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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 67| Part 10| October 2011| Page o2639
https://doi.org/10.1107/S160053681103666X

2-(1H-1,3-Benzo­diazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone

Hatem A. Abdel-Aziz,a‡ Seik Weng Ngb,c and Edward R. T. Tiekinkb*

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of, Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 14 August 2011; accepted 8 September 2011; online 14 September 2011)

The mol­ecule in the structure of the title compound, C15H11ClN2OS, displays two planar residues [r.m.s. deviation = 0.014 Å for the benzimidazole residue, and the ketone group is co-planar with the benzene ring to which it is attached forming a O—C—C—C torsion angle of −173.18 (14) °] linked at the S atom. The overall shape is based on a twisted V, the dihedral angle formed between the two planes being 82.4 (2) °. The amine-H atom is bifurcated, forming N—H⋯O and N—H⋯S hydrogen bonds leading to dimeric aggregates. These are linked into a supra­molecular chain along the c axis via C—H⋯π hydrogen bonds. Chains form layers in the ab plane being connected along the c axis via weak π–π inter­actions [3.9578 (8) Å] formed between centrosymmetrically related chloro-substituted benzene rings.

Related literature

For the biological and pharmacological properties of benzim­idazoles, see: Al-Rashood & Abdel-Aziz (2010[Al-Rashood, K. A. & Abdel-Aziz, H. A. (2010). Molecules, 15, 3775-3815.]); Abdel-Aziz et al. (2010[Abdel-Aziz, H. A., Saleh, T. S. & El-Zahabi, H. S. A. (2010). Arch. Pharm. 343, 24-30.]). For the synthesis, see: Sarhan et al. (1996[Sarhan, A. A. O., El-Shereif, H. A. H. & Mahmoud, A. M. (1996). Tetrahedron, 52, 10485-10496.]). For a related structure, see: Lynch & McClenaghan (2004[Lynch, D. E. & McClenaghan, I. (2004). Acta Cryst. E60, o363-o364.]).

[Scheme 1]

Experimental

Crystal data

  • C15H11ClN2OS

  • Mr = 302.77

  • Monoclinic, C 2/c

  • a = 27.3765 (4) Å

  • b = 9.2784 (2) Å

  • c = 10.3630 (2) Å

  • β = 93.087 (1)°

  • V = 2628.49 (9) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 4.02 mm−1

  • T = 100 K

  • 0.40 × 0.30 × 0.20 mm
Data collection

  • Agilent SuperNova Dual diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.710, Tmax = 1.000

  • 5171 measured reflections

  • 2613 independent reflections

  • 2489 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.079

  • S = 1.07

  • 2613 reflections

  • 185 parameters

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

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C10–C15 and N1,N2,C1,C6,C7 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O1i 0.88 (2) 2.14 (2) 2.9104 (16) 144.9 (19)
N2—H2⋯S1i 0.88 (2) 2.69 (2) 3.4073 (12) 139.1 (16)
C8—H8a⋯Cg1ii 0.99 2.89 3.5678 (15) 126
C8—H8b⋯Cg2iii 0.99 2.76 3.4204 (16) 125
Symmetry codes: (i) [-x, y, -z+{\script{3\over 2}}]; (ii) [x, -y, z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, 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/S160053681103666X/ez2258sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103666X/ez2258Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103666X/ez2258Isup3.cml

checkCIF report


Comment top

The structural analysis of the title compound, (I), is motivated by recent studies into the biological potential of benzimidazoles (Al-Rashood & Abdel-Aziz, 2010; Abdel-Aziz et al., 2010). The molecule of (I), Fig. 1, has a twisted V-shape. As expected, the benzimidazole residue is planar (r.m.s. deviation = 0.014 Å). The ketone group is co-planar with the benzene ring to which it is attached as seen in the value of the O1—C9—C10—C11 torsion angle of -173.18 (14) °. As the S1—C8—C9—O1 torsion angle is -0.39 (18) °, the molecule comprises two planar residues that form a dihedral angle of 82.4 (2) °. The most closely related structure in the literature is that of 2-(benzoylmethylsulfanyl)-6-methoxy-1H-benzimidazole (Lynch & McClenaghan, 2004), i.e. with a methoxy substituent on the benzene ring of the benzimidazole and no substituent on the ring attached to the ketone. This adopts a similar conformation with the ketone benzene ring inclined to the benzimidazole residue with the dihedral angle formed between the ring systems being 67.13 (9) °.

