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

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ISSN: 2056-9890

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

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and cDepartment of Chemistry, Islamia University of Bahawalpur, Pakistan
*Correspondence e-mail: aminbadshah@yahoo.com

(Received 29 April 2009; accepted 2 May 2009; online 14 May 2009)

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.

Related literature

For geometric 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 related structures, see: Garden et al. (2005[Garden, S. J., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o450-o451.]); Wardell et al. (2005[Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o634-o638.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9ClN2OS

  • Mr = 288.74

  • Monoclinic, C 2/c

  • a = 26.6613 (19) Å

  • b = 7.5766 (5) Å

  • c = 12.6729 (10) Å

  • β = 99.729 (6)°

  • V = 2523.1 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.46 mm−1

  • T = 173 K

  • 0.39 × 0.38 × 0.35 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan [MULABS (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.])] Tmin = 0.841, Tmax = 0.856

  • 9132 measured reflections

  • 2352 independent reflections

  • 2084 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.079

  • S = 1.03

  • 2352 reflections

  • 177 parameters

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

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯N2i 0.94 (2) 2.02 (2) 2.9429 (18) 168.9 (17)
Symmetry code: (i) [-x+1, y, -z+{\script{3\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 ππ 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
C14H9ClN2OSF(000) = 1184
Mr = 288.74Dx = 1.520 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8429 reflections
a = 26.6613 (19) Åθ = 3.6–25.9°
b = 7.5766 (5) ŵ = 0.46 mm1
c = 12.6729 (10) ÅT = 173 K
β = 99.729 (6)°Block, 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)
Graphite monochromatorRint = 0.038
ω scansθmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan
[MULABS (Spek, 2009); Blessing, 1995)]
h = 3232
Tmin = 0.841, Tmax = 0.856k = 89
9132 measured reflectionsl = 1515
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)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.051P)2 + 0.8598P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2352 reflectionsΔρmax = 0.29 e Å3
177 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction 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)
Crystal data top
C14H9ClN2OSV = 2523.1 (3) Å3
Mr = 288.74Z = 8
Monoclinic, C2/cMo Kα radiation
a = 26.6613 (19) ŵ = 0.46 mm1
b = 7.5766 (5) ÅT = 173 K
c = 12.6729 (10) Å0.39 × 0.38 × 0.35 mm
β = 99.729 (6)°
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)] = 0.0280 restraints
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.29 e Å3
2352 reflectionsΔρmin = 0.23 e Å3
177 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
Cl10.762196 (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)
H60.33880.03910.32070.033*
C70.34626 (6)0.0292 (2)0.47829 (13)0.0273 (4)
H70.31360.01180.48730.033*
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, º) 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—O12.6 (2)C5—C6—C7—C81.2 (2)
C2—N1—C1—C11174.90 (12)C6—C7—C8—C30.3 (2)
C3—N2—C2—N1177.62 (12)N2—C3—C8—C7178.45 (14)
C3—N2—C2—S11.43 (16)C4—C3—C8—C70.9 (2)
C1—N1—C2—N2171.57 (13)O1—C1—C11—C16165.51 (14)
C1—N1—C2—S19.43 (19)N1—C1—C11—C1611.9 (2)
C4—S1—C2—N21.80 (12)O1—C1—C11—C128.9 (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—C40.12 (18)C1—C11—C12—C13175.22 (13)
N2—C3—C4—C5178.08 (13)C11—C12—C13—C141.1 (2)
C8—C3—C4—C51.4 (2)C11—C12—C13—Cl1178.45 (11)
N2—C3—C4—S11.19 (16)C12—C13—C14—C150.7 (2)
C8—C3—C4—S1179.37 (11)Cl1—C13—C14—C15178.04 (12)
C2—S1—C4—C5177.64 (15)C13—C14—C15—C160.3 (2)
C2—S1—C4—C31.56 (11)C14—C15—C16—C110.8 (2)
C3—C4—C5—C60.5 (2)C12—C11—C16—C150.4 (2)
S1—C4—C5—C6179.62 (12)C1—C11—C16—C15173.83 (14)
C4—C5—C6—C70.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.94 (2)2.02 (2)2.9429 (18)168.9 (17)
Symmetry code: (i) x+1, y, z+3/2.

Experimental details

Crystal data
Chemical formulaC14H9ClN2OS
Mr288.74
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)26.6613 (19), 7.5766 (5), 12.6729 (10)
β (°) 99.729 (6)
V3)2523.1 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.46
Crystal size (mm)0.39 × 0.38 × 0.35
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
[MULABS (Spek, 2009); Blessing, 1995)]
Tmin, Tmax0.841, 0.856
No. of measured, independent and
observed [I > 2σ(I)] reflections
9132, 2352, 2084
Rint0.038
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.079, 1.03
No. of reflections2352
No. of parameters177
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.23

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.94 (2)2.02 (2)2.9429 (18)168.9 (17)
Symmetry code: (i) x+1, y, z+3/2.
 

Acknowledgements

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

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGarden, S. J., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o450–o451.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationWardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o634–o638.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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