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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1805.
Published online 2009 July 11. doi:  10.1107/S1600536809025616
PMCID: PMC2977499

S-1,3-Benzothia­zol-2-yl (2Z)-2-(2-amino-1,3-thia­zol-4-yl)-2-(methoxy­imino)­ethane­thio­ate

Abstract

The title compound, C13H10N4O2S3, is an acyl­ating agent which belongs to the thia­zole class of organic compounds. The dihedral angle between the benzene and thiazole rings, which are fused to each other, is 1.2 (2)° so the overall benzothiazole system is almost planar. Inter­molecular N—H(...)N inter­actions and weak C—H(...)O inter­actions between symmetry-related mol­ecules stabilize the crystal structure, forming three different ring motifs [R 2 2(8), R 2 2(10) and R 2 2(16)] in three dimensions.

Related literature

For background literature, see: Khanna et al. (1999 [triangle]). For related structures, see: Radha (1985 [triangle]); Laurent & Durant (1981 [triangle]). For graph set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1805-scheme1.jpg

Experimental

Crystal data

  • C13H10N4O2S3
  • M r = 350.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1805-efi1.jpg
  • a = 13.9725 (9) Å
  • b = 5.0156 (3) Å
  • c = 21.7664 (14) Å
  • β = 90.001 (3)°
  • V = 1525.40 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.50 mm−1
  • T = 296 K
  • 0.31 × 0.11 × 0.07 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.941, T max = 0.972
  • 16828 measured reflections
  • 3829 independent reflections
  • 2096 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.145
  • S = 1.03
  • 3829 reflections
  • 200 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025616/pv2172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025616/pv2172Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant to the Materials Chemistry Laboratory at GC University, Lahore, Pakistan. The title compound was kindly provided by Pharmagen Ltd, Lahore, Pakistan.

supplementary crystallographic information

Comment

The title compound, (I), is a standard acylating agent for the synthesis of different cephalosporins derivatives (Khanna et al., 1999).

The title compound (Fig. 1) is composed of two components, a benzothiazole and an acyl group having 2-amino thiazole moiety. The N3 atoms of 2-aminothiazole moieties of molecules of (I) lying about inversion centers form intermolecular hydrogen bonds of the type N–H···N with N1 and N4 atoms resulting in dimers and form 8 and 10-membered rings which could be expressed in graph set notation as R22(8) and R22(10) motifs (Bernstein et al., 1995). In addition, there is a rather weak C–H···O type interaction, resulting in an R22(16) motif about inversion centers. The hydrogen bonding geometry is presented in Table 1 and Fig. 2. The crystal structures of compounds related to (I) have been reported (Radha, 1985; Laurent & Durant, 1981) .

Experimental

The compound was dissolved in methanol and ethyl acetate mixture (20:80 v/v %). The light yellow prismatic crystals were obtained after two days.

Refinement

The H-atoms were refined geometrically and treated as riding atoms with C—H distances, 0.93 and 0.96 Å for aryl and methyl groups, respectively, and N–H = 0.86 Å with Uiso(H) = 1.2 times aromatic C and N atoms and Uiso(H) = 1.5 times methyl C atoms.

Figures

Fig. 1.
The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
Fig. 2.
Unit cell packing for (I) showing hydrogen bonds drawn as dashed lines.

Crystal data

C13H10N4O2S3F(000) = 720
Mr = 350.43Dx = 1.526 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2744 reflections
a = 13.9725 (9) Åθ = 2.4–22.8°
b = 5.0156 (3) ŵ = 0.50 mm1
c = 21.7664 (14) ÅT = 296 K
β = 90.001 (3)°Prism, light yellow
V = 1525.40 (17) Å30.31 × 0.11 × 0.07 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer3829 independent reflections
Radiation source: fine-focus sealed tube2096 reflections with I > 2σ(I)
graphiteRint = 0.054
[var phi] and ω scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −18→18
Tmin = 0.941, Tmax = 0.972k = −6→6
16828 measured reflectionsl = −29→28

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0695P)2] where P = (Fo2 + 2Fc2)/3
3829 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.34 e Å3

Special details

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)