In the crystal packing two molecules, related by a 2-fold axis of symmetry associate via N—H···O and N—H···S hydrogen bonds as the amine-H atom is bifurcated, Table 1. As seen from Fig. 2, this results in the formation of two S(5), {···H···OC2S} ring motifs which flank a central eight-membered {···HNCS}2 synthon. The dimeric aggregates are linked into a supramolecular chain along the c axis via C—H···π interactions Table 1 and Fig. 3. Chains assemble into layers in the ab plane and are connected along the c axis via weak π···π interactions of 3.9578 (8) Å formed between the chloro-substituted benzene rings (C10–C15); symmetry operation: 1/2 - x, 1/2 - y, 1 - z, Fig. 4.

Related literature top

For the biological and pharmacological properties of benzimidazoles, see: Al-Rashood & Abdel-Aziz (2010); Abdel-Aziz et al. (2010). For the synthesis, see: Sarhan et al. (1996). For a related structure, see: Lynch & McClenaghan (2004).

Experimental top

The reaction of 2-mercaptobenzimidazole with 4-chloroacetophenone in boiling AcOH/H2SO4 afforded the sulfate salt of 2-(1H-benzo[d]imidazol-2-ylthio)-1-(4-chlorophenyl)ethanone after Sarhan et al. (1996). Neutralization of the latter salt afforded the title compound and the light-brown crystals were grown from its ethanol solution by slow evaporation at room temperature.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.99 Å, Uiso(H) = 1.2Ueq(C)] and were included in the refinement in the riding model approximation. The amino-H atom was located in a difference Fourier map, and subsequently refined freely.

Structure description top

The structural analysis of the title compound, (I), is motivated by recent studies into the biological potential of benzimidazoles (Al-Rashood & Abdel-Aziz, 2010; Abdel-Aziz et al., 2010). The molecule of (I), Fig. 1, has a twisted V-shape. As expected, the benzimidazole residue is planar (r.m.s. deviation = 0.014 Å). The ketone group is co-planar with the benzene ring to which it is attached as seen in the value of the O1—C9—C10—C11 torsion angle of -173.18 (14) °. As the S1—C8—C9—O1 torsion angle is -0.39 (18) °, the molecule comprises two planar residues that form a dihedral angle of 82.4 (2) °. The most closely related structure in the literature is that of 2-(benzoylmethylsulfanyl)-6-methoxy-1H-benzimidazole (Lynch & McClenaghan, 2004), i.e. with a methoxy substituent on the benzene ring of the benzimidazole and no substituent on the ring attached to the ketone. This adopts a similar conformation with the ketone benzene ring inclined to the benzimidazole residue with the dihedral angle formed between the ring systems being 67.13 (9) °.

In the crystal packing two molecules, related by a 2-fold axis of symmetry associate via N—H···O and N—H···S hydrogen bonds as the amine-H atom is bifurcated, Table 1. As seen from Fig. 2, this results in the formation of two S(5), {···H···OC2S} ring motifs which flank a central eight-membered {···HNCS}2 synthon. The dimeric aggregates are linked into a supramolecular chain along the c axis via C—H···π interactions Table 1 and Fig. 3. Chains assemble into layers in the ab plane and are connected along the c axis via weak π···π interactions of 3.9578 (8) Å formed between the chloro-substituted benzene rings (C10–C15); symmetry operation: 1/2 - x, 1/2 - y, 1 - z, Fig. 4.

