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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Pages o2291-o2292
https://doi.org/10.1107/S160053681202836X

8-Methyl-2-oxo-4-(thio­phen-2-yl)-1,2,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile

Abdullah M. Asiri,a,b‡ Hassan M. Faidallah,a Alaa Anwar Ahmad Saqer,a,b Seik Weng Ngc and Edward R. T. Tiekinkc*

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, bCenter of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 20 June 2012; accepted 22 June 2012; online 30 June 2012)

In the title compound, C15H14N2OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011 Å) and the cyclo­hexene ring has a twisted half-boat conformation with the methyl­ene C atom adjacent to the methine C atom deviating by 0.592 (7) Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108 Å). The thienyl ring is disordered over two almost coplanar positions of opposite orientation in a 0.649 (4):0.351 (4) ratio, and forms dihedral angles of 51.4 (3) (major component) and 54.2 (3)°, respectively, with the pyridinone ring. In the crystal, inversion-related mol­ecules associate via an eight-membered {⋯HNCO}2 synthon and these are linked into a linear supra­molecular chain along the a axis by weak π–π inter­actions that occur between centrosymmetrically related pyridinone rings [centroid–centroid distance = 3.889 (2) Å].

Related literature

For background to the cardiotonic and anti-inflammatory properties of this class of compounds, see: Behit & Baraka (2005[Behit, A. A. & Baraka, A. M. (2005). Eur. J. Med. Chem. 40, 1405-1413.]); Girgis et al. (2007[Girgis, A. S., Mishriky, N., Ellithey, M., Hosni, H. M. & Farag, H. (2007). Bioorg. Med. Chem. 15, 2403-2413.]). For a related structure, see: Asiri et al. (2011[Asiri, A. M., Faidallah, H. M., Al-Youbi, A. O., Alamry, K. A. & Ng, S. W. (2011). Acta Cryst. E67, o2472.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N2OS

  • Mr = 270.34

  • Triclinic, [P \overline 1]

  • a = 7.6443 (3) Å

  • b = 9.6909 (5) Å

  • c = 9.9852 (5) Å

  • α = 67.003 (5)°

  • β = 80.869 (4)°

  • γ = 76.108 (4)°

  • V = 659.26 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 100 K

  • 0.30 × 0.20 × 0.05 mm
Data collection

  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.798, Tmax = 1.000

  • 9707 measured reflections

  • 3041 independent reflections

  • 2356 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.088

  • wR(F2) = 0.230

  • S = 1.07

  • 3041 reflections

  • 185 parameters

  • 33 restraints

  • H-atom parameters constrained

  • Δρmax = 1.02 e Å−3

  • Δρmin = −0.78 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1n⋯O1i 0.88 1.94 2.801 (4) 168
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681202836X/xu5572sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202836X/xu5572Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681202836X/xu5572Isup3.cml

checkCIF report


Comment top

The title compound (I) is a member of a series of cyano-pyridinones that have been evaluated for their cardiotonic (Behit & Baraka, 2005) and anti-inflammatory (Girgis et al., (2007) properties. Herein, the crystal and molecular structures of (I) are described.

In (I), Fig. 1, the pyridyl ring in the fused ring system is planar [r.m.s. deviation = 0.011 Å] and the cyclohexene ring has a twisted half-boat conformation with the methylene-C3 atom lying -0.592 (7) Å above the plane defined by the remaining five atoms [r.m.s. deviation = 0.108 Å]. There are two orientations of the thienyl ring [co-planar, with a dihedral angle of 4.4 (4)°, and of opposite orientations] both of which are inclined with respect to the pyridyl ring, forming dihedral angles of 51.4 (3)° [major component] and 54.2 (3)°, respectively. The molecular structure of (I) resembles that found in a literature structure with the exception of the C2—C3 conformation which is fused to a benzene ring (Asiri et al., 2011).

