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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 o2612
https://doi.org/10.1107/S1600536811035549

N′-[(E)-2-Chloro­benzyl­­idene]-2-[(1,3,4-thia­diazol-2-yl)sulfan­yl]acetohydrazide

S. Mohan,a‡ S. Ananthan,b P. Ramesh,c D. Saravanand and M. N. Ponnuswamyc*

aResearch and Development Centre, Orchid Chemicals and Pharmaceuticals Ltd, Chennai 600 119, India, bDepartment of Chemistry, Presidency College (Autonomous), Chennai 600 005, India, cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and dDepartment of Chemistry, National College, Tiruchirappali 620 001, India
*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 25 July 2011; accepted 31 August 2011; online 14 September 2011)

In the title compound, C11H9ClN4OS2, the thia­diazole and chloro­phenyl rings are oriented at an angle of 43.1 (1)°. The sum of the bond angles around the amide N atom (359.8°) of the acetohydrazide group is in accordance with a model of sp2 hybridization. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R22(8) loops. Weak C—H⋯π inter­actions also occur.

Related literature

For related literature on the biological activities of 1,3,4-thiadia­zole derivatives, see: Alireza et al. (2005[Alireza, F., Saeed, E., Abdolreza, H., Majid, R., Kazem, S., Mohammad, H. M. & Abbas, S. (2005). Bioorg. Med. Chem. Lett. 15, S4488-S4492.]); Matysiak & Opolski (2006[Matysiak, J. & Opolski, A. (2006). Bioorg. Med. Chem. 14, 4483-4489.]); Wang et al. (1999[Wang, Y. G., Cao, L., Yan, J., Ye, W. F., Zhou, Q. C. & Lu, B. X. (1999). Chem. J. Chin. Univ. 20, S1903-S1905.]). 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.]).

[Scheme 1]

Experimental

Crystal data

  • C11H9ClN4OS2

  • Mr = 312.79

  • Triclinic, [P \overline 1]

  • a = 7.551 (5) Å

  • b = 8.743 (3) Å

  • c = 11.269 (5) Å

  • α = 69.295 (5)°

  • β = 87.493 (4)°

  • γ = 78.892 (5)°

  • V = 682.6 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.58 mm−1

  • T = 293 K

  • 0.20 × 0.17 × 0.16 mm
Data collection

  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.911

  • 12836 measured reflections

  • 3446 independent reflections

  • 2858 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.121

  • S = 1.05

  • 3446 reflections

  • 176 parameters

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

  • Δρmax = 0.81 e Å−3

  • Δρmin = −0.70 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1/N2/N3/C4 ring.

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N7—H7⋯O1i 0.91 (3) 1.93 (3) 2.845 (3) 175 (2)
C5—H5A⋯Cg1ii 0.97 2.95 3.896(3) 165
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035549/bt5593sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035549/bt5593Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035549/bt5593Isup3.cml

checkCIF report


Comment top

1,3,4-Thiadiazole derivatives are of interest because of their chemical and pharmaceutical properties. Some derivatives are useful in the preparation of intermediate for anticarcinogens. Recently many 1,3,4- thiadiazole nucleus have been synthesized and evaluated for their antiproliferative effect in vitro against the cells of various human tumor cell lines (Matysiak & Opolski, 2006). Some of the derivatives have effective antibacterial (Alireza et al., 2005) and insecticidal activities (Wang et al., 1999). In view of these facts and to ascertain the molecular conformation, crystallographic study of the title compound has been carried out.

The ORTEP plot of the molecule is shown in Fig.1. The thiadiazole and the chlorophenyl rings are planar and oriented at an angle of 43.1 (1)° with each other. The sum of the bond angles around the N7 atom (359.8°) of the acetohydrazide group in the molecule is in accordance with sp2 hybridization. The packing of the molecules are controlled by N—H···O, C—H···Cl, C—H···π, π···π types of intra and intermolecular interactions. Atom N7 of the molecule at (x, y, z) donates a proton to atom O1 of the molecule at (2 - x, 1 - y, 1 - z) forming an intermolecular N—H···O bond which link the molecules into R22(8) dimer (Bernstein et al., 1995) as shown in Fig 2. The acetohydrazide group interacts with the thiadiazole ring moiety through a C—H···π interaction involving atom C5, the separation between H5A and the centroid of the S1/C1/N2/N3/C4 (Cg1) ring being 2.95 Å.