For the biological and pharmacological properties of benzimidazoles, see: Al-Rashood & Abdel-Aziz (2010); Abdel-Aziz et al. (2010). For the synthesis, see: Sarhan et al. (1996). For a related structure, see: Lynch & McClenaghan (2004).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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. Dimeric aggregates with 2-fold symmetry and sustained by N—H···O and N—H···S hydrogen bonds, shown as blue and orange dashed lines, respectively.
[Figure 3] Fig. 3. Supramolecular chain in (I) whereby the dimeric aggregates shown in Fig. 2 are connected by C—H···π interactions (purple dashed lines), The N—H···O and N—H···S hydrogen bonds are shown as blue and orange dashed lines, respectively.
[Figure 4] Fig. 4. A view in projection down the c axis of the unit-cell contents of (I). The N—H···O, N—H···S and C—H···π interactions are shown as blue, orange and purple dashed lines, respectively.
2-(1H-1,3-Benzodiazol-2-ylsulfanyl)-1-(4-chlorophenyl)ethanone top
Crystal data top
C15H11ClN2OSF(000) = 1248
Mr = 302.77Dx = 1.530 Mg m−3
Monoclinic, C2/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2ycCell parameters from 3792 reflections
a = 27.3765 (4) Åθ = 3.2–74.1°
b = 9.2784 (2) ŵ = 4.02 mm−1
c = 10.3630 (2) ÅT = 100 K
β = 93.087 (1)°Block, light-brown
V = 2628.49 (9) Å30.40 × 0.30 × 0.20 mm
Z = 8
Data collection top
Agilent SuperNova Dual
diffractometer with Atlas detector		2613 independent reflections
Radiation source: SuperNova (Cu) X-ray Source2489 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.016
Detector resolution: 10.4041 pixels mm-1θmax = 74.2°, θmin = 3.2°
ω scanh = −32→34
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)		k = −11→10
Tmin = 0.710, Tmax = 1.000l = −9→12
5171 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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0442P)2 + 2.8814P]
where P = (Fo2 + 2Fc2)/3
2613 reflections(Δ/σ)max = 0.001
185 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C15H11ClN2OSV = 2628.49 (9) Å3
Mr = 302.77Z = 8
Monoclinic, C2/cCu Kα radiation
a = 27.3765 (4) ŵ = 4.02 mm−1
b = 9.2784 (2) ÅT = 100 K
c = 10.3630 (2) Å0.40 × 0.30 × 0.20 mm
β = 93.087 (1)°
Data collection top
Agilent SuperNova Dual
diffractometer with Atlas detector		2613 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)		2489 reflections with I > 2σ(I)
Tmin = 0.710, Tmax = 1.000Rint = 0.016
5171 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.30 e Å−3
2613 reflectionsΔρmin = −0.40 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*/Ueq
Cl10.282969 (13)0.21419 (4)0.22654 (4)0.01886 (12)
S10.059988 (12)−0.01719 (4)0.74205 (3)0.01091 (11)
O10.07341 (4)0.18383 (12)0.52818 (10)0.0138 (2)
N10.10732 (4)0.20841 (14)0.86384 (12)0.0121 (3)
N20.03011 (4)0.17240 (14)0.92176 (12)0.0118 (3)
H2−0.0005 (8)0.142 (2)0.9163 (19)0.026 (5)*
C10.09605 (5)0.30740 (16)0.95916 (13)0.0111 (3)
C20.12521 (5)0.41479 (17)1.01856 (14)0.0147 (3)
H2A0.15760.43150.99370.018*
C30.10522 (6)0.49602 (17)1.11487 (15)0.0156 (3)
H30.12440.56921.15700.019*
C40.05726 (6)0.47245 (17)1.15152 (15)0.0159 (3)
H40.04480.52991.21810.019*
C50.02753 (5)0.36737 (17)1.09304 (14)0.0141 (3)
H5−0.00500.35171.11730.017*
C60.04807 (5)0.28607 (15)0.99671 (13)0.0109 (3)
C70.06706 (5)0.13180 (16)0.84568 (13)0.0106 (3)
C80.11504 (5)0.00291 (16)0.65706 (14)0.0115 (3)
H8A0.14210.02950.71960.014*
H8B0.1233−0.09090.61840.014*
C90.11099 (5)0.11594 (15)0.55116 (13)0.0109 (3)
C100.15473 (5)0.13996 (16)0.47401 (13)0.0109 (3)
C110.19656 (5)0.05349 (17)0.48894 (14)0.0142 (3)
H110.1980−0.02110.55180.017*
C120.23593 (5)0.07600 (17)0.41252 (15)0.0153 (3)
H120.26420.01680.42220.018*
C130.23353 (5)0.18575 (17)0.32202 (14)0.0133 (3)
C140.19256 (5)0.27407 (16)0.30626 (14)0.0145 (3)
H140.19160.34980.24450.017*
C150.15315 (5)0.25001 (17)0.38202 (14)0.0129 (3)
H150.12480.30890.37130.015*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01085 (18)0.0243 (2)0.0221 (2)0.00010 (14)0.00726 (14)0.00128 (14)
S10.00850 (18)0.01265 (19)0.01167 (18)−0.00049 (12)0.00121 (12)−0.00085 (12)
O10.0078 (5)0.0169 (5)0.0168 (5)0.0032 (4)0.0010 (4)0.0014 (4)
N10.0084 (6)0.0141 (6)0.0138 (6)0.0000 (5)0.0005 (4)0.0004 (5)
N20.0071 (6)0.0149 (6)0.0134 (6)−0.0017 (5)0.0011 (4)−0.0022 (5)