The familiar eight-membered centrosymmetric amide {···HNCO}2 synthon is observed in the crystal packing, Table 1. These are connected into a linear supramolecular chain along the a axis by π—π interactions that occur between centrosymmetrically related pyridyl rings [inter-centroid distance = 3.889 (2) Å for symmetry operation 1 - x, 1 - y, 1 - z], Fig. 2. Chains assemble into layers in the ab plane and stack along the c axis being separated by hydrophobic interactions, Fig. 3.

Related literature top

For background to the cardiotonic and anti-inflammatory properties of this class of compounds, see: Behit & Baraka (2005); Girgis et al. (2007). For a related structure, see: Asiri et al. (2011).

Experimental top

A mixture of the thiophene-2-carboxaldehyde (1.1 g, 0.01 M), 2-methylcyclohexanone (1.12 g, 0.01 M), ethyl cyanoacetate (1.1 g, 0.01 M) and ammonium acetate (6.2 g, 0.08 M) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool. The formed precipitate was filtered, washed with water, dried and recrystallized from ethanol as yellow crystals, M. pt: 525–527 K. Yield: 72%.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95–0.99 Å, Uiso(H) = 1.2–1.5Ueq(C)] and were included in the refinement in the riding model approximation. The N-bound H-atom was treated similarly with N—H = 0.88 Å and with Uiso(H) = 1.2Ueq(N). The thienyl ring is disordered over two positions [co-planar and opposite orientation] in a 0.649 (4):0.351 (4) ratio. Pairs of 1,2-related distances were restrained to within 0.01 Å of each other, and the rings were restrained to be within 0.01 Å of a plane. The anisotropic displacement parameters, restrained to be nearly isotropic, of the primed atoms were set to those of the unprimed ones. The maximum and minimum residual electron density peaks of 1.02 and -0.78 e Å-3, respectively, were located 0.14 Å and 0.39 Å from the C15' and C13 atoms, respectively.

Structure description top

The title compound (I) is a member of a series of cyano-pyridinones that have been evaluated for their cardiotonic (Behit & Baraka, 2005) and anti-inflammatory (Girgis et al., (2007) properties. Herein, the crystal and molecular structures of (I) are described.

In (I), Fig. 1, the pyridyl ring in the fused ring system is planar [r.m.s. deviation = 0.011 Å] and the cyclohexene ring has a twisted half-boat conformation with the methylene-C3 atom lying -0.592 (7) Å above the plane defined by the remaining five atoms [r.m.s. deviation = 0.108 Å]. There are two orientations of the thienyl ring [co-planar, with a dihedral angle of 4.4 (4)°, and of opposite orientations] both of which are inclined with respect to the pyridyl ring, forming dihedral angles of 51.4 (3)° [major component] and 54.2 (3)°, respectively. The molecular structure of (I) resembles that found in a literature structure with the exception of the C2—C3 conformation which is fused to a benzene ring (Asiri et al., 2011).

The familiar eight-membered centrosymmetric amide {···HNCO}2 synthon is observed in the crystal packing, Table 1. These are connected into a linear supramolecular chain along the a axis by π—π interactions that occur between centrosymmetrically related pyridyl rings [inter-centroid distance = 3.889 (2) Å for symmetry operation 1 - x, 1 - y, 1 - z], Fig. 2. Chains assemble into layers in the ab plane and stack along the c axis being separated by hydrophobic interactions, Fig. 3.

