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ISSN: 2056-9890

(E)-3-Anilino-2-benzoyl-3-(methyl­sulfan­yl)acrylo­nitrile

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 27 March 2012; accepted 28 March 2012; online 31 March 2012)

In the title acrylonitrile derivative, C17H14N2OS, the central amino­acryl­aldehyde O=C—C=C—NH unit, wherein an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif, is approximately planar, with an r.m.s. deviation of 0.0234 (2) Å for the five non-H atoms. This plane makes dihedral angles of 41.04 (9) and 84.86 (10)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 54.82 (10)°. An intra­molecular C—H⋯N hydrogen bond is also present. In the crystal, weak C—H⋯π and ππ inter­actions, with a centroid–centroid distance of 3.8526 (14) Å, are observed.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002[Saufi, S. M. & Ismail, A. F. (2002). Songklanakarin J. Sci. Technol. 24(Suppl.), 843-854.]); Sączewski et al. (2004[Sączewski, F., Reszka, P., Gdaniec, M., Grünert, R. & Bednarski, P. J. (2004). J. Med. Chem. 47, 3438-3449.]); Sommen et al. (2002[Sommen, G., Comel, A. & Kirsch, G. (2002). Tetrahedron Lett. 43, 257-260.], 2003[Sommen, G., Comel, A. & Kirsch, G. (2003). Tetrahedron, 59, 1557-1564.]); Rudorf & Augustin (1977[Rudorf, W.-D. & Augustin, M. (1977). J. Prakt. Chem. 319, 545-560.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14N2OS

  • Mr = 294.37

  • Monoclinic, P 21 /c

  • a = 8.7522 (2) Å

  • b = 10.8464 (3) Å

  • c = 16.1156 (4) Å

  • β = 103.968 (2)°

  • V = 1484.62 (7) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 1.93 mm−1

  • T = 296 K

  • 0.58 × 0.52 × 0.34 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.401, Tmax = 0.556

  • 9777 measured reflections

  • 2603 independent reflections

  • 2403 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.109

  • S = 1.04

  • 2603 reflections

  • 197 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N1⋯O1 0.91 (3) 1.86 (3) 2.610 (2) 137 (2)
C11—H11B⋯N2 0.96 2.60 3.372 (2) 138
C17—H17ACg1i 0.93 2.91 3.690 (2) 143
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Acrylonitrile derivatives play many important roles in chemistry such as in membrane technology (Saufi & Ismail, 2002), synthesis and medicinal chemistry (Sączewski et al., 2004; Sommen et al., 2002, 2003). 2,3-Disubstituted acrylonitriles represent an interesting class of biologically active compounds, many of them possess cytotoxicity (Sączewski et al., 2004). These interesting acrylonitrile derivatives promted us to synthesize the title acrylonitrile derivative (I) in order to study for its biological activity. Herein the crystal structure of (I) was reported.

The molecule of the title acrylonitrile derivative, C17H14N2OS, exists in an E configuration with respect to the olifinic C8C9 double bond [1.412 (2) Å] and with torsion angles C10–C8–C9–N1 = 162.52 (16)° and C7–C8–C9–S1 = 173.43 (12)° (Fig. 1). The molecule is twisted with the dihedral angle between the two phenyl rings being 54.82 (10)°. Atoms of the middle fragment of the central aminoacrylaldehyde unit (C7–C9/O1/N1) lie roughly on the same plane with an r.m.s. deviation of 0.0234 (2) Å for the five non-H atoms (C7–C9/O1/N1). An intramolecular N1—H1N1···O1 hydrogen bond (Table 1) generates an S(6) ring motif (Fig. 1) (Bernstein et al., 1995), which helps to stabilize the planarity of this plane. The mean plane through the C7/C8/C9/O1/N1 atoms makes dihedral angles of 41.04 (9) and 84.86 (10)° with the benzoyl and aminophenyl rings, respectively. The orientation of the methylthio group with respect to the olefinic moiety is indicated by the torsion angle C11–S1–C9–C8 = -42.56 (16)°. The dihedral angle between the two mean planes of N2/C10/C8/C9 and C8/C9/S1/C11 is 47.08 (15)°. An intramolecular weak C—H···N interaction generates an S(7) ring motif (Bernstein et al., 1995). The bond distances of (I) are within normal ranges (Allen et al., 1987).