C10.0088 (6)0.0125 (7)0.0120 (6)0.0005 (5)−0.0011 (5)0.0026 (5)
C20.0099 (6)0.0154 (7)0.0184 (7)−0.0025 (6)−0.0017 (5)0.0021 (6)
C30.0151 (7)0.0125 (7)0.0185 (7)−0.0023 (6)−0.0054 (6)0.0001 (6)
C40.0176 (7)0.0147 (7)0.0152 (7)0.0019 (6)−0.0008 (6)−0.0019 (6)
C50.0113 (7)0.0162 (7)0.0150 (7)0.0004 (6)0.0018 (5)−0.0008 (6)
C60.0096 (6)0.0110 (7)0.0118 (6)−0.0004 (5)−0.0019 (5)0.0009 (5)
C70.0084 (6)0.0131 (7)0.0101 (6)0.0009 (5)−0.0004 (5)0.0018 (5)
C80.0080 (6)0.0146 (7)0.0120 (6)0.0016 (5)0.0017 (5)−0.0004 (5)
C90.0097 (7)0.0111 (7)0.0118 (6)0.0001 (5)−0.0006 (5)−0.0038 (5)
C100.0076 (6)0.0130 (7)0.0122 (6)−0.0005 (5)−0.0007 (5)−0.0032 (5)
C110.0112 (7)0.0156 (7)0.0158 (7)0.0026 (6)0.0007 (5)0.0016 (6)
C120.0090 (7)0.0173 (8)0.0195 (7)0.0037 (6)0.0004 (5)−0.0002 (6)
C130.0081 (6)0.0176 (7)0.0143 (7)−0.0025 (6)0.0025 (5)−0.0037 (6)
C140.0123 (7)0.0143 (7)0.0168 (7)−0.0006 (6)0.0000 (6)0.0013 (6)
C150.0086 (6)0.0138 (7)0.0162 (7)0.0018 (6)−0.0012 (5)−0.0008 (6)
Geometric parameters (Å, º) top
Cl1—C131.7392 (15)C5—C61.394 (2)
S1—C71.7548 (15)C5—H50.9500
S1—C81.7958 (14)C8—C91.518 (2)
O1—C91.2187 (17)C8—H8A0.9900
N1—C71.3165 (19)C8—H8B0.9900
N1—C11.3955 (19)C9—C101.4920 (19)
N2—C71.3685 (18)C10—C151.396 (2)
N2—C61.3843 (19)C10—C111.400 (2)
N2—H20.88 (2)C11—C121.387 (2)
C1—C21.399 (2)C11—H110.9500
C1—C61.404 (2)C12—C131.384 (2)
C2—C31.386 (2)C12—H120.9500
C2—H2A0.9500C13—C141.392 (2)
C3—C41.403 (2)C14—C151.386 (2)
C3—H30.9500C14—H140.9500
C4—C51.388 (2)C15—H150.9500
C4—H40.9500
C7—S1—C898.65 (7)C9—C8—H8A108.9
C7—N1—C1103.95 (12)S1—C8—H8A108.9
C7—N2—C6106.36 (12)C9—C8—H8B108.9
C7—N2—H2127.0 (14)S1—C8—H8B108.9
C6—N2—H2126.0 (14)H8A—C8—H8B107.7
N1—C1—C2129.61 (13)O1—C9—C10120.76 (13)
N1—C1—C6110.45 (12)O1—C9—C8121.77 (13)
C2—C1—C6119.92 (13)C10—C9—C8117.46 (12)
C3—C2—C1117.78 (14)C15—C10—C11119.33 (13)
C3—C2—H2A121.1C15—C10—C9118.61 (13)
C1—C2—H2A121.1C11—C10—C9122.04 (13)
C2—C3—C4121.42 (14)C12—C11—C10120.44 (14)
C2—C3—H3119.3C12—C11—H11119.8
C4—C3—H3119.3C10—C11—H11119.8
C5—C4—C3121.76 (14)C11—C12—C13119.20 (14)
C5—C4—H4119.1C11—C12—H12120.4
C3—C4—H4119.1C13—C12—H12120.4
C4—C5—C6116.30 (13)C12—C13—C14121.44 (14)
C4—C5—H5121.8C12—C13—Cl1119.16 (11)
C6—C5—H5121.8C14—C13—Cl1119.40 (12)
N2—C6—C5132.02 (14)C15—C14—C13119.06 (14)
N2—C6—C1105.14 (12)C15—C14—H14120.5
C5—C6—C1122.81 (14)C13—C14—H14120.5
N1—C7—N2114.09 (13)C14—C15—C10120.53 (13)
N1—C7—S1125.23 (11)C14—C15—H15119.7
N2—C7—S1120.58 (11)C10—C15—H15119.7
C9—C8—S1113.32 (10)
C7—N1—C1—C2178.86 (15)C8—S1—C7—N1−11.63 (14)
C7—N1—C1—C60.28 (15)C8—S1—C7—N2172.27 (11)
N1—C1—C2—C3−177.76 (14)C7—S1—C8—C9−79.85 (11)
C6—C1—C2—C30.7 (2)S1—C8—C9—O1−0.39 (18)
C1—C2—C3—C4−0.4 (2)S1—C8—C9—C10−179.50 (10)
C2—C3—C4—C5−0.2 (2)O1—C9—C10—C155.2 (2)
C3—C4—C5—C60.4 (2)C8—C9—C10—C15−175.68 (13)
C7—N2—C6—C5−178.12 (15)O1—C9—C10—C11−173.18 (14)
C7—N2—C6—C10.27 (15)C8—C9—C10—C115.9 (2)
C4—C5—C6—N2178.08 (15)C15—C10—C11—C12−0.5 (2)
C4—C5—C6—C1−0.1 (2)C9—C10—C11—C12177.87 (13)
N1—C1—C6—N2−0.35 (16)C10—C11—C12—C130.5 (2)
C2—C1—C6—N2−179.09 (13)C11—C12—C13—C140.1 (2)
N1—C1—C6—C5178.23 (13)C11—C12—C13—Cl1179.83 (12)
C2—C1—C6—C5−0.5 (2)C12—C13—C14—C15−0.8 (2)
C1—N1—C7—N2−0.10 (16)Cl1—C13—C14—C15179.50 (11)
C1—N1—C7—S1−176.42 (10)C13—C14—C15—C100.8 (2)
C6—N2—C7—N1−0.12 (17)C11—C10—C15—C14−0.2 (2)
C6—N2—C7—S1176.39 (10)C9—C10—C15—C14−178.60 (13)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C10–C15 and N1,N2,C1,C6,C7 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.88 (2)2.14 (2)2.9104 (16)144.9 (19)
N2—H2···S1i0.88 (2)2.69 (2)3.4073 (12)139.1 (16)
C8—H8a···Cg1ii0.992.893.5678 (15)126
C8—H8b···Cg2iii0.992.763.4204 (16)125
Symmetry codes: (i) −x, y, −z+3/2; (ii) x, −y, z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC15H11ClN2OS
Mr302.77
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)27.3765 (4), 9.2784 (2), 10.3630 (2)
β (°) 93.087 (1)
V (Å3)2628.49 (9)
Z8
Radiation typeCu Kα
µ (mm−1)4.02
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.710, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		5171, 2613, 2489
Rint0.016
(sin θ/λ)max (Å−1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.079, 1.07
No. of reflections2613
No. of parameters185
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.30, −0.40

