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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 May 26;68(Pt 6):o1881–o1882. doi: 10.1107/S1600536812023197

2-Anilino-3-(2-hy­droxy­prop­yl)-4-methyl-1,3-thia­zol-3-ium chloride

Shaaban K Mohamed a, Mehmet Akkurt b,*, Muhammad N Tahir c, Antar A Abdelhamid a, Ali N Khalilov d
PMCID: PMC3379442  PMID: 22719640

Abstract

In the title compound, C13H17N2OS+·Cl, the thia­zolium ring mean plane makes a dihedral angle of 55.46 (9)° with the benzene ring. In the propanol group, the N—C—C—C and N—C—C—O torsion angles are 172.58 (15) and 52.9 (2)°, respectively, and the S—C—C—C torsion angle is 178.99 (18)°. In the crystal, mol­ecules are linked by O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming zigzag chains along [001]. There is also a C—H⋯Cl inter­action present.

Related literature  

The title compound was prepared as part of an ongoing investigation into the synthesis and biological properties of thia­zole compounds: see; Abdel-Wahab et al. (2009); Baia et al. (2008); Lesyk et al. (2007); Mohamed et al. (2012a ,b ); Potikha et al. (2008); Shiradkar et al. (2007); Soliman et al. (2012); Wu & Yang (2007). For related structures, see: Lynch & McClenaghan (2004); Liu et al. (2011); Wang (2011).graphic file with name e-68-o1881-scheme1.jpg

Experimental  

Crystal data  

  • C13H17N2OS+·Cl

  • M r = 284.81

  • Monoclinic, Inline graphic

  • a = 11.7570 (4) Å

  • b = 12.2477 (4) Å

  • c = 10.2954 (3) Å

  • β = 106.532 (1)°

  • V = 1421.21 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 296 K

  • 0.35 × 0.22 × 0.20 mm

Data collection  

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005) T min = 0.898, T max = 0.922

  • 10535 measured reflections

  • 2641 independent reflections

  • 2172 reflections with I > 2σ(I)

  • R int = 0.024

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.032

  • wR(F 2) = 0.084

  • S = 1.03

  • 2641 reflections

  • 166 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.18 e Å−3

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

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023197/su2431sup1.cif

e-68-o1881-sup1.cif (22.9KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023197/su2431Isup2.hkl

e-68-o1881-Isup2.hkl (129.7KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812023197/su2431Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯Cl1 0.82 2.36 3.1681 (16) 169
N1—H1⋯Cl1i 0.86 2.34 3.1675 (14) 163
C11—H11A⋯Cl1i 0.97 2.81 3.6440 (19) 144

Symmetry code: (i) Inline graphic.

Acknowledgments

SKM and AAA thank the Ministry of Higher Education, Egypt, for financial support of this project. Manchester Metropolitan University and the University of Sargodha are also gratefully acknowledged for supporting this study.

supplementary crystallographic information

Comment

Natural compounds such as, bistratamide H, archazolid A & B, siomycin A, didmolamide A, scleritodermin A, etc. (Wu & Yang, 2007) and thiamine (vitamin B1) (Baia et al., 2008), were found to have a thiazol ring system. In addition, thiazole compounds have been reported to exhibit different pharmaceutical properties, for example antibacterial, antifungal (Abdel-Wahab et al., 2009), antitubercular (Shiradkar et al., 2007), anticancer (Lesyk et al., 2007). These compounds have been synthesized using different methods (Potikha et al., 2008). Further to our interest of bioactive compounds (Mohamed et al., 2012a,b; Soliman et al., 2012) we were interested in synthesizing new amino-thiazole derivatives via a one pot reaction protocol. We report herein on the synthesis and crystal structure of the title compound.

In the title compound, (Fig. 1), the dihedral angle between the thiazole ring (S1/N2/C7–C9) and the benzene ring (C1–C6) is 55.46 (9)°. The thiazolium ring is essentialy co-planar with the methyl group which is attached to it, with torsion angle S1—C9—C8—C10 being 178.99 (18)°. In the propanol group, torsion angles N2–C11–C12–C13 and N2–C11–C12–O1 are 172.58 (15) and 52.9 (2)°, respectively. Bond lengths and angles have normal values and are comparable to those reported for similar structures (Lynch & McClenaghan, 2004; Liu et al., 2011; Wang, 2011).