The crystal packing of (I) is stabilized by weak C—H···π interactions (Table 1). A ππ interaction (Fig. 2) between the two aminophenyl rings with the distance of Cg2···Cg2ii = 3.8526 (14) Å [symmetry code (ii) = 1-x, 1-y, -z] was presented; Cg2 is the centroid of the C12–C17 ring.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002); Sączewski et al. (2004); Sommen et al. (2002, 2003); Rudorf & Augustin (1977).

Experimental top

The title compound was prepared according to the reported method (Rudorf et al., 1977). Single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by the slow evaporation of the solvent at room temperature after several days.

Refinement top

Amino H atom was located in a difference Fourier map and refined isotropically [N—H = 0.91 (3) Å]. The remaining H atoms were placed in calculated positions with d(C—H) = 0.93 for aromatic and 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Structure description top

Acrylonitrile derivatives play many important roles in chemistry such as in membrane technology (Saufi & Ismail, 2002), synthesis and medicinal chemistry (Sączewski et al., 2004; Sommen et al., 2002, 2003). 2,3-Disubstituted acrylonitriles represent an interesting class of biologically active compounds, many of them possess cytotoxicity (Sączewski et al., 2004). These interesting acrylonitrile derivatives promted us to synthesize the title acrylonitrile derivative (I) in order to study for its biological activity. Herein the crystal structure of (I) was reported.

The molecule of the title acrylonitrile derivative, C17H14N2OS, exists in an E configuration with respect to the olifinic C8C9 double bond [1.412 (2) Å] and with torsion angles C10–C8–C9–N1 = 162.52 (16)° and C7–C8–C9–S1 = 173.43 (12)° (Fig. 1). The molecule is twisted with the dihedral angle between the two phenyl rings being 54.82 (10)°. Atoms of the middle fragment of the central aminoacrylaldehyde unit (C7–C9/O1/N1) lie roughly on the same plane with an r.m.s. deviation of 0.0234 (2) Å for the five non-H atoms (C7–C9/O1/N1). An intramolecular N1—H1N1···O1 hydrogen bond (Table 1) generates an S(6) ring motif (Fig. 1) (Bernstein et al., 1995), which helps to stabilize the planarity of this plane. The mean plane through the C7/C8/C9/O1/N1 atoms makes dihedral angles of 41.04 (9) and 84.86 (10)° with the benzoyl and aminophenyl rings, respectively. The orientation of the methylthio group with respect to the olefinic moiety is indicated by the torsion angle C11–S1–C9–C8 = -42.56 (16)°. The dihedral angle between the two mean planes of N2/C10/C8/C9 and C8/C9/S1/C11 is 47.08 (15)°. An intramolecular weak C—H···N interaction generates an S(7) ring motif (Bernstein et al., 1995). The bond distances of (I) are within normal ranges (Allen et al., 1987).

The crystal packing of (I) is stabilized by weak C—H···π interactions (Table 1). A ππ interaction (Fig. 2) between the two aminophenyl rings with the distance of Cg2···Cg2ii = 3.8526 (14) Å [symmetry code (ii) = 1-x, 1-y, -z] was presented; Cg2 is the centroid of the C12–C17 ring.