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

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C10–C15 and N1,N2,C1,C6,C7 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.88 (2)2.14 (2)2.9104 (16)144.9 (19)
N2—H2···S1i0.88 (2)2.69 (2)3.4073 (12)139.1 (16)
C8—H8a···Cg1ii0.992.893.5678 (15)126
C8—H8b···Cg2iii0.992.763.4204 (16)125
Symmetry codes: (i) −x, y, −z+3/2; (ii) x, −y, z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.
 

Footnotes

‡Additional correspondence author, e-mail: hatem_741@yahoo.com.

Acknowledgements

The authors thank King Saud University and the University of Malaya for supporting this study.

References

First citationAbdel-Aziz, H. A., Saleh, T. S. & El-Zahabi, H. S. A. (2010). Arch. Pharm. 343, 24–30.  CAS Google Scholar
 First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
 First citationAl-Rashood, K. A. & Abdel-Aziz, H. A. (2010). Molecules, 15, 3775–3815.  Web of Science CAS 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 citationLynch, D. E. & McClenaghan, I. (2004). Acta Cryst. E60, o363–o364.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSarhan, A. A. O., El-Shereif, H. A. H. & Mahmoud, A. M. (1996). Tetrahedron, 52, 10485–10496.  CrossRef CAS Web of Science 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 67| Part 10| October 2011| Page o2639
https://doi.org/10.1107/S160053681103666X
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