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Crystal structure of benzylthiouronium chloride, C8H11ClN2S

  • Marius Maritz , Eric C. Hosten ORCID logo and Richard Betz ORCID logo EMAIL logo
Published/Copyright: October 5, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 1

Abstract

C8H11ClN2S, orthorhombic, Pbca (no. 61), a = 11.3126(6) Å, b = 8.3567(4) Å, c = 20.4130(11) Å, V = 1929.76(17) Å3, Z = 8, Rgt(F) = 0.0240, wRref(F2) = 0.0680, T = 200 K.

CCDC no.: 2033285

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.51 × 0.45 × 0.29 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.56 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:28.3°, >99 %
N(hkl)measured, N(hkl)unique, Rint:16553, 2398, 0.022
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2077
N(param)refined:125
Programs:Bruker [1], [2], SHELX [3], WinGX/ORTEP [4], Mercury [5], PLATON [6]
Table 2:

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

AtomxyzUiso*/Ueq
S10.55112 (3)0.39898 (4)0.404030 (15)0.02740 (9)
N10.41950 (10)0.66140 (14)0.42571 (6)0.0283 (2)
H7110.4078 (14)0.753 (2)0.4414 (8)0.036 (4)*
H7120.3581 (14)0.606 (2)0.4219 (8)0.036 (4)*
N20.61698 (10)0.67443 (14)0.45016 (6)0.0310 (2)
H7210.6812 (16)0.627 (2)0.4586 (9)0.047 (5)*
H7220.6070 (14)0.766 (2)0.4670 (8)0.043 (5)*
C10.52448 (11)0.59542 (14)0.42863 (6)0.0235 (2)
C20.41370 (11)0.33877 (14)0.36493 (6)0.0274 (2)
H2A0.41260.22060.36130.033*
H2B0.34700.37060.39350.033*
C30.39410 (10)0.40884 (14)0.29786 (6)0.0241 (2)
C40.47472 (11)0.38159 (14)0.24754 (6)0.0281 (3)
H40.54460.32190.25590.034*
C50.45361 (12)0.44104 (16)0.18535 (6)0.0331 (3)
H50.50890.42160.15120.040*
C60.35232 (13)0.52865 (17)0.17262 (7)0.0372 (3)
H60.33800.56870.12980.045*
C70.27218 (12)0.55783 (19)0.22206 (7)0.0397 (3)
H70.20290.61860.21340.048*
C80.29289 (11)0.49806 (16)0.28464 (7)0.0326 (3)
H80.23750.51830.31860.039*
Cl10.66773 (3)0.50164 (3)0.027813 (16)0.02983 (9)

Source of material

The compound was obtained commerciually (Hopkin & Williams Ltd.). Crystals suitable for the diffraction study were taken directly from the provided product.

Experimental details

Carbon-bound H atoms were placed in calculated positions (C–H 0.95 Å for aromatic carbon atoms, C–H 0.99 Å for methylene groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

All nitrogen-bound H atoms were located on a difference Fourier map and refined freely.

Comment

The effect of size and steric presence of large ions on chemical and spectroscopic properties of compounds have been a focus of research for many decades. Among the many effects that can be attributed to the spatial requirements of counterions have been the glass transition temperature in ionomers [7], surfactant modifying properties [8], the charge transfer in radical ions [9] and polymer-modified electrodes [10] as well as the structural and vibrational spectroscopic behaviour of DNA building blocks [11]. The benefit of chosing the adequate size of counterions to crystallize ionic compounds has been confirmed and reviewed several times [12]. Thiouronium derivatives are especially interesting in this context as they constitute a compound class that has been known for many decades. Their ease of synthesis in connection with their ready crystallizability – especially as picrates – has played a major role in the identification of alkyl halides [13]. However, due to the size of the picrate anion the metrical parameters of the pertaining thiouronium cations might not be free from crystal-packing-induced distortions. To eliminate this potential biased view, the crystal structure of the title compound was determined to account for this factor by opting for chloride as a much smaller anion.

The structure solution shows the presence of the benzylthiouronium cation with chloride as the counterion. The two sulphur-carbon bond lengths differ markedly from one another with values of 1.7430(12) Å and 1.8186(13) Å with the shorter bond formed towards the thiourea motif. The formal C=S double bond is longer than the most-commonly reported values for the pertaining bond in other thiouronium derivatives whose metrical parameters have been deposited with the Cambridge Structural Database [14]. The least squares planes as defined by the non-hydrogen atoms of the aromatic moiety and the thiourea moiety enclose an angle of 82.04(4)°.