For background to the cardiotonic and anti-inflammatory properties of this class of compounds, see: Behit & Baraka (2005); Girgis et al. (2007). For a related structure, see: Asiri et al. (2011).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A view of the supramolecular chain along the a axis in (I) mediated by N—H···O and π—π interactions, shown as orange and purple dashed lines, respectively.
[Figure 3] Fig. 3. A view in projection down the b axis of the unit-cell contents of (I). The N—H···O and π—π interactions are shown as orange and purple dashed lines, respectively.
8-Methyl-2-oxo-4-(thiophen-2-yl)-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile top
Crystal data top
C15H14N2OSZ = 2
Mr = 270.34F(000) = 284
Triclinic, P1Dx = 1.362 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6443 (3) ÅCell parameters from 3729 reflections
b = 9.6909 (5) Åθ = 2.3–27.5°
c = 9.9852 (5) ŵ = 0.24 mm−1
α = 67.003 (5)°T = 100 K
β = 80.869 (4)°Plate, yellow
γ = 76.108 (4)°0.30 × 0.20 × 0.05 mm
V = 659.26 (5) Å3
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		3041 independent reflections
Radiation source: SuperNova (Mo) X-ray Source2356 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.031
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 2.3°
ω scanh = −9→9
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)		k = −12→12
Tmin = 0.798, Tmax = 1.000l = −12→12
9707 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.088Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0899P)2 + 1.5187P]
where P = (Fo2 + 2Fc2)/3
3041 reflections(Δ/σ)max = 0.001
185 parametersΔρmax = 1.02 e Å−3
33 restraintsΔρmin = −0.78 e Å−3
Crystal data top
C15H14N2OSγ = 76.108 (4)°
Mr = 270.34V = 659.26 (5) Å3
Triclinic, P1Z = 2
a = 7.6443 (3) ÅMo Kα radiation
b = 9.6909 (5) ŵ = 0.24 mm−1
c = 9.9852 (5) ÅT = 100 K
α = 67.003 (5)°0.30 × 0.20 × 0.05 mm
β = 80.869 (4)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		3041 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)		2356 reflections with I > 2σ(I)
Tmin = 0.798, Tmax = 1.000Rint = 0.031
9707 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08833 restraints
wR(F2) = 0.230H-atom parameters constrained
S = 1.07Δρmax = 1.02 e Å−3
3041 reflectionsΔρmin = −0.78 e Å−3
185 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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) top
xyzUiso*/UeqOcc. (<1)
O10.8432 (4)0.6552 (5)0.4105 (4)0.0607 (13)
N10.7871 (4)0.4615 (4)0.6240 (4)0.0359 (9)
H1n0.89840.41180.61600.043*
N20.4540 (5)0.9325 (4)0.3270 (4)0.0359 (9)
C10.9207 (6)0.2563 (6)0.9181 (5)0.0405 (11)