xyzUiso*/Ueq
S11.09909 (5)0.53325 (15)0.33403 (3)0.0473 (2)
S20.82219 (5)1.20705 (16)0.47275 (4)0.0481 (2)
S30.62042 (6)1.30442 (19)0.51641 (4)0.0658 (3)
O10.73807 (14)0.7981 (4)0.41758 (10)0.0515 (6)
O20.76884 (15)1.2729 (4)0.32595 (10)0.0599 (6)
N10.97196 (15)0.6544 (4)0.41510 (10)0.0342 (5)
N20.85575 (16)1.1371 (5)0.31772 (11)0.0457 (6)
N31.07870 (17)0.3179 (5)0.44609 (11)0.0508 (7)
H3A1.05150.30010.48130.061*
H3B1.12730.22090.43680.061*
N40.73303 (16)0.9626 (5)0.56704 (11)0.0468 (6)
C11.04521 (18)0.4975 (5)0.40561 (12)0.0352 (6)
C21.0159 (2)0.7693 (5)0.31617 (13)0.0428 (7)
H11.01290.85980.27890.051*
C30.95521 (18)0.8065 (5)0.36329 (12)0.0340 (6)
C40.87134 (19)0.9811 (5)0.36324 (12)0.0370 (6)
C50.80041 (19)0.9594 (5)0.41574 (13)0.0379 (7)
C60.72758 (19)1.1345 (6)0.52336 (14)0.0427 (7)
C70.5768 (2)1.1236 (6)0.57791 (14)0.0516 (8)
C80.6472 (2)0.9518 (6)0.59907 (14)0.0451 (7)
C90.6272 (2)0.7821 (7)0.64769 (16)0.0641 (10)
H100.67330.66390.66220.077*
C100.5376 (3)0.7925 (8)0.67398 (17)0.0729 (11)
H90.52320.67980.70660.088*
C110.4697 (3)0.9652 (8)0.65302 (19)0.0755 (11)
H80.40990.96760.67190.091*
C120.4867 (2)1.1338 (8)0.60535 (19)0.0762 (11)
H70.44001.25160.59160.091*
C130.7520 (3)1.4460 (6)0.27606 (16)0.0641 (10)
H11A0.80781.55370.26910.096*
H11B0.69851.55900.28520.096*
H11C0.73841.34310.23990.096*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0469 (4)0.0640 (5)0.0309 (4)0.0148 (4)0.0129 (3)0.0034 (4)
S20.0494 (5)0.0563 (5)0.0387 (5)−0.0072 (4)0.0129 (4)−0.0009 (4)
S30.0557 (5)0.0812 (6)0.0605 (6)0.0223 (4)0.0143 (4)0.0168 (5)
O10.0441 (12)0.0557 (12)0.0547 (15)−0.0042 (10)0.0139 (10)−0.0033 (10)
O20.0565 (13)0.0793 (15)0.0439 (14)0.0303 (11)0.0118 (11)0.0226 (11)
N10.0349 (12)0.0442 (13)0.0236 (13)0.0022 (10)0.0041 (10)0.0040 (10)
N20.0469 (14)0.0550 (14)0.0353 (15)0.0137 (12)0.0067 (11)0.0056 (12)
N30.0567 (16)0.0613 (15)0.0342 (15)0.0246 (13)0.0114 (12)0.0107 (13)
N40.0419 (14)0.0621 (15)0.0363 (15)0.0042 (12)0.0108 (11)0.0046 (13)
C10.0354 (14)0.0429 (15)0.0274 (15)−0.0001 (12)0.0043 (12)−0.0033 (13)
C20.0465 (16)0.0536 (17)0.0283 (16)0.0077 (13)0.0091 (13)0.0076 (13)
C30.0369 (14)0.0399 (14)0.0251 (15)−0.0006 (12)0.0031 (12)0.0006 (12)
C40.0399 (15)0.0444 (16)0.0266 (16)0.0013 (12)0.0046 (12)0.0021 (13)
C50.0359 (14)0.0439 (16)0.0339 (17)0.0095 (13)0.0040 (12)0.0060 (13)
C60.0391 (15)0.0539 (17)0.0351 (17)0.0019 (13)0.0079 (13)−0.0053 (14)
C70.0427 (16)0.069 (2)0.043 (2)−0.0017 (15)0.0105 (14)−0.0055 (16)
C80.0426 (16)0.0606 (19)0.0320 (17)−0.0018 (14)0.0081 (13)−0.0045 (15)
C90.060 (2)0.084 (2)0.049 (2)−0.0032 (18)0.0113 (17)0.0124 (19)
C100.077 (3)0.095 (3)0.046 (2)−0.021 (2)0.020 (2)0.006 (2)
C110.052 (2)0.109 (3)0.066 (3)−0.010 (2)0.0231 (19)−0.011 (2)
C120.047 (2)0.109 (3)0.072 (3)0.013 (2)0.0178 (19)0.001 (2)
C130.075 (2)0.066 (2)0.052 (2)0.0228 (18)−0.0030 (18)0.0160 (18)

Geometric parameters (Å, °)