In the crystal, molecules are linked by O-H···Cl, N—H···Cl and C—H···Cl hydrogen bonds, into infinite zigzag chains propagating along the [001] direction (Table 1, Fig. 2).

Experimental

A mixture of 75 mg (1 mmol) 1-aminopropan-2-ol, 135 mg (1 mmol) phenyl isothiocyanate and 93 mg (1 mmol) 1-chloropropan-2-one in 50 ml ethanol was refluxed at 351 K. The reaction was monitored by TLC until completion after four hours then cooled to room temperature. The resulting solid was filtered off, dried under vacuum and recrystallized from ethanol to afford colourless crystals suitable for X-ray analysis [Yield 79%; M.p. 419 K].

Refinement

The H atoms were located in a difference Fourier map. In the final cycles of refinement they were included in calculated poitions and refined using a riding model: N—H = 0.86 Å and C—H = 0.93 Å (aromatic), 0.96 Å (methyl), 0.97 Å (methylene) and 0.98 Å (methine), with Uiso(H) = 1.5Ueq(C) for methyl groups and = 1.2Ueq(C,N) for other H atoms.

Figures

Fig. 1.

Fig. 1.

The molecular structure and atom-numbering scheme for the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Fig. 2.

Fig. 2.

The crystal packing of the title compound, viewing along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Crystal data

C13H17N2OS+·Cl F(000) = 600
Mr = 284.81 Dx = 1.331 Mg m3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 447 reflections
a = 11.7570 (4) Å θ = 3.5–21.2°
b = 12.2477 (4) Å µ = 0.41 mm1
c = 10.2954 (3) Å T = 296 K
β = 106.532 (1)° Rod, colourless
V = 1421.21 (8) Å3 0.35 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer 2641 independent reflections
Radiation source: fine-focus sealed tube 2172 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.024
Detector resolution: 0.81 pixels mm-1 θmax = 25.5°, θmin = 2.5°
ω scans h = −14→11
Absorption correction: multi-scan (SADABS; Bruker, 2005) k = −14→14
Tmin = 0.898, Tmax = 0.922 l = −12→12
10535 measured reflections

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3249P] where P = (Fo2 + 2Fc2)/3
2641 reflections (Δ/σ)max < 0.001
166 parameters Δρmax = 0.17 e Å3
0 restraints Δρmin = −0.18 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)