Related literature top

For related literature on the biological activities of 1,3,4-thiazole derivatives, see: Alireza et al. (2005); Matysiak & Opolski (2006); Wang et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a solution of 2-mercaptothiadiazole (50 g; 423 mmol) in acetone (500 ml) anhydrous sodium carbonate (24.66 g; 233 mmol) was added. Ethyl bromoacetate (70.65 g; 423 mmol) was added slowly to the reaction mixture at room temperature under stirring. The progress of the reaction was monitored by thin layer chromatography using ethyl acetate/n-hexane (3:7) as eluent. The bye-product sodium bromide was removed by filtration. The mother liquor was concentrated under vacuum to remove acetone and the residual acetone was removed by strip off with methanol to yield ethyl (1,3,4- thiadiazol-2-ylthio)acetate. The residue was dissolved in methanol (300 ml) and the clear solution hydrazine hydrate (42.35 g; 846 mmol) was added and heated under reflux. The progress of the reaction was monitored by thin layer chromatography using chloroform/methanol (9:1) as eluent. The reaction mass was cooled to 0–5° C. The crystallized product, 2-(1,3,4- thiadiazol-2-ylthio)acetohydrazide was filtered and washed with chilled methanol. To a mixture of isolated product (10 mmol) and 2-chlorobenzaldehyde (10 mmol) in ethanol (20 ml), a few drops of acetic acid was added. The reaction mixture was heated under reflux till completion of reaction. The reaction was monitored by thin layer chromatography using chloroform /methanol (8:2). The reaction mass was cooled to room temperature. The crystallized product, 2-[1,3,4-Thiadiazol-2-ylthio]-N'-[(1E) -(2-chlorophenyl)methylene]acetohydrazide was filtered and washed with ethanol.

Refinement top

The N bound H atom was refined and the C bound H atoms positioned geometrically (C—H=0.93–0.97 Å) and allowed to ride on their parent atoms, with 1.2 Ueq(C) for all H atoms.

Structure description top

1,3,4-Thiadiazole derivatives are of interest because of their chemical and pharmaceutical properties. Some derivatives are useful in the preparation of intermediate for anticarcinogens. Recently many 1,3,4- thiadiazole nucleus have been synthesized and evaluated for their antiproliferative effect in vitro against the cells of various human tumor cell lines (Matysiak & Opolski, 2006). Some of the derivatives have effective antibacterial (Alireza et al., 2005) and insecticidal activities (Wang et al., 1999). In view of these facts and to ascertain the molecular conformation, crystallographic study of the title compound has been carried out.

The ORTEP plot of the molecule is shown in Fig.1. The thiadiazole and the chlorophenyl rings are planar and oriented at an angle of 43.1 (1)° with each other. The sum of the bond angles around the N7 atom (359.8°) of the acetohydrazide group in the molecule is in accordance with sp2 hybridization. The packing of the molecules are controlled by N—H···O, C—H···Cl, C—H···π, π···π types of intra and intermolecular interactions. Atom N7 of the molecule at (x, y, z) donates a proton to atom O1 of the molecule at (2 - x, 1 - y, 1 - z) forming an intermolecular N—H···O bond which link the molecules into R22(8) dimer (Bernstein et al., 1995) as shown in Fig 2. The acetohydrazide group interacts with the thiadiazole ring moiety through a C—H···π interaction involving atom C5, the separation between H5A and the centroid of the S1/C1/N2/N3/C4 (Cg1) ring being 2.95 Å.

