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Acta Cryst. (2009). E65, o1245    [ doi:10.1107/S1600536809016481 ]

N-(Benzothiazol-2-yl)-3-chlorobenzamide

M. Khawar Rauf, M. Bolte and A. Badshah

Abstract top

The title molecule, C14H9ClN2OS, exists in the solid state in its amide form with a typical C=O bond length, as well as shortened C-N bonds. The plane containing the HNCO atoms subtends dihedral angles of 12.3 (4) and 8.1 (3)° with the planes of the phenyl ring and benzothiazole group, respectively, whereas the dihedral angle between the planes of the phenyl ring and the benzothiazole group is 5.96 (6)°. In the crystal, molecules form intermolecular N-H...N hydrogen bonds, generating independent scissor-like R22(8) dimers.

Comment top

We report here the structure of the title compound, (I) (Fig. 1), which has been separated from an impure sample of thiourea by column chromatography as a by-product, a part of our ongoing studies related to N,N'-disubstituted thioureas and heterocyclic compounds. These include N—H···N hydrogen bonds, with possible oxygen-sulfur intramolecular interactions (Fig. 2). In this class of componds, N—H···O, C—H···O and N—H···N hydrogen bonds, and weak π–π stacking interactions are the only direction-specific intermolecular interactions (Garden et al., 2005; Wardell et al., 2005). The molecules of (I) are nearly planar, as shown by the leading torsion angles [C11—C1—N1—C2 174.90 (12) and C1—N1—C2—N2 -171.57 (13)°], and the amide group adopts the usual trans conformation; the bond lengths and inter-bond angles present no unusual values (Allen et al., 1987).

Related literature top

For geometric data, see: Allen et al. (1987); For related structures, see: Garden et al. (2005); Wardell et al. (2005).

Experimental top

Freshly prepared and steam-distilled 3-chlorobenzoyl isothiocyanate (1.98 g, 10 mmol) was stirred in acetone (30 ml) for 20 min. Neat 2-aminobenzothiazole (1.50 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into 300 ml (approx.) acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water. One of the fraction obtained as a by-product during the column chromatography of the target thiourea was recrystallized from methanol/1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall fractional yield of 15%.