In the crystal structure, all nitrogen-bonded hydrogen atoms act as donors in classical N–H⃛Cl hydrogen bonds. Furthermore, one of the hydrogen atoms of the methylene group gives rise to C–H⃛Cl contacts whose range falls by more than 0.1 Å below the sum of van-der–Waals radii of the atoms participating in them. In terms of graph-set analysis, [15], [16], the descriptor for these contacts is DDDDD at the unary level. In total, these interactions connect the entities present in the crystal structure to double layers perpendicular to the crystallographic c axis. π Stacking is not a prominent stabilizing feature of the structure as the shortest intercentroid distance was measured at 5.0240(8) Å.

Corresponding author: Richard Betz, Department of Chemistry, Nelson Mandela University, Summerstrand Campus (South), UniversityWay, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa, E-mail:

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: R. Betz thanks the NRF for financial support.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-08-30
Accepted: 2020-09-22
Published Online: 2020-10-05
Published in Print: 2021-01-26

© 2020 Marius Maritz et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 3-oxo-urs-12-en-28-oic acid, C30H46O3·1/6H2O
  4. The crystal structure of (3S,12R,20R,24R)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25–triol–ethyl acetate (4/1), C34H56O6⋅ 0.25(C4H8O2)
  5. A new polymorph of tetrakis(dimethylammonium) catena-poly[tetrakis(μ2-sulfato-κ2O:O′)dizinc(II)], Zn2C8H32N4O16S4
  6. Crystal structure of 10-oxysophoridine, C15H22N2O2
  7. The crystal structure of (5R,8R,9R,10R,12R,13R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O4
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  9. The crystal structure of hexakis(2-(pyridin-2-ylamino)pyridin-1-ium) decavanadate(V) dihydrate, C60H64N18O30V10
  10. Preparation and crystal structure of a cationic olefin polymerization precatalyst: (1,7-bis(2,6–dichlorophenyl)-1,7-di-aza-4-oxo-heptan-1,4,7-triyl)dimethyl zirconium(IV), C18H20Cl4N2OZr
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  12. Synthesis and crystal structure of hexaaquacopper(II) 2,5-dicarboxyterephthalate, C10H16O14Cu
  13. The crystal structure of (8R,10R,12R,14R)- 12-hydroxy-16-(5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)- 4,4,8,10,14-pentamethyltetradecahydro-3H- cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O5
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  17. Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO
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  19. Crystal structure of N,N-diphenylformamide, C13H11NO
  20. Crystal structure of (E)-2-(3,5-bis(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen- 1(2H)-one, C20H14F6O2
  21. Crystal structure of ortho-methoxy benzaldehyde, C8H8O2 – a second polymorph and deposition of 3D coordinates
  22. Crystal structure of catena-poly[diaqua-bis(μ2-2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O:O')-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O,O')yttrium(III)], C51H79O11Y
  23. Crystal structure of benzylthiouronium chloride, C8H11ClN2S
  24. Synthesis and crystal structure of tert-butyl (2′R,3R,3′R,4a′R,9a′S)-1-acetyl-5-chloro-3″-methyl-2,5″,9′-trioxo-1″-phenyl-1″,4a′,5″,9a′-tetrahydro-1′H,3′H,9′H-dispiro[indoline-3,4′-xanthene-2′,4″-pyrazole]-3′-carboxylate, C36H32ClN3O7
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  28. Synthesis and crystal structure of bis{2-bromo-6-((E)-((4-((E)-1-(methoxy-imino)ethyl)phenyl)imino)methyl)phenolato- κ2N,O}zinc(II)-methanol(1/2), C65H60Br4N8O9Zn2
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https://doi.org/10.1515/ncrs-2020-0429