For related literature on the biological activities of 1,3,4-thiazole derivatives, see: Alireza et al. (2005); Matysiak & Opolski (2006); Wang et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Perspective view of the molecule showing the thermal ellipsoids are drawn at 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the molecules viewed down b–axis. H atoms not involved in hydrogen bonding have been omitted for clarity.
N'-[(E)-2-Chlorobenzylidene]-2-[(1,3,4-thiadiazol-2- yl)sulfanyl]acetohydrazide top
Crystal data top
C11H9ClN4OS2Z = 2
Mr = 312.79F(000) = 320
Triclinic, P1Dx = 1.522 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.551 (5) ÅCell parameters from 1536 reflections
b = 8.743 (3) Åθ = 1.9–28.6°
c = 11.269 (5) ŵ = 0.58 mm−1
α = 69.295 (5)°T = 293 K
β = 87.493 (4)°Block, colorless
γ = 78.892 (5)°0.20 × 0.17 × 0.16 mm
V = 682.6 (6) Å3
Data collection top
Bruker SMART APEXII area-detector
diffractometer		3446 independent reflections
Radiation source: fine-focus sealed tube2858 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω and φ scansθmax = 28.6°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −10→10
Tmin = 0.890, Tmax = 0.911k = −11→11
12836 measured reflectionsl = −15→15
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0552P)2 + 0.298P]
where P = (Fo2 + 2Fc2)/3
3446 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.81 e Å−3
0 restraintsΔρmin = −0.70 e Å−3
Crystal data top
C11H9ClN4OS2γ = 78.892 (5)°
Mr = 312.79V = 682.6 (6) Å3
Triclinic, P1Z = 2
a = 7.551 (5) ÅMo Kα radiation
b = 8.743 (3) ŵ = 0.58 mm−1
c = 11.269 (5) ÅT = 293 K
α = 69.295 (5)°0.20 × 0.17 × 0.16 mm
β = 87.493 (4)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer		3446 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		2858 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.911Rint = 0.026
12836 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.81 e Å−3
3446 reflectionsΔρmin = −0.70 e Å−3
176 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
S10.25535 (9)0.03479 (8)0.74213 (5)0.06663 (19)
S20.56742 (7)0.20903 (7)0.65247 (4)0.05462 (16)
Cl10.84070 (13)0.88994 (8)−0.05412 (6)0.0894 (3)
O10.8486 (2)0.3817 (2)0.59757 (12)0.0554 (3)
C10.1207 (3)0.0256 (3)0.6276 (2)0.0626 (5)
H10.0209−0.02580.64690.075*
N20.1673 (3)0.0946 (3)0.51348 (18)0.0629 (5)
N30.3200 (3)0.1628 (2)0.50782 (16)0.0562 (4)
C40.3807 (3)0.1407 (2)0.61968 (17)0.0463 (4)
C50.6334 (3)0.3041 (2)0.49114 (16)0.0471 (4)
H5A0.67000.22030.45240.057*
H5B0.53330.38570.44140.057*
C60.7884 (2)0.3867 (2)0.49625 (16)0.0438 (4)
N70.8544 (2)0.4699 (2)0.38490 (14)0.0489 (4)
H70.950 (3)0.519 (3)0.386 (2)0.065 (7)*
N80.7873 (2)0.4676 (2)0.27372 (13)0.0460 (3)