H1A1.00510.31020.84230.061*
H1B0.98470.15460.97650.061*
H1C0.87020.31440.98130.061*
C20.7691 (5)0.2402 (5)0.8473 (4)0.0303 (9)
H20.82460.17550.78840.036*
C30.6307 (6)0.1585 (5)0.9600 (5)0.0337 (10)
H3A0.56680.11200.91470.040*
H3B0.69410.07521.04220.040*
C40.4947 (6)0.2674 (5)1.0173 (5)0.0361 (10)
H4A0.55840.31541.06110.043*
H4B0.41210.21011.09450.043*
C50.3854 (5)0.3914 (5)0.8953 (4)0.0300 (9)
H5A0.30150.34580.86670.036*
H5B0.31200.47030.93180.036*
C60.5042 (5)0.4659 (4)0.7629 (4)0.0219 (7)
C70.6793 (5)0.3935 (4)0.7432 (4)0.0244 (8)
C80.7363 (5)0.6006 (5)0.5159 (5)0.0367 (11)
C90.5537 (5)0.6763 (4)0.5364 (4)0.0252 (8)
C100.4413 (5)0.6133 (4)0.6569 (4)0.0204 (7)
C110.4972 (5)0.8193 (5)0.4214 (4)0.0258 (8)
C120.2592 (5)0.7030 (4)0.6738 (4)0.0311 (9)
S10.0646 (2)0.6528 (2)0.7033 (2)0.0426 (7)0.649 (4)
S1'0.2014 (7)0.8647 (5)0.6683 (4)0.043*0.351 (4)
C130.260 (2)0.8772 (14)0.6570 (7)0.069 (4)0.649 (4)
H130.35590.93060.63990.082*0.649 (4)
C13'0.079 (2)0.627 (2)0.6905 (12)0.069*0.351 (4)
H13'0.07140.52850.69710.082*0.351 (4)
C140.0544 (12)0.9255 (9)0.6783 (8)0.0461 (18)0.649 (4)
H140.00311.02610.67520.055*0.649 (4)
C14'−0.072 (2)0.7647 (18)0.6921 (14)0.046*0.351 (4)
H14'−0.19610.76000.69920.055*0.351 (4)
C15−0.0505 (11)0.8293 (9)0.7006 (7)0.0432 (18)0.649 (4)
H15−0.17830.85450.71410.052*0.649 (4)
C15'−0.0217 (15)0.8881 (17)0.6833 (11)0.043*0.351 (4)
H15'−0.10230.97880.68520.052*0.351 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0203 (15)0.071 (3)0.0354 (18)0.0116 (15)0.0094 (13)0.0234 (17)
N10.0157 (15)0.041 (2)0.0255 (18)0.0083 (14)0.0040 (13)0.0050 (15)
N20.0270 (18)0.035 (2)0.0275 (18)0.0013 (15)−0.0005 (14)0.0029 (15)
C10.026 (2)0.045 (3)0.031 (2)−0.0043 (18)−0.0045 (17)0.0055 (19)
C20.026 (2)0.027 (2)0.025 (2)0.0028 (15)−0.0006 (15)−0.0016 (16)
C30.031 (2)0.0230 (19)0.032 (2)−0.0038 (16)−0.0018 (17)0.0049 (16)
C40.030 (2)0.034 (2)0.025 (2)−0.0049 (17)0.0056 (16)0.0047 (17)
C50.0189 (18)0.030 (2)0.029 (2)−0.0054 (15)0.0050 (15)0.0000 (16)
C60.0180 (17)0.0239 (18)0.0205 (17)−0.0050 (13)−0.0003 (13)−0.0046 (14)
C70.0197 (17)0.0267 (19)0.0202 (17)−0.0022 (14)0.0012 (13)−0.0039 (15)
C80.0157 (18)0.045 (2)0.024 (2)0.0044 (16)0.0023 (14)0.0071 (18)
C90.0174 (17)0.0285 (19)0.0209 (18)−0.0013 (14)−0.0021 (13)−0.0013 (15)
C100.0151 (16)0.0236 (17)0.0213 (17)−0.0047 (13)−0.0007 (13)−0.0067 (14)
C110.0164 (17)0.031 (2)0.0221 (18)−0.0023 (14)0.0006 (13)−0.0034 (16)
C120.0238 (19)0.035 (2)0.0189 (18)0.0049 (16)0.0027 (14)−0.0018 (16)
S10.0090 (7)0.0483 (10)0.0447 (10)−0.0033 (6)−0.0002 (5)0.0084 (7)
C130.069 (4)0.069 (4)0.068 (4)−0.0132 (15)−0.0044 (13)−0.0250 (18)