S1—C21.704 (3)C2—C31.344 (4)
S1—C11.740 (3)C2—H10.9300
S2—C61.759 (3)C3—C41.463 (4)
S2—C51.782 (3)C4—C51.517 (3)
S3—C71.728 (3)C7—C81.387 (4)
S3—C61.729 (3)C7—C121.394 (4)
O1—C51.190 (3)C8—C91.387 (4)
O2—N21.404 (3)C9—C101.378 (5)
O2—C131.410 (4)C9—H100.9300
N1—C11.308 (3)C10—C111.364 (5)
N1—C31.382 (3)C10—H90.9300
N2—C41.281 (3)C11—C121.360 (5)
N3—C11.344 (3)C11—H80.9300
N3—H3A0.8600C12—H70.9300
N3—H3B0.8600C13—H11A0.9600
N4—C61.286 (4)C13—H11B0.9600
N4—C81.388 (3)C13—H11C0.9600
C2—S1—C188.90 (13)N4—C6—S2123.9 (2)
C6—S2—C599.42 (13)S3—C6—S2119.61 (18)
C7—S3—C688.79 (15)C8—C7—C12121.4 (3)
N2—O2—C13110.1 (2)C8—C7—S3109.5 (2)
C1—N1—C3109.6 (2)C12—C7—S3129.1 (3)
C4—N2—O2110.2 (2)C9—C8—C7119.5 (3)
C1—N3—H3A120.0C9—C8—N4125.6 (3)
C1—N3—H3B120.0C7—C8—N4115.0 (3)
H3A—N3—H3B120.0C10—C9—C8118.5 (3)
C6—N4—C8110.3 (2)C10—C9—H10120.8
N1—C1—N3124.9 (2)C8—C9—H10120.8
N1—C1—S1114.7 (2)C11—C10—C9121.2 (4)
N3—C1—S1120.37 (19)C11—C10—H9119.4
C3—C2—S1110.7 (2)C9—C10—H9119.4
C3—C2—H1124.7C12—C11—C10121.9 (3)
S1—C2—H1124.7C12—C11—H8119.1
C2—C3—N1116.1 (2)C10—C11—H8119.1
C2—C3—C4126.0 (2)C11—C12—C7117.5 (4)
N1—C3—C4117.8 (2)C11—C12—H7121.2
N2—C4—C3120.2 (2)C7—C12—H7121.2
N2—C4—C5121.0 (2)O2—C13—H11A109.5
C3—C4—C5118.7 (2)O2—C13—H11B109.5
O1—C5—C4123.6 (3)H11A—C13—H11B109.5
O1—C5—S2125.2 (2)O2—C13—H11C109.5
C4—C5—S2111.29 (19)H11A—C13—H11C109.5
N4—C6—S3116.5 (2)H11B—C13—H11C109.5
C13—O2—N2—C4179.6 (3)C8—N4—C6—S30.8 (3)
C3—N1—C1—N3−177.9 (3)C8—N4—C6—S2179.6 (2)
C3—N1—C1—S11.6 (3)C7—S3—C6—N4−0.9 (3)
C2—S1—C1—N1−1.1 (2)C7—S3—C6—S2−179.7 (2)
C2—S1—C1—N3178.4 (2)C5—S2—C6—N487.6 (3)
C1—S1—C2—C30.3 (2)C5—S2—C6—S3−93.60 (19)
S1—C2—C3—N10.6 (3)C6—S3—C7—C80.7 (2)
S1—C2—C3—C4−176.0 (2)C6—S3—C7—C12−179.4 (4)
C1—N1—C3—C2−1.4 (3)C12—C7—C8—C91.4 (5)
C1—N1—C3—C4175.5 (2)S3—C7—C8—C9−178.6 (3)
O2—N2—C4—C3176.5 (2)C12—C7—C8—N4179.6 (3)
O2—N2—C4—C50.7 (4)S3—C7—C8—N4−0.4 (3)
C2—C3—C4—N2−7.4 (4)C6—N4—C8—C9177.9 (3)
N1—C3—C4—N2176.1 (2)C6—N4—C8—C7−0.3 (4)
C2—C3—C4—C5168.5 (3)C7—C8—C9—C10−0.8 (5)
N1—C3—C4—C5−8.1 (4)N4—C8—C9—C10−178.8 (3)
N2—C4—C5—O192.6 (3)C8—C9—C10—C110.0 (6)
C3—C4—C5—O1−83.3 (3)C9—C10—C11—C120.2 (6)
N2—C4—C5—S2−86.7 (3)C10—C11—C12—C70.4 (6)
C3—C4—C5—S297.4 (2)C8—C7—C12—C11−1.2 (6)
C6—S2—C5—O1−1.4 (3)S3—C7—C12—C11178.8 (3)
C6—S2—C5—C4177.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···N1i0.862.293.106 (3)158
N3—H3B···N4i0.862.162.997 (3)165
C12—H7···O1ii0.932.513.198 (3)131

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2172).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2007). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Khanna, J. M., Handa, V. K., Dandala, R. & Aryan, R. C. (1999). US Patent No. 5 869 649.
  • Laurent, G. & Durant, F. (1981). Cryst. Struct. Commun 10, 1007–1014.
  • Radha, A. (1985). Z. Kristallogr.171, 225–228.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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