x y z Uiso*/Ueq
S1 0.53335 (4) 0.36209 (4) −0.02819 (4) 0.0436 (2)
O1 0.92376 (12) 0.25939 (14) 0.20894 (15) 0.0722 (6)
N1 0.58597 (12) 0.35477 (12) 0.24335 (13) 0.0424 (4)
N2 0.73113 (12) 0.41117 (12) 0.13880 (14) 0.0447 (5)
C1 0.47013 (14) 0.31414 (14) 0.23234 (15) 0.0382 (5)
C2 0.40120 (15) 0.36823 (15) 0.30052 (17) 0.0455 (6)
C3 0.29021 (17) 0.3281 (2) 0.29410 (19) 0.0586 (7)
C4 0.24821 (17) 0.2359 (2) 0.22085 (19) 0.0673 (8)
C5 0.31707 (18) 0.18174 (19) 0.15336 (18) 0.0612 (7)
C6 0.42873 (16) 0.22021 (15) 0.15893 (16) 0.0471 (6)
C7 0.62227 (15) 0.37561 (13) 0.13445 (16) 0.0384 (5)
C8 0.74511 (17) 0.42898 (16) 0.00903 (19) 0.0522 (7)
C9 0.64774 (18) 0.40625 (15) −0.08878 (19) 0.0527 (7)
C10 0.8594 (2) 0.4705 (2) −0.0071 (2) 0.0812 (9)
C11 0.82819 (15) 0.41979 (16) 0.26481 (18) 0.0509 (6)
C12 0.88729 (16) 0.31168 (18) 0.31206 (19) 0.0544 (7)
C13 0.99588 (18) 0.3309 (2) 0.4314 (2) 0.0775 (9)
Cl1 0.71127 (4) 0.10568 (4) 0.05541 (4) 0.0553 (2)
H1 0.63390 0.36620 0.32250 0.0510*
H1A 0.86790 0.22510 0.16010 0.1080*
H2 0.42940 0.43100 0.35010 0.0550*
H3 0.24340 0.36390 0.33990 0.0700*
H4 0.17300 0.20970 0.21670 0.0810*
H5 0.28820 0.11910 0.10390 0.0730*
H6 0.47560 0.18360 0.11400 0.0560*
H9 0.64160 0.41330 −0.18050 0.0630*
H10A 0.85460 0.47390 −0.10170 0.1220*
H10B 0.92260 0.42230 0.03820 0.1220*
H10C 0.87460 0.54220 0.03170 0.1220*
H11A 0.79720 0.44960 0.33520 0.0610*
H11B 0.88720 0.47040 0.25100 0.0610*
H12 0.83160 0.26440 0.34050 0.0650*
H13A 1.05130 0.37610 0.40350 0.1160*
H13B 1.03240 0.26220 0.46350 0.1160*
H13C 0.97260 0.36660 0.50290 0.1160*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0486 (3) 0.0486 (3) 0.0332 (2) −0.0003 (2) 0.0112 (2) 0.0015 (2)
O1 0.0544 (8) 0.0909 (12) 0.0737 (10) 0.0018 (8) 0.0221 (8) −0.0187 (8)
N1 0.0389 (7) 0.0577 (9) 0.0305 (7) −0.0068 (7) 0.0095 (6) −0.0046 (6)
N2 0.0429 (8) 0.0501 (9) 0.0424 (8) −0.0073 (7) 0.0145 (6) 0.0013 (6)
C1 0.0368 (9) 0.0496 (10) 0.0277 (8) −0.0008 (8) 0.0083 (7) 0.0037 (7)
C2 0.0466 (10) 0.0562 (11) 0.0339 (9) 0.0062 (8) 0.0120 (8) 0.0041 (8)
C3 0.0417 (10) 0.0936 (16) 0.0433 (11) 0.0091 (11) 0.0167 (9) 0.0074 (10)
C4 0.0415 (11) 0.1137 (19) 0.0455 (11) −0.0179 (12) 0.0106 (9) 0.0083 (12)
C5 0.0641 (13) 0.0781 (15) 0.0387 (10) −0.0288 (11) 0.0103 (9) −0.0025 (9)
C6 0.0539 (11) 0.0570 (11) 0.0318 (9) −0.0069 (9) 0.0146 (8) −0.0020 (8)
C7 0.0415 (9) 0.0381 (9) 0.0364 (9) −0.0001 (7) 0.0123 (7) −0.0007 (7)
C8 0.0578 (11) 0.0555 (12) 0.0491 (11) −0.0065 (9) 0.0245 (10) 0.0092 (9)
C9 0.0665 (12) 0.0551 (12) 0.0417 (10) −0.0017 (9) 0.0239 (10) 0.0093 (8)
C10 0.0748 (15) 0.1027 (19) 0.0776 (15) −0.0227 (14) 0.0402 (13) 0.0156 (14)
C11 0.0423 (10) 0.0619 (12) 0.0494 (11) −0.0140 (9) 0.0144 (8) −0.0084 (9)
C12 0.0401 (10) 0.0747 (14) 0.0485 (11) −0.0024 (9) 0.0127 (8) −0.0044 (9)
C13 0.0479 (12) 0.117 (2) 0.0612 (13) −0.0011 (13) 0.0050 (10) −0.0043 (13)
Cl1 0.0614 (3) 0.0629 (3) 0.0409 (3) 0.0018 (2) 0.0135 (2) 0.0051 (2)

Geometric parameters (Å, º)