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to the synthesis and chemistry of acrylonitrile derivatives, see: Saufi & Ismail (2002); Sączewski et al. (2004); Sommen et al. (2002, 2003); Rudorf & Augustin (1977).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular N—H···O hydrogen bond is shown as a dash line.
[Figure 2] Fig. 2. A crystal packing diagram of the title compound, viewed along the approximately along the a axis, showing the ππ interaction (dashed line) between the aminophenyl rings. H atoms were omitted for clarity.
(E)-3-Anilino-2-benzoyl-3-(methylsulfanyl)acrylonitrile top
Crystal data top
C17H14N2OSF(000) = 616
Mr = 294.37Dx = 1.317 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 2603 reflections
a = 8.7522 (2) Åθ = 5.0–67.5°
b = 10.8464 (3) ŵ = 1.93 mm1
c = 16.1156 (4) ÅT = 296 K
β = 103.968 (2)°Block, colorless
V = 1484.62 (7) Å30.58 × 0.52 × 0.34 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
2603 independent reflections
Radiation source: fine-focus sealed tube2403 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 67.5°, θmin = 5.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 810
Tmin = 0.401, Tmax = 0.556k = 1212
9777 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.3429P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2603 reflectionsΔρmax = 0.23 e Å3
197 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0100 (8)
Crystal data top
C17H14N2OSV = 1484.62 (7) Å3
Mr = 294.37Z = 4
Monoclinic, P21/cCu Kα radiation
a = 8.7522 (2) ŵ = 1.93 mm1
b = 10.8464 (3) ÅT = 296 K
c = 16.1156 (4) Å0.58 × 0.52 × 0.34 mm
β = 103.968 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
2603 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2403 reflections with I > 2σ(I)
Tmin = 0.401, Tmax = 0.556Rint = 0.024
9777 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.23 e Å3
2603 reflectionsΔρmin = 0.23 e Å3
197 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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 > 2sigma(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) top
xyzUiso*/Ueq
S10.26713 (5)0.35557 (4)0.12096 (3)0.05369 (19)
O10.76575 (17)0.35293 (12)0.07292 (10)0.0674 (4)
N10.48494 (19)0.25937 (13)0.05485 (10)0.0525 (4)
N20.4752 (2)0.65992 (13)0.16908 (13)0.0639 (4)
C10.84541 (18)0.53504 (14)0.14953 (10)0.0427 (4)
C20.9477 (2)0.57125 (16)0.10025 (11)0.0520 (4)
H2A0.93700.53750.04610.062*
C31.0652 (2)0.65671 (18)0.13054 (15)0.0630 (5)
H3A1.13170.68130.09650.076*
C41.0834 (2)0.70502 (17)0.21094 (15)0.0649 (5)
H4A1.16280.76210.23160.078*
C50.9841 (2)0.66911 (18)0.26115 (13)0.0605 (5)
H5A0.99770.70160.31590.073*
C60.8640 (2)0.58504 (16)0.23089 (11)0.0507 (4)
H6A0.79640.56230.26480.061*
C70.7250 (2)0.43946 (15)0.11312 (10)0.0471 (4)
C80.56634 (19)0.45013 (14)0.12432 (10)0.0439 (4)