C90.8396 (2)0.5689 (2)0.17253 (16)0.0449 (4)
H90.91130.64200.17730.054*
C100.7866 (2)0.5701 (2)0.04874 (16)0.0454 (4)
C110.7840 (3)0.7090 (3)−0.06154 (18)0.0556 (5)
C120.7388 (3)0.7078 (3)−0.17847 (19)0.0672 (6)
H120.73700.8021−0.25070.081*
C130.6966 (3)0.5678 (4)−0.1873 (2)0.0729 (7)
H130.66670.5665−0.26610.087*
C140.6980 (3)0.4283 (4)−0.0810 (2)0.0694 (6)
H140.66920.3330−0.08800.083*
C150.7423 (3)0.4294 (3)0.0368 (2)0.0562 (5)
H150.74220.33480.10850.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0858 (4)0.0739 (4)0.0431 (3)−0.0386 (3)0.0118 (3)−0.0131 (2)
S20.0671 (3)0.0632 (3)0.0327 (2)−0.0252 (2)−0.00281 (19)−0.0087 (2)
Cl10.1404 (7)0.0620 (4)0.0558 (3)−0.0234 (4)−0.0051 (4)−0.0055 (3)
O10.0617 (8)0.0749 (9)0.0336 (6)−0.0256 (7)−0.0014 (5)−0.0173 (6)
C10.0675 (13)0.0632 (13)0.0646 (13)−0.0273 (11)0.0083 (10)−0.0247 (10)
N20.0700 (11)0.0703 (12)0.0560 (10)−0.0295 (9)0.0011 (8)−0.0228 (9)
N30.0681 (11)0.0625 (10)0.0417 (8)−0.0259 (8)0.0007 (7)−0.0155 (7)
C40.0587 (11)0.0410 (8)0.0378 (8)−0.0138 (8)0.0045 (7)−0.0102 (7)
C50.0586 (11)0.0522 (10)0.0329 (8)−0.0178 (8)0.0016 (7)−0.0140 (7)
C60.0475 (9)0.0489 (9)0.0345 (8)−0.0097 (7)−0.0018 (7)−0.0134 (7)
N70.0493 (9)0.0647 (10)0.0330 (7)−0.0199 (8)−0.0038 (6)−0.0125 (7)
N80.0448 (8)0.0608 (9)0.0320 (7)−0.0129 (7)−0.0030 (6)−0.0138 (6)
C90.0429 (9)0.0537 (10)0.0365 (8)−0.0108 (7)−0.0017 (7)−0.0126 (7)
C100.0395 (8)0.0597 (11)0.0341 (8)−0.0061 (7)0.0009 (6)−0.0148 (7)
C110.0578 (11)0.0646 (12)0.0369 (9)−0.0040 (9)−0.0001 (8)−0.0127 (8)
C120.0677 (14)0.0887 (17)0.0342 (9)−0.0003 (12)−0.0031 (9)−0.0154 (10)
C130.0602 (13)0.118 (2)0.0442 (11)−0.0046 (13)−0.0054 (9)−0.0385 (13)
C140.0605 (13)0.0982 (18)0.0666 (14)−0.0197 (12)0.0004 (11)−0.0470 (14)
C150.0530 (11)0.0702 (13)0.0489 (10)−0.0155 (9)0.0012 (8)−0.0230 (9)
Geometric parameters (Å, º) top
S1—C11.711 (3)N7—H70.91 (3)
S1—C41.725 (2)N8—C91.273 (2)
S2—C41.734 (2)C9—C101.464 (2)
S2—C51.8044 (19)C9—H90.9300
Cl1—C111.747 (3)C10—C151.387 (3)
O1—C61.231 (2)C10—C111.394 (3)
C1—N21.278 (3)C11—C121.380 (3)
C1—H10.9300C12—C131.360 (4)
N2—N31.386 (3)C12—H120.9300
N3—C41.296 (2)C13—C141.373 (4)
C5—C61.502 (3)C13—H130.9300
C5—H5A0.9700C14—C151.387 (3)
C5—H5B0.9700C14—H140.9300
C6—N71.338 (2)C15—H150.9300
N7—N81.380 (2)
C1—S1—C486.64 (11)C9—N8—N7115.02 (16)
C4—S2—C597.92 (9)N8—C9—C10119.93 (17)
N2—C1—S1115.12 (18)N8—C9—H9120.0
N2—C1—H1122.4C10—C9—H9120.0
S1—C1—H1122.4C15—C10—C11117.46 (18)
C1—N2—N3112.27 (18)C15—C10—C9120.55 (17)
C4—N3—N2112.06 (17)C11—C10—C9121.96 (19)
N3—C4—S1113.92 (16)C12—C11—C10121.7 (2)
N3—C4—S2126.04 (15)C12—C11—Cl1118.25 (18)
S1—C4—S2120.04 (11)C10—C11—Cl1120.05 (16)
C6—C5—S2107.09 (12)C13—C12—C11119.5 (2)