S1—C7 1.7111 (17) C11—C12 1.510 (3)
S1—C9 1.723 (2) C12—C13 1.517 (3)
O1—C12 1.407 (2) C2—H2 0.9300
O1—H1A 0.8200 C3—H3 0.9300
N1—C7 1.333 (2) C4—H4 0.9300
N1—C1 1.424 (2) C5—H5 0.9300
N2—C8 1.409 (2) C6—H6 0.9300
N2—C11 1.468 (2) C9—H9 0.9300
N2—C7 1.341 (2) C10—H10A 0.9600
N1—H1 0.8600 C10—H10B 0.9600
C1—C2 1.383 (2) C10—H10C 0.9600
C1—C6 1.387 (2) C11—H11A 0.9700
C2—C3 1.378 (3) C11—H11B 0.9700
C3—C4 1.370 (3) C12—H12 0.9800
C4—C5 1.378 (3) C13—H13A 0.9600
C5—C6 1.381 (3) C13—H13B 0.9600
C8—C9 1.321 (3) C13—H13C 0.9600
C8—C10 1.490 (3)
C7—S1—C9 90.08 (9) C4—C3—H3 120.00
C12—O1—H1A 109.00 C3—C4—H4 120.00
C1—N1—C7 121.86 (14) C5—C4—H4 120.00
C7—N2—C11 123.21 (14) C4—C5—H5 120.00
C8—N2—C11 123.78 (15) C6—C5—H5 120.00
C7—N2—C8 112.74 (14) C1—C6—H6 120.00
C7—N1—H1 119.00 C5—C6—H6 120.00
C1—N1—H1 119.00 S1—C9—H9 124.00
N1—C1—C2 118.53 (15) C8—C9—H9 124.00
N1—C1—C6 120.85 (15) C8—C10—H10A 109.00
C2—C1—C6 120.58 (16) C8—C10—H10B 110.00
C1—C2—C3 119.24 (17) C8—C10—H10C 109.00
C2—C3—C4 120.57 (19) H10A—C10—H10B 109.00
C3—C4—C5 120.2 (2) H10A—C10—H10C 109.00
C4—C5—C6 120.2 (2) H10B—C10—H10C 109.00
C1—C6—C5 119.21 (17) N2—C11—H11A 109.00
S1—C7—N1 123.50 (14) N2—C11—H11B 109.00
S1—C7—N2 112.07 (12) C12—C11—H11A 109.00
N1—C7—N2 124.42 (15) C12—C11—H11B 109.00
N2—C8—C9 112.37 (18) H11A—C11—H11B 108.00
N2—C8—C10 120.73 (16) O1—C12—H12 109.00
C9—C8—C10 126.90 (18) C11—C12—H12 109.00
S1—C9—C8 112.74 (15) C13—C12—H12 109.00
N2—C11—C12 113.11 (15) C12—C13—H13A 109.00
O1—C12—C11 111.54 (16) C12—C13—H13B 109.00
O1—C12—C13 108.34 (16) C12—C13—H13C 109.00
C11—C12—C13 109.20 (18) H13A—C13—H13B 109.00
C1—C2—H2 120.00 H13A—C13—H13C 109.00
C3—C2—H2 120.00 H13B—C13—H13C 109.00
C2—C3—H3 120.00
C9—S1—C7—N1 178.77 (15) C8—N2—C7—N1 −178.65 (16)
C9—S1—C7—N2 −0.17 (14) C8—N2—C11—C12 −94.2 (2)
C7—S1—C9—C8 0.00 (17) N1—C1—C2—C3 −178.13 (16)
C7—N1—C1—C2 −127.80 (17) C2—C1—C6—C5 0.7 (3)
C7—N1—C1—C6 54.5 (2) N1—C1—C6—C5 178.37 (16)
C1—N1—C7—S1 3.0 (2) C6—C1—C2—C3 −0.4 (3)
C1—N1—C7—N2 −178.18 (16) C1—C2—C3—C4 −0.2 (3)
C8—N2—C7—S1 0.27 (19) C2—C3—C4—C5 0.4 (3)
C11—N2—C7—S1 −173.96 (13) C3—C4—C5—C6 −0.1 (3)
C11—N2—C7—N1 7.1 (3) C4—C5—C6—C1 −0.4 (3)
C7—N2—C8—C9 −0.3 (2) N2—C8—C9—S1 0.1 (2)
C11—N2—C8—C9 173.93 (17) C10—C8—C9—S1 −178.99 (18)
C7—N2—C8—C10 178.92 (18) N2—C11—C12—O1 52.9 (2)
C11—N2—C8—C10 −6.9 (3) N2—C11—C12—C13 172.58 (15)
C7—N2—C11—C12 79.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O1—H1A···Cl1 0.82 2.36 3.1681 (16) 169
N1—H1···Cl1i 0.86 2.34 3.1675 (14) 163
C11—H11A···Cl1i 0.97 2.81 3.6440 (19) 144

Symmetry code: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2431).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023197/su2431sup1.cif

e-68-o1881-sup1.cif (22.9KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023197/su2431Isup2.hkl

e-68-o1881-Isup2.hkl (129.7KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536812023197/su2431Isup3.cml

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


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