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 3-oxo-urs-12-en-28-oic acid, C30H46O3·1/6H2O
  4. The crystal structure of (3S,12R,20R,24R)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25–triol–ethyl acetate (4/1), C34H56O6⋅ 0.25(C4H8O2)
  5. A new polymorph of tetrakis(dimethylammonium) catena-poly[tetrakis(μ2-sulfato-κ2O:O′)dizinc(II)], Zn2C8H32N4O16S4
  6. Crystal structure of 10-oxysophoridine, C15H22N2O2
  7. The crystal structure of (5R,8R,9R,10R,12R,13R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O4
  8. Synthesis, crystal structure and optical property of 1,6-bis(p-tolylthio)pyrene, C30H22S2
  9. The crystal structure of hexakis(2-(pyridin-2-ylamino)pyridin-1-ium) decavanadate(V) dihydrate, C60H64N18O30V10
  10. Preparation and crystal structure of a cationic olefin polymerization precatalyst: (1,7-bis(2,6–dichlorophenyl)-1,7-di-aza-4-oxo-heptan-1,4,7-triyl)dimethyl zirconium(IV), C18H20Cl4N2OZr
  11. The crystal structure of fac-tricarbonyl(4,4-dimethyl-2,2-dipyridyl-κ2N,N′)- (pyrazole-κN)rhenium(I) nitrate, C18H16O3N4Re
  12. Synthesis and crystal structure of hexaaquacopper(II) 2,5-dicarboxyterephthalate, C10H16O14Cu
  13. The crystal structure of (8R,10R,12R,14R)- 12-hydroxy-16-(5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)- 4,4,8,10,14-pentamethyltetradecahydro-3H- cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O5
  14. Structure of the mixed crystal (S)-(6-(bromo/chloro)-2-methoxy-2,6-dihydroquinolin-3-yl)(phenyl)methanol, C17H14Br0.5Cl0.5NO2
  15. The crystal structure of trans-tetraaqua-bis(4-acetylphenoxyacetato-κ1O)manganese(II), C20H26O12Mn
  16. Crystal structure of (E)-2-(4-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  17. Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO
  18. The crystal structure of dipentaerthritol hexanitrate, C10H16N6O19
  19. Crystal structure of N,N-diphenylformamide, C13H11NO
  20. Crystal structure of (E)-2-(3,5-bis(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen- 1(2H)-one, C20H14F6O2
  21. Crystal structure of ortho-methoxy benzaldehyde, C8H8O2 – a second polymorph and deposition of 3D coordinates
  22. Crystal structure of catena-poly[diaqua-bis(μ2-2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O:O')-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O,O')yttrium(III)], C51H79O11Y
  23. Crystal structure of benzylthiouronium chloride, C8H11ClN2S
  24. Synthesis and crystal structure of tert-butyl (2′R,3R,3′R,4a′R,9a′S)-1-acetyl-5-chloro-3″-methyl-2,5″,9′-trioxo-1″-phenyl-1″,4a′,5″,9a′-tetrahydro-1′H,3′H,9′H-dispiro[indoline-3,4′-xanthene-2′,4″-pyrazole]-3′-carboxylate, C36H32ClN3O7
  25. Crystal structure of 2-hydroxy-4-methoxy benzaldehyde, C8H8O3
  26. Crystal structure of poly[diaqua-(m3-3′,5′-dicarboxy-[1,1′-biphenyl]-3,4-dicarboxylato-K4O,O′:O″:O‴) cadmium(II)], C16H11O10Cd
  27. Crystal structure of {tetraaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)}-{triaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)} – water – acetone (1/1/8/2)
  28. Synthesis and crystal structure of bis{2-bromo-6-((E)-((4-((E)-1-(methoxy-imino)ethyl)phenyl)imino)methyl)phenolato- κ2N,O}zinc(II)-methanol(1/2), C65H60Br4N8O9Zn2
  29. Crystal structure of benzenesulphonic acid
  30. Crystal structure of N-benzyl-N-nicotinoyl-nicotine amide C19H15N3O2
  31. Crystal structure of poly[aqua(μ3-2,4-diamino-benzenesulfonato-κ4N:N′,O:O′)silver(I)], C12H18O8N4S2Ag2
  32. Crystal structure of 1,4-bis(methylpyridinium benzene) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C26H18N6NiS4
  33. Crystal structure of the Cu(II) complex chlorido-(6-oxo-2-phenyl-1,6-dihydropyrimidine-4-carboxylato-k2N,O)-(phenanthroline-k2N,N')copper(II), C23H15ClCuN4O3