C140.046 (2)0.045 (2)0.043 (2)−0.0018 (12)0.0006 (12)−0.0171 (13)
C150.040 (2)0.042 (2)0.041 (2)−0.0030 (12)0.0010 (12)−0.0128 (13)
Geometric parameters (Å, º) top
O1—C81.246 (5)C6—C101.429 (5)
N1—C71.366 (5)C8—C91.436 (5)
N1—C81.371 (5)C9—C101.381 (5)
N1—H1n0.8800C9—C111.433 (5)
N2—C111.148 (5)C10—C121.477 (5)
C1—C21.516 (6)C12—S1'1.503 (5)
C1—H1A0.9800C12—S11.622 (4)
C1—H1B0.9800C12—C131.632 (13)
C1—H1C0.9800C12—C13'1.668 (17)
C2—C71.513 (5)S1—C151.717 (8)
C2—C31.530 (5)S1'—C15'1.656 (11)
C2—H21.0000C13—C141.537 (15)
C3—C41.510 (6)C13—H130.9500
C3—H3A0.9900C13'—C14'1.541 (18)
C3—H3B0.9900C13'—H13'0.9500
C4—C51.524 (6)C14—C151.304 (12)
C4—H4A0.9900C14—H140.9500
C4—H4B0.9900C14'—C15'1.309 (15)
C5—C61.511 (5)C14'—H14'0.9500
C5—H5A0.9900C15—H150.9500
C5—H5B0.9900C15'—H15'0.9500
C6—C71.377 (5)
C7—N1—C8125.4 (3)O1—C8—N1121.6 (4)
C7—N1—H1n117.3O1—C8—C9124.0 (4)
C8—N1—H1n117.3N1—C8—C9114.4 (3)
C2—C1—H1A109.5C10—C9—C11123.1 (3)
C2—C1—H1B109.5C10—C9—C8122.1 (3)
H1A—C1—H1B109.5C11—C9—C8114.9 (3)
C2—C1—H1C109.5C9—C10—C6119.8 (3)
H1A—C1—H1C109.5C9—C10—C12118.5 (3)
H1B—C1—H1C109.5C6—C10—C12121.7 (3)
C7—C2—C1111.3 (4)N2—C11—C9178.5 (4)
C7—C2—C3111.3 (3)C10—C12—S1'130.3 (4)
C1—C2—C3112.2 (4)C10—C12—S1129.1 (3)
C7—C2—H2107.3S1'—C12—S1100.5 (3)
C1—C2—H2107.3C10—C12—C13113.3 (6)
C3—C2—H2107.3S1—C12—C13117.5 (6)
C4—C3—C2111.4 (3)C10—C12—C13'119.2 (8)
C4—C3—H3A109.4S1'—C12—C13'110.3 (8)
C2—C3—H3A109.4C13—C12—C13'127.1 (11)
C4—C3—H3B109.4C12—S1—C1592.6 (4)
C2—C3—H3B109.4C12—S1'—C15'102.2 (6)
H3A—C3—H3B108.0C14—C13—C1295.8 (9)
C3—C4—C5110.8 (4)C14—C13—H13132.1
C3—C4—H4A109.5C12—C13—H13132.1
C5—C4—H4A109.5C14'—C13'—C1299.6 (13)
C3—C4—H4B109.5C14'—C13'—H13'130.2
C5—C4—H4B109.5C12—C13'—H13'130.2
H4A—C4—H4B108.1C15—C14—C13120.5 (8)
C6—C5—C4112.3 (3)C15—C14—H14119.8
C6—C5—H5A109.2C13—C14—H14119.8
C4—C5—H5A109.2C15'—C14'—C13'117.0 (15)
C6—C5—H5B109.2C15'—C14'—H14'121.5
C4—C5—H5B109.2C13'—C14'—H14'121.5
H5A—C5—H5B107.9C14—C15—S1113.6 (6)
C7—C6—C10118.1 (3)C14—C15—H15123.2
C7—C6—C5120.2 (3)S1—C15—H15123.2
C10—C6—C5121.7 (3)C14'—C15'—S1'110.9 (12)
N1—C7—C6120.2 (3)C14'—C15'—H15'124.6
N1—C7—C2114.9 (3)S1'—C15'—H15'124.6
C6—C7—C2124.9 (3)
C7—C2—C3—C4−42.7 (5)C9—C10—C12—S1'−51.3 (6)
C1—C2—C3—C482.7 (5)C6—C10—C12—S1'127.3 (4)
C2—C3—C4—C562.8 (5)C9—C10—C12—S1128.4 (4)
C3—C4—C5—C6−49.6 (5)C6—C10—C12—S1−52.9 (5)
C4—C5—C6—C719.3 (6)C9—C10—C12—C13−50.5 (4)
C4—C5—C6—C10−159.4 (4)C6—C10—C12—C13128.2 (4)
C8—N1—C7—C6−0.6 (7)C9—C10—C12—C13'123.6 (5)
C8—N1—C7—C2−179.4 (4)C6—C10—C12—C13'−57.7 (5)
C10—C6—C7—N1−0.8 (6)C10—C12—S1—C15−178.7 (4)