Refinement top

H atoms bonded to C were included in calculated positions and refined as riding on their parent C atom with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). The H atom bonded to N was freely refined.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I) with view onto the ac plane. Hydrogen bonds shown as dashed lines. H atoms are omitted for clarity.
N-(Benzothiazol-2-yl)-3-chlorobenzamide top
Crystal data top
C14H9ClN2OSF000 = 1184
Mr = 288.74Dx = 1.520 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8429 reflections
a = 26.6613 (19) Åθ = 3.6–25.9º
b = 7.5766 (5) ŵ = 0.46 mm−1
c = 12.6729 (10) ÅT = 173 K
β = 99.729 (6)ºBlock, light yellow
V = 2523.1 (3) Å30.39 × 0.38 × 0.35 mm
Z = 8
Data collection top
Stoe IPDS II two-circle
diffractometer		2352 independent reflections
Radiation source: fine-focus sealed tube2084 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
T = 173 Kθmax = 25.6º
ω scansθmin = 3.6º
Absorption correction: multi-scan
[MULABS (Spek, 2009); Blessing, 1995)]		h = −32→32
Tmin = 0.841, Tmax = 0.856k = −8→9
9132 measured reflectionsl = −15→15
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.028  w = 1/[σ2(Fo2) + (0.051P)2 + 0.8598P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.29 e Å−3
2352 reflectionsΔρmin = −0.22 e Å−3
177 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0071 (6)
Secondary atom site location: difference Fourier map
Crystal data top
C14H9ClN2OSV = 2523.1 (3) Å3
Mr = 288.74Z = 8
Monoclinic, C2/cMo Kα
a = 26.6613 (19) ŵ = 0.46 mm−1
b = 7.5766 (5) ÅT = 173 K
c = 12.6729 (10) Å0.39 × 0.38 × 0.35 mm
β = 99.729 (6)º
Data collection top
Stoe IPDS II two-circle
diffractometer		2352 independent reflections
Absorption correction: multi-scan
[MULABS (Spek, 2009); Blessing, 1995)]		2084 reflections with I > 2σ(I)
Tmin = 0.841, Tmax = 0.856Rint = 0.038
9132 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028177 parameters
wR(F2) = 0.079H atoms treated by a mixture of
independent and constrained refinement
S = 1.03Δρmax = 0.29 e Å−3
2352 reflectionsΔρmin = −0.22 e Å−3
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
Cl10.762196 (14)0.69837 (6)0.65336 (3)0.03053 (14)
S10.500738 (13)0.23662 (5)0.45176 (3)0.01915 (13)
O10.58693 (4)0.40431 (15)0.51591 (8)0.0241 (3)
N10.54529 (4)0.34541 (16)0.65241 (10)0.0178 (3)
H10.5448 (7)0.325 (2)0.7252 (17)0.032 (5)*
C10.58602 (5)0.41061 (19)0.61190 (11)0.0179 (3)
N20.46256 (4)0.23590 (16)0.62817 (10)0.0185 (3)
C20.50288 (5)0.27653 (19)0.58813 (11)0.0167 (3)
C30.42583 (5)0.16277 (19)0.54925 (12)0.0185 (3)
C40.44015 (5)0.15038 (19)0.44819 (12)0.0191 (3)
C50.40794 (6)0.0750 (2)0.36146 (12)0.0242 (3)
H50.41790.06610.29320.029*
C60.36121 (6)0.0141 (2)0.37817 (13)0.0275 (4)
H60.3388−0.03910.32070.033*
C70.34626 (6)0.0292 (2)0.47829 (13)0.0273 (4)
H70.3136−0.01180.48730.033*
C80.37807 (5)0.1024 (2)0.56412 (12)0.0234 (3)
H80.36770.11170.63200.028*
C110.62782 (5)0.49568 (19)0.68791 (11)0.0188 (3)
C120.67079 (5)0.5438 (2)0.64573 (12)0.0200 (3)
H120.67340.51400.57400.024*
C130.70955 (5)0.6348 (2)0.70855 (12)0.0213 (3)
C140.70650 (6)0.6824 (2)0.81238 (12)0.0245 (3)
H140.73330.74630.85470.029*
C150.66341 (6)0.6349 (2)0.85358 (12)0.0249 (3)
H150.66070.66720.92480.030*
C160.62434 (6)0.5413 (2)0.79260 (12)0.0220 (3)
H160.59530.50830.82220.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0200 (2)0.0423 (3)0.0307 (2)−0.00460 (15)0.00835 (16)0.00331 (17)
S10.0228 (2)0.0232 (2)0.0121 (2)0.00280 (14)0.00466 (14)0.00001 (13)
O10.0263 (6)0.0325 (6)0.0148 (6)−0.0019 (4)0.0074 (4)−0.0004 (4)
N10.0188 (6)0.0221 (7)0.0128 (6)0.0014 (5)0.0041 (5)0.0011 (5)
C10.0199 (7)0.0189 (7)0.0161 (8)0.0046 (5)0.0061 (5)0.0018 (5)
N20.0183 (6)0.0227 (7)0.0143 (6)0.0024 (5)0.0019 (5)0.0000 (5)