C90.4545 (2)0.35497 (13)0.09959 (10)0.0438 (4)
C100.51581 (19)0.56593 (14)0.15039 (11)0.0469 (4)
C110.3008 (2)0.40943 (17)0.22941 (11)0.0557 (4)
H11A0.21200.38870.25190.084*
H11B0.31460.49730.23070.084*
H11C0.39370.37110.26350.084*
C120.3870 (2)0.15146 (13)0.03407 (11)0.0446 (4)
C130.4078 (3)0.05512 (18)0.09040 (12)0.0640 (5)
H13A0.48380.05950.14180.077*
C140.3149 (3)0.04908 (18)0.07019 (14)0.0696 (6)
H14A0.32810.11480.10830.084*
C150.2036 (3)0.05567 (17)0.00557 (13)0.0624 (5)
H15A0.14110.12560.01890.075*
C160.1846 (3)0.04131 (19)0.06189 (13)0.0680 (5)
H16A0.10870.03690.11330.082*
C170.2775 (3)0.14547 (16)0.04263 (12)0.0580 (5)
H17A0.26590.21060.08120.070*
H1N10.578 (3)0.265 (2)0.0390 (16)0.083 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0462 (3)0.0578 (3)0.0579 (3)0.00653 (16)0.01425 (19)0.01599 (17)
O10.0598 (8)0.0556 (8)0.0942 (10)0.0063 (6)0.0328 (7)0.0289 (7)
N10.0539 (9)0.0434 (7)0.0649 (9)0.0093 (6)0.0235 (7)0.0163 (6)
N20.0534 (9)0.0381 (8)0.1009 (13)0.0011 (6)0.0200 (8)0.0108 (7)
C10.0400 (8)0.0378 (7)0.0502 (8)0.0055 (6)0.0105 (6)0.0008 (6)
C20.0481 (9)0.0536 (9)0.0564 (9)0.0045 (7)0.0164 (7)0.0001 (7)
C30.0478 (10)0.0568 (11)0.0874 (14)0.0016 (8)0.0224 (9)0.0082 (9)
C40.0455 (9)0.0486 (10)0.0956 (14)0.0029 (7)0.0071 (9)0.0058 (9)
C50.0538 (10)0.0562 (10)0.0638 (11)0.0083 (8)0.0007 (8)0.0141 (8)
C60.0484 (9)0.0517 (9)0.0516 (9)0.0048 (7)0.0111 (7)0.0011 (7)
C70.0495 (9)0.0400 (8)0.0528 (9)0.0006 (7)0.0140 (7)0.0032 (6)
C80.0449 (8)0.0358 (7)0.0513 (8)0.0014 (6)0.0123 (7)0.0048 (6)
C90.0474 (9)0.0384 (8)0.0448 (8)0.0001 (6)0.0094 (6)0.0016 (6)
C100.0422 (8)0.0379 (8)0.0602 (9)0.0042 (6)0.0115 (7)0.0026 (7)
C110.0698 (11)0.0484 (9)0.0520 (9)0.0024 (8)0.0207 (8)0.0035 (7)
C120.0482 (9)0.0361 (8)0.0520 (9)0.0015 (6)0.0170 (7)0.0088 (6)
C130.0721 (12)0.0561 (10)0.0566 (10)0.0033 (9)0.0014 (9)0.0047 (8)
C140.0857 (14)0.0452 (10)0.0781 (13)0.0034 (9)0.0200 (11)0.0149 (9)
C150.0684 (12)0.0427 (9)0.0803 (13)0.0132 (8)0.0260 (10)0.0120 (8)
C160.0713 (12)0.0612 (11)0.0638 (11)0.0144 (9)0.0015 (9)0.0082 (9)
C170.0689 (12)0.0443 (9)0.0576 (10)0.0052 (8)0.0089 (9)0.0030 (7)
Geometric parameters (Å, º) top
S1—C91.7549 (17)C6—H6A0.9300
S1—C111.7983 (17)C7—C81.447 (2)
O1—C71.241 (2)C8—C91.412 (2)
N1—C91.326 (2)C8—C101.428 (2)
N1—C121.441 (2)C11—H11A0.9600
N1—H1N10.91 (3)C11—H11B0.9600
N2—C101.144 (2)C11—H11C0.9600
C1—C21.389 (2)C12—C131.367 (3)
C1—C61.392 (2)C12—C171.371 (3)
C1—C71.494 (2)C13—C141.385 (3)
C2—C31.383 (3)C13—H13A0.9300
C2—H2A0.9300C14—C151.367 (3)
C3—C41.371 (3)C14—H14A0.9300
C3—H3A0.9300C15—C161.373 (3)
C4—C51.379 (3)C15—H15A0.9300
C4—H4A0.9300C16—C171.383 (3)
C5—C61.388 (3)C16—H16A0.9300
C5—H5A0.9300C17—H17A0.9300
C9—S1—C11104.50 (9)N1—C9—C8120.54 (16)
C9—N1—C12125.09 (15)N1—C9—S1115.44 (13)
C9—N1—H1N1114.4 (17)C8—C9—S1123.98 (12)
C12—N1—H1N1120.4 (17)N2—C10—C8178.1 (2)