C5—C6—C7—N1−179.5 (4)S1'—C12—S1—C151.1 (3)
C10—C6—C7—C2177.8 (4)C13—C12—S1—C150.15 (17)
C5—C6—C7—C2−1.0 (6)C13'—C12—S1—C15−155 (3)
C1—C2—C7—N165.3 (5)C10—C12—S1'—C15'175.7 (5)
C3—C2—C7—N1−168.7 (4)S1—C12—S1'—C15'−4.1 (4)
C1—C2—C7—C6−113.3 (5)C13—C12—S1'—C15'173.1 (11)
C3—C2—C7—C612.6 (6)C13'—C12—S1'—C15'0.42 (19)
C7—N1—C8—O1179.8 (5)C10—C12—C13—C14178.9 (4)
C7—N1—C8—C90.7 (7)S1'—C12—C13—C14−3.2 (10)
O1—C8—C9—C10−178.3 (5)S1—C12—C13—C14−0.1 (2)
N1—C8—C9—C100.8 (7)C13'—C12—C13—C145.4 (5)
O1—C8—C9—C113.1 (7)C10—C12—C13'—C14'−175.7 (4)
N1—C8—C9—C11−177.9 (4)S1'—C12—C13'—C14'0.2 (2)
C11—C9—C10—C6176.3 (4)S1—C12—C13'—C14'25 (3)
C8—C9—C10—C6−2.2 (6)C13—C12—C13'—C14'−2.5 (5)
C11—C9—C10—C12−5.0 (6)C12—C13—C14—C150.0 (4)
C8—C9—C10—C12176.4 (4)C12—C13'—C14'—C15'−1.0 (5)
C7—C6—C10—C92.2 (5)C13—C14—C15—S10.1 (6)
C5—C6—C10—C9−179.1 (4)C12—S1—C15—C14−0.2 (4)
C7—C6—C10—C12−176.4 (4)C13'—C14'—C15'—S1'1.3 (6)
C5—C6—C10—C122.3 (6)C12—S1'—C15'—C14'−1.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O1i0.881.942.801 (4)168
Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC15H14N2OS
Mr270.34
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.6443 (3), 9.6909 (5), 9.9852 (5)
α, β, γ (°)67.003 (5), 80.869 (4), 76.108 (4)
V (Å3)659.26 (5)
Z2
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.30 × 0.20 × 0.05
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.798, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		9707, 3041, 2356
Rint0.031
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.088, 0.230, 1.07
No. of reflections3041
No. of parameters185
No. of restraints33
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.02, −0.78

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···O1i0.881.942.801 (4)167.5
Symmetry code: (i) −x+2, −y+1, −z+1.
 

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are grateful to King Abdulaziz University for providing the research facilities. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.  Google Scholar
 First citationAsiri, A. M., Faidallah, H. M., Al-Youbi, A. O., Alamry, K. A. & Ng, S. W. (2011). Acta Cryst. E67, o2472.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBehit, A. A. & Baraka, A. M. (2005). Eur. J. Med. Chem. 40, 1405–1413.  Web of Science PubMed Google Scholar
 First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGirgis, A. S., Mishriky, N., Ellithey, M., Hosni, H. M. & Farag, H. (2007). Bioorg. Med. Chem. 15, 2403–2413.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Pages o2291-o2292
https://doi.org/10.1107/S160053681202836X
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