C6—C5—H5A110.3C13—C12—H12120.2
S2—C5—H5A110.3C11—C12—H12120.2
C6—C5—H5B110.3C12—C13—C14120.6 (2)
S2—C5—H5B110.3C12—C13—H13119.7
H5A—C5—H5B108.6C14—C13—H13119.7
O1—C6—N7121.70 (17)C13—C14—C15120.0 (2)
O1—C6—C5121.66 (16)C13—C14—H14120.0
N7—C6—C5116.62 (15)C15—C14—H14120.0
C6—N7—N8119.89 (16)C10—C15—C14120.7 (2)
C6—N7—H7118.1 (16)C10—C15—H15119.6
N8—N7—H7121.8 (16)C14—C15—H15119.6
C4—S1—C1—N2−0.2 (2)N7—N8—C9—C10176.09 (16)
S1—C1—N2—N30.1 (3)N8—C9—C10—C15−24.7 (3)
C1—N2—N3—C40.1 (3)N8—C9—C10—C11157.42 (19)
N2—N3—C4—S1−0.3 (2)C15—C10—C11—C120.2 (3)
N2—N3—C4—S2−179.38 (15)C9—C10—C11—C12178.18 (19)
C1—S1—C4—N30.26 (17)C15—C10—C11—Cl1−179.30 (15)
C1—S1—C4—S2179.43 (14)C9—C10—C11—Cl1−1.3 (3)
C5—S2—C4—N3−1.1 (2)C10—C11—C12—C13−0.5 (3)
C5—S2—C4—S1179.81 (12)Cl1—C11—C12—C13179.03 (18)
C4—S2—C5—C6175.22 (13)C11—C12—C13—C140.3 (4)
S2—C5—C6—O10.3 (2)C12—C13—C14—C150.1 (4)
S2—C5—C6—N7−177.98 (14)C11—C10—C15—C140.2 (3)
O1—C6—N7—N8177.73 (17)C9—C10—C15—C14−177.78 (19)
C5—C6—N7—N8−4.0 (3)C13—C14—C15—C10−0.4 (3)
C6—N7—N8—C9170.33 (17)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the S1/C1/N2/N3/C4 ring.
D—H···AD—HH···AD···AD—H···A
C9—H9···Cl10.932.733.056 (2)102
N7—H7···O1i0.91 (3)1.93 (3)2.845 (3)175 (2)
C5—H5A···Cg1ii0.972.953.896 (3)165
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC11H9ClN4OS2
Mr312.79
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.551 (5), 8.743 (3), 11.269 (5)
α, β, γ (°)69.295 (5), 87.493 (4), 78.892 (5)
V (Å3)682.6 (6)
Z2
Radiation typeMo Kα
µ (mm−1)0.58
Crystal size (mm)0.20 × 0.17 × 0.16
Data collection
DiffractometerBruker SMART APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.890, 0.911
No. of measured, independent and
observed [I > 2σ(I)] reflections		12836, 3446, 2858
Rint0.026
(sin θ/λ)max (Å−1)0.674
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.121, 1.05
No. of reflections3446
No. of parameters176
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.81, −0.70

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the S1/C1/N2/N3/C4 ring.
D—H···AD—HH···AD···AD—H···A
C9—H9···Cl10.932.733.056 (2)101.5
N7—H7···O1i0.91 (3)1.93 (3)2.845 (3)175 (2)
C5—H5A···Cg1ii0.972.953.896 (3)165
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1.
 

Footnotes

‡Parent department: Department of Chemistry, Presidency College (Autonomous), Chennai 600 005, India.

Acknowledgements

The authors thank the GNR X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection.

References

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Volume 67| Part 10| October 2011| Page o2612
https://doi.org/10.1107/S1600536811035549
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