0.0003 (2) −0.0022 (5) 0.0027 (6) −0.0033 (6) 0.0056 (8) 0.0239 (9) 0.0117 (9) −0.0067 (8) −0.0045 (7) −0.0057 (6) 0.0064 (7) −0.0291 (12) 0.0110 (2) −0.0059 (5) −0.0046 (5) 0.0001 (6) −0.0074 (7) −0.0067 (9) −0.0129 (9) −0.0134 (9) −0.0024 (7) −0.0001 (6) −0.0031 (8) 0.0092 (12) Geometric parameters (Å, º) S1—C8 S1—C9 O1—C7 N1—C7 N1—C8 N1—H1 C1—C6 C1—C7 C1—C2 C2—C3 C3—C4 C4—C5 1.8060 (17) 1.786 (2) 1.2347 (17) 1.3384 (19) 1.4426 (19) 0.8600 1.386 (2) 1.496 (2) 1.386 (2) 1.381 (3) 1.374 (3) 1.369 (3) C5—C6 C2—H2 C3—H3 C4—H4 C5—H5 C6—H6 C8—H8A C8—H8B C9—H9A C9—H9B C9—H9C 1.384 (2) 0.9300 0.9300 0.9300 0.9300 0.9300 0.9700 0.9700 0.9600 0.9600 0.9600 C8—S1—C9 C7—N1—C8 C8—N1—H1 C7—N1—H1 C2—C1—C7 C2—C1—C6 C6—C1—C7 C1—C2—C3 C2—C3—C4 C3—C4—C5 100.62 (10) 123.03 (14) 118.00 118.00 118.13 (13) 119.07 (14) 122.78 (13) 120.08 (16) 120.47 (18) 119.86 (18) C4—C3—H3 C3—C4—H4 C5—C4—H4 C4—C5—H5 C6—C5—H5 C1—C6—H6 C5—C6—H6 S1—C8—H8A S1—C8—H8B N1—C8—H8A 120.00 120.00 120.00 120.00 120.00 120.00 120.00 109.00 109.00 109.00 Acta Cryst. (2012). E68, o653 sup-5 supporting information C4—C5—C6 C1—C6—C5 O1—C7—N1 O1—C7—C1 N1—C7—C1 S1—C8—N1 C1—C2—H2 C3—C2—H2 C2—C3—H3 120.31 (17) 120.20 (16) 122.59 (14) 120.58 (13) 116.83 (12) 114.66 (12) 120.00 120.00 120.00 N1—C8—H8B H8A—C8—H8B S1—C9—H9A S1—C9—H9B S1—C9—H9C H9A—C9—H9B H9A—C9—H9C H9B—C9—H9C 109.00 108.00 109.00 109.00 109.00 109.00 109.00 109.00 C9—S1—C8—N1 C8—N1—C7—O1 C8—N1—C7—C1 C7—N1—C8—S1 C6—C1—C2—C3 C7—C1—C2—C3 C2—C1—C6—C5 C7—C1—C6—C5 −73.54 (15) −3.9 (2) 175.55 (13) 105.09 (16) 0.0 (2) 178.63 (15) 0.0 (2) −178.51 (15) C2—C1—C7—O1 C2—C1—C7—N1 C6—C1—C7—O1 C6—C1—C7—N1 C1—C2—C3—C4 C2—C3—C4—C5 C3—C4—C5—C6 C4—C5—C6—C1 −23.5 (2) 157.05 (14) 155.07 (15) −24.4 (2) −0.4 (3) 0.6 (3) −0.5 (3) 0.2 (3) Hydrogen-bond geometry (Å, º) D—H···A i N1—H1···O1 C8—H8B···O1ii D—H H···A D···A D—H···A 0.86 0.97 2.02 2.53 2.8438 (17) 3.434 (2) 160 154 Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x+1/2, −y+1/2, −z. Acta Cryst. (2012). E68, o653 sup-6

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