C2—C1—C6118.92 (15)S1—C11—H11A109.5
C2—C1—C7117.55 (14)S1—C11—H11B109.5
C6—C1—C7123.47 (15)H11A—C11—H11B109.5
C3—C2—C1120.98 (17)S1—C11—H11C109.5
C3—C2—H2A119.5H11A—C11—H11C109.5
C1—C2—H2A119.5H11B—C11—H11C109.5
C4—C3—C2119.76 (19)C13—C12—C17120.98 (16)
C4—C3—H3A120.1C13—C12—N1119.33 (16)
C2—C3—H3A120.1C17—C12—N1119.67 (15)
C3—C4—C5120.06 (17)C12—C13—C14119.40 (18)
C3—C4—H4A120.0C12—C13—H13A120.3
C5—C4—H4A120.0C14—C13—H13A120.3
C4—C5—C6120.69 (18)C15—C14—C13120.27 (18)
C4—C5—H5A119.7C15—C14—H14A119.9
C6—C5—H5A119.7C13—C14—H14A119.9
C5—C6—C1119.58 (17)C14—C15—C16119.79 (17)
C5—C6—H6A120.2C14—C15—H15A120.1
C1—C6—H6A120.2C16—C15—H15A120.1
O1—C7—C8122.07 (15)C15—C16—C17120.44 (18)
O1—C7—C1117.75 (15)C15—C16—H16A119.8
C8—C7—C1120.17 (13)C17—C16—H16A119.8
C9—C8—C10118.88 (15)C12—C17—C16119.11 (17)
C9—C8—C7121.80 (14)C12—C17—H17A120.4
C10—C8—C7118.79 (14)C16—C17—H17A120.4
C6—C1—C2—C30.8 (2)C12—N1—C9—S19.1 (2)
C7—C1—C2—C3178.16 (16)C10—C8—C9—N1162.52 (16)
C1—C2—C3—C41.2 (3)C7—C8—C9—N19.0 (2)
C2—C3—C4—C50.5 (3)C10—C8—C9—S115.0 (2)
C3—C4—C5—C60.7 (3)C7—C8—C9—S1173.43 (12)
C4—C5—C6—C11.0 (3)C11—S1—C9—N1139.77 (13)
C2—C1—C6—C50.3 (2)C11—S1—C9—C842.56 (16)
C7—C1—C6—C5176.88 (15)C9—N1—C12—C1387.4 (2)
C2—C1—C7—O139.4 (2)C9—N1—C12—C1794.4 (2)
C6—C1—C7—O1137.81 (18)C17—C12—C13—C141.2 (3)
C2—C1—C7—C8139.89 (16)N1—C12—C13—C14179.41 (19)
C6—C1—C7—C842.9 (2)C12—C13—C14—C150.2 (3)
O1—C7—C8—C98.1 (3)C13—C14—C15—C160.2 (3)
C1—C7—C8—C9172.59 (14)C14—C15—C16—C170.2 (3)
O1—C7—C8—C10163.40 (17)C13—C12—C17—C161.6 (3)
C1—C7—C8—C1015.9 (2)N1—C12—C17—C16179.83 (18)
C12—N1—C9—C8173.11 (16)C15—C16—C17—C121.1 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O10.91 (3)1.86 (3)2.610 (2)137 (2)
C11—H11B···N20.962.603.372 (2)138
C17—H17A···Cg1i0.932.913.690 (2)143
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H14N2OS
Mr294.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.7522 (2), 10.8464 (3), 16.1156 (4)
β (°) 103.968 (2)
V3)1484.62 (7)
Z4
Radiation typeCu Kα
µ (mm1)1.93
Crystal size (mm)0.58 × 0.52 × 0.34
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.401, 0.556
No. of measured, independent and
observed [I > 2σ(I)] reflections
9777, 2603, 2403
Rint0.024
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.109, 1.04
No. of reflections2603
No. of parameters197
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 benzene ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O10.91 (3)1.86 (3)2.610 (2)137 (2)
C11—H11B···N20.962.603.372 (2)138
C17—H17A···Cg1i0.932.913.690 (2)143
Symmetry code: (i) x+1, y+1, z.
 

Footnotes

Thomson Reuters ResearcherID: A-5085-2009.

§College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and SC thank the Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

References

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