Startseite Crystal Structure of 4-(2-chloroacetamido)pyridinium chloride monohydrate, C7H10Cl2N2O2
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Crystal Structure of 4-(2-chloroacetamido)pyridinium chloride monohydrate, C7H10Cl2N2O2

  • Mostafa M. Ghorab , Mansour S. Alsaid und Hazem A. Ghabbour EMAIL logo
Veröffentlicht/Copyright: 1. Oktober 2016

Abstract

C7H10Cl2N2O2, monoclinic, P21/c (no. 14), a = 9.8798(3) Å, b = 13.9285(5) Å, c = 7.3161(3) Å, β = 100.512(3)°, V = 989.88(6) Å3, Z = 4, Rgt(F) = 0.0475, wRref(F2) = 0.1178, T = 296 K.

CCDC no.:: 1481643

The crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colourless blocks
Size:0.35 × 0.15 × 0.11 mm
Wavelength: μ:Cu Kα radiation (1.54178 Å) 56.9 cm−1
Diffractometer, scan mode:Bruker SMART, φ and ω
2θmax, completeness:133.2°, >99%
N(hkl)measured, N(hkl)unique, Rint:5770, 1742, 0.060
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ (Iobs), 1328
N(param)refined:134
Programs:SHELX [13], Bruker programs [14]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
Cl10.07709(9)0.47068(7)0.7864(2)0.0791(4)
O10.3756(2)0.47080(16)0.7896(4)0.0544(7)
N10.7764(3)0.6779(2)0.6477(4)0.0382(6)
H1N10.852(4)0.692(3)0.613(5)0.046(10)*
N20.3996(2)0.63334(17)0.7977(4)0.0315(6)
H1N20.350(4)0.687(3)0.808(5)0.048(10)*
C10.6980(3)0.7526(2)0.6801(4)0.0373(7)
H1A0.72990.81620.66870.045*
C20.5733(3)0.7376(2)0.7290(4)0.0343(7)
H2A0.51820.79070.75130.041*
C30.5265(3)0.6444(2)0.7463(4)0.0303(6)
C40.6094(3)0.5682(2)0.7113(4)0.0362(7)
H4A0.58030.50370.72130.043*
C50.7342(3)0.5881(2)0.6620(5)0.0401(8)
H5A0.79140.53660.63770.048*
C60.3299(3)0.5493(2)0.8103(4)0.0330(7)
C70.1890(3)0.5662(2)0.8574(5)0.0429(8)
H7A0.14960.62590.79610.052*
H7B0.19810.57500.99340.052*
O1W1.0095(3)0.7375(2)0.5352(4)0.0540(7)
H2OW1.065(5)0.774(3)0.610(6)0.068(14)*
H1OW1.055(6)0.708(4)0.481(7)0.10(2)*
Cl21.24267(8)0.66507(5)0.33061(11)0.0405(3)

Source of material

A solution of 4-aminopyridine (0.94 g, 0.01 mol) and 2-chloroacetyl chloride (1.12 g, 0.01 mol) in dry dimethylformamide (10 mL) was stirred for 6 h, then the reaction mixture was poured onto ice/water. The obtained solid was crystallized from ethanol to give the title compound. Yield%: 89, m.p. 219.3 °C. IR cm−1 3211 (NH), 3100 (arom.), 2943, 2842 (aliph.), 1609 (CN), 764 (C-Cl). 1H-NMR: 4.3 [s, 2H, CH2], 7.4[s, 1H, NH], 7.9–9.3[m, 4H, Ar—H, AB system], 9.9 [s, 1H, NH]. 13C: 43.6, 109.2, 145.7, 163.5, 169.1. Anal. Calcd for C7H7ClN2O2 (170.60): C, 49.28; H, 4.14; N, 16.42. Found: C, 49.01; H, 4.33; N, 16.12.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The carbon-bound hydrogen atoms were idealized and refind as riding atoms with Uiso set to 1.2Ueq(C).

Discussion

Pyridine derivatives are known for their cytotoxic activity [1]. Combining a pyridinium chloride scaffold with the biologically active 2-chloroacetamide moiety has received great attention as antineoplastic , [2], [3], [4]. Also, acetamide derivatives have been reported as antitumor activity [5]. Based on the aforementioned and as a continuation for our work to synthesize novel anticancer agents , [6], [7], [8], [9], [10], [11], [12], we have designed and synthesized 4-(2-chloroacetamido)pyridinium chloride.

The crystal structure of title compound contains one 4-(2-chloroacetamido)pyridinium cation with one chloride anion and one water molecule in the asymmetric unit. Bond lengths and angles are in the expected ranges. In the crystal structure the molecules are stabilized by intermolecular hydrogen bonds; N1—H1N1⋯O1W, N2—H1N2⋯Cl2i, O1W—H2OW⋯Cl2ii, O1W—H1OW⋯Cl2, and C1—H1A⋯O1iii. The distances of the interactions between them are 1.86(4), 2.34(4), 2.32(5), 2.40(6), and 2.44, respectively. The angles are 173(4), 174(4), 165(4), 160(5), 131, 168.00° and 159°, respectively. Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2.

Acknowledgements:

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for funding of this research through the Research Group Project no. RGP-302.

References

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Received: 2016-5-25
Accepted: 2016-9-2
Published Online: 2016-10-1
Published in Print: 2017-1-1

©2016 Mostafa M. Ghorab et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Editorial
  3. Twenty years of crystal structure publication and the road ahead
  4. Crystal Structures
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  17. Crystal structure of 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea, C17H21ClN2S
  18. Crystal structure of 3-(adamantan-1-yl)-1-(4-bromophenyl)urea, C17H21BrN2O
  19. Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate, C14H14N2O2S
  20. Crystal structure of methyl 2b-ethyl-1a,2a,2b,2b1,3,5,10,11-octahydro-1H-oxireno[2′,3′:6,7]indolizino[8,1-cd]carbazole-4-carboxylate, C21H24N2O3
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  23. Crystal structure of bis(2,6-dihydroxymethyl)pyridine-κ3N,O,O′)-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-bis(6-chloropyridin-2-olato-κO)-bis(nitrato-κ2O,O′)digadolinium(III), C34H30Cl4Gd2N8O14
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  25. Crystal structure of 1-methyl-3-[((naphthalen-2-ylsulfonyl)oxy)imino]indolin-2-one, C19H14N2O4S
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  28. Crystal structure of 2-[(2-oxo-thiazolidine-3-carbonyl)sulfamoyl]-methy-benzoic acid methyl ester, C13H14N2O6S2
  29. Crystal structure of N′-(2-phenylacetyl)thiophene-2-carbohydrazide monohydrate, C13H14N2O3S
  30. Crystal structure of 1,1′-(hexane-1,6-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoro phosphate), C14H24F12N4P2
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  61. Crystal structure of cis-tetrabromidobis(pyridine-κN)platinum(IV), C10H10Br4N2Pt
  62. Crystal structure of (E)-5-((4-chlorophenyl)diazenyl)-2-(5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole, C23H17ClFN5S2
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