C20.0207 (7)0.0178 (7)0.0121 (7)0.0050 (5)0.0040 (5)0.0019 (5)
C30.0203 (7)0.0188 (7)0.0156 (7)0.0042 (6)0.0008 (5)0.0014 (5)
C40.0220 (7)0.0184 (7)0.0167 (7)0.0044 (6)0.0024 (6)0.0011 (6)
C50.0322 (8)0.0214 (8)0.0172 (8)0.0050 (6)−0.0009 (6)−0.0020 (6)
C60.0301 (8)0.0230 (8)0.0256 (9)0.0001 (6)−0.0060 (6)−0.0029 (6)
C70.0233 (8)0.0253 (9)0.0311 (9)−0.0005 (6)−0.0015 (6)0.0036 (7)
C80.0225 (7)0.0260 (9)0.0215 (8)0.0026 (6)0.0030 (6)0.0032 (6)
C110.0220 (7)0.0182 (7)0.0170 (7)0.0033 (6)0.0053 (6)0.0021 (6)
C120.0220 (7)0.0228 (8)0.0162 (7)0.0034 (6)0.0061 (6)0.0008 (6)
C130.0198 (7)0.0231 (8)0.0221 (8)0.0012 (6)0.0067 (6)0.0048 (6)
C140.0280 (8)0.0240 (8)0.0202 (8)−0.0027 (6)0.0004 (6)0.0010 (6)
C150.0337 (8)0.0259 (8)0.0159 (7)−0.0028 (7)0.0063 (6)0.0000 (6)
C160.0267 (8)0.0241 (8)0.0173 (8)−0.0004 (6)0.0095 (6)0.0027 (6)
Geometric parameters (Å, °) top
Cl1—C131.7386 (15)C6—C71.397 (2)
S1—C41.7360 (15)C6—H60.9500
S1—C21.7459 (14)C7—C81.378 (2)
O1—C11.2216 (18)C7—H70.9500
N1—C11.3696 (18)C8—H80.9500
N1—C21.3794 (18)C11—C161.389 (2)
N1—H10.94 (2)C11—C121.392 (2)
C1—C111.491 (2)C12—C131.378 (2)
N2—C21.3008 (19)C12—H120.9500
N2—C31.3912 (18)C13—C141.380 (2)
C3—C81.395 (2)C14—C151.388 (2)
C3—C41.400 (2)C14—H140.9500
C4—C51.397 (2)C15—C161.383 (2)
C5—C61.378 (2)C15—H150.9500
C5—H50.9500C16—H160.9500
C4—S1—C288.03 (7)C8—C7—H7119.4
C1—N1—C2122.53 (12)C6—C7—H7119.4
C1—N1—H1125.0 (11)C7—C8—C3118.64 (14)
C2—N1—H1111.8 (11)C7—C8—H8120.7
O1—C1—N1120.63 (13)C3—C8—H8120.7
O1—C1—C11121.46 (13)C16—C11—C12119.59 (14)
N1—C1—C11117.86 (12)C16—C11—C1124.15 (13)
C2—N2—C3109.98 (12)C12—C11—C1116.03 (12)
N2—C2—N1120.53 (13)C13—C12—C11119.64 (13)
N2—C2—S1117.01 (11)C13—C12—H12120.2
N1—C2—S1122.45 (11)C11—C12—H12120.2
N2—C3—C8125.53 (13)C12—C13—C14121.49 (14)
N2—C3—C4114.62 (13)C12—C13—Cl1118.93 (12)
C8—C3—C4119.85 (14)C14—C13—Cl1119.52 (12)
C5—C4—C3121.38 (14)C13—C14—C15118.48 (14)
C5—C4—S1128.30 (12)C13—C14—H14120.8
C3—C4—S1110.32 (11)C15—C14—H14120.8
C6—C5—C4117.87 (15)C16—C15—C14121.08 (14)
C6—C5—H5121.1C16—C15—H15119.5
C4—C5—H5121.1C14—C15—H15119.5
C5—C6—C7121.06 (14)C15—C16—C11119.71 (13)
C5—C6—H6119.5C15—C16—H16120.1
C7—C6—H6119.5C11—C16—H16120.1
C8—C7—C6121.19 (15)
C2—N1—C1—O1−2.6 (2)C5—C6—C7—C8−1.2 (2)
C2—N1—C1—C11174.90 (12)C6—C7—C8—C30.3 (2)
C3—N2—C2—N1−177.62 (12)N2—C3—C8—C7−178.45 (14)
C3—N2—C2—S11.43 (16)C4—C3—C8—C70.9 (2)
C1—N1—C2—N2−171.57 (13)O1—C1—C11—C16165.51 (14)
C1—N1—C2—S19.43 (19)N1—C1—C11—C16−11.9 (2)
C4—S1—C2—N2−1.80 (12)O1—C1—C11—C12−8.9 (2)
C4—S1—C2—N1177.23 (12)N1—C1—C11—C12173.61 (12)
C2—N2—C3—C8179.29 (14)C16—C11—C12—C130.5 (2)
C2—N2—C3—C4−0.12 (18)C1—C11—C12—C13175.22 (13)
N2—C3—C4—C5178.08 (13)C11—C12—C13—C14−1.1 (2)
C8—C3—C4—C5−1.4 (2)C11—C12—C13—Cl1−178.45 (11)
N2—C3—C4—S1−1.19 (16)C12—C13—C14—C150.7 (2)
C8—C3—C4—S1179.37 (11)Cl1—C13—C14—C15178.04 (12)
C2—S1—C4—C5−177.64 (15)C13—C14—C15—C160.3 (2)
C2—S1—C4—C31.56 (11)C14—C15—C16—C11−0.8 (2)
C3—C4—C5—C60.5 (2)C12—C11—C16—C150.4 (2)
S1—C4—C5—C6179.62 (12)C1—C11—C16—C15−173.83 (14)
C4—C5—C6—C70.8 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.94 (2)2.02 (2)2.9429 (18)168.9 (17)
Symmetry codes: (i) −x+1, y, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.94 (2)2.02 (2)2.9429 (18)168.9 (17)
Symmetry codes: (i) −x+1, y, −z+3/2.
Acknowledgements top

MKR is grateful to the HEC, Pakistan, for financial support of the PhD program under scholarship No. ILC-0363104.

references
References top

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.

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Garden, S. J., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o450–o451.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.

Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o634–o638.