  34. Crystal structure of phenarsazine chloride acetic acid solvate, C14H13AsClNO2
  35. Crystal structure of poly[aqua-(μ2-3,3′,4,5′-biphenyl tetracarboxylate- κ3O,O′:O′′) -(μ2-4,4′-bis(pyrid-4-yl)biphenyl-κ2N:N′)zinc(II)], C27H18NO9Zn
  36. Crystal structure of catena-poly[(μ2-3-amino-benzenedisulfonato-κ2N:O)-bis (3-methyl-isoquinoline-κN)silver(I)], C26H24N3O3SAg
  37. Crystal structure of 2-((4-Aminophenyl)thio)acetic acid, C8H9NO2S
  38. Crystal structure of phenarsazine chloride dimethylsulfoxide solvate, C14H15AsClNOS
  39. Synthesis and crystal structure of 2-azido-N-phenylacetamide, C8H8N4O
  40. Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6
  41. Crystal structure of benzanthrone – a redetermination for correct molecular geometry and localization of hydrogen atoms
  42. Crystal structure of 4-bromobenzaldehyde – complete redetermination at 200 K, C7H5BrO
  43. Crystal structure and spectroscopic properties of chlorido{hydridotris[3-,5-dimethylpyrazol-1-yl-κN3]borato}(3-,5-dimethylpyrazol-1-yl-κN)copper(II), C20H30BClCuN8
  44. The crystal structure of 4-((2-hydroxynaphthalen-1-yl)(pyrrolidin-1-yl)methyl)benzonitrile, C22H20N2O
  45. Crystal structure of 4-ethyl-3-phenylisoquinolin-1(2H)-one, C17H15NO
  46. Crystal structure of (tricyclohexylphosphane-κP)-[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-k1S]gold(I), C26H40AuFNOPS
  47. Crystal structure of (3S,8R,10R,12R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H54O4
  48. The crystal structure of 2-[(S)-1-(naphthalen-1-yl)ethyl]-2,3,7,7a- tetrahydro-3a,6-epoxyisoindol-1(6H)-one, C19H20NO2
  49. Crystal structure of {hydridotris[3-(t-butyl)-5-isopropylpyrazol-1-yl-κN3]borato}thallium(I), C30H52BN6Tl
  50. Synthesis and crystal structure of 1-octyl-3-phenylquinoxalin-2(1H)-one, C22H26N2O
  51. The crystal structure of 2,6-difluorophenol, C6H4F2O
  52. 4-(9H-Fluoren-9-yl)-4-methylmorpholin-4-ium bromide, C18H20BrNO
  53. The crystal structure of 2,4-dimethylimidazole monohydrate, C5H10N2O
  54. The crystal structure of 1,2-dimethylimidazole, C5H8N2
  55. The crystal structure of 3-ammonio-4-aminobenzoate, C7H8N2O2 – a second polymorph
  56. The crystal structure of 4-hydroxy-2,5-bis(1-methyl-1H-imidazol-3-ium-2-ylthio)-3,6-dioxocyclohexa-1,4-dienolate chloride monohydrate, C14H15N4O5S2Cl
  57. The crystal structure of butyrylferrocene, C14H16FeO
  58. The crystal structure of bi-1,1′-cyclopentane-1,1′-diol, C10H18O2
  59. The crystal structure of 2-iso-propylimidazole, C6H10N2
  60. The crystal structure of aqua-tris (1,3-diphenylpropane-1,3-dionato-κ2O,O′)-lanthanum(III), C45H35LaO7
  61. Crystal structure of (3E,5E)-3,5-bis-4-methoxy-3-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  62. The crystal structure of 3,5-dichloro-6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one, C6Cl2N4O5
  63. Crystal structure of carbonyl(2-methylquinolin-8-olato-κ2N,O)(triphenylarsine-κAs)rhodium(I), C29H23AsNO2Rh
  64. Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
  65. Crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-k2O,O′)(triphenylarsine-κAs)rhodium(I), C24H19AsNO3Rh
  66. Crystal structure of catena-poly[triqua-bis(μ2-4-carboxy-2-(1H-tetrazol-1-yl)-1H-imidazole-5-carboxylato-k3N,O:O′)barium(II)] tetrahydrate, C14H14BaN12O15
  67. Crystal structure of (E)-3′,6′-bis(ethylamino)-2-((quinoxalin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C35H32N6O2
  68. Crystal structure of diaqua-bis(μ2-5-chloro-salicylato-κ3O,O′:O′)-bis(5-chloro-salicylato-κ2O,O′)-bis(1,10-phenanthroline-κ2N,N′) dilead(II) – water (1/2), C52H36C14N4O14Pb2·2(H2O)
  69. Crystal structure of (E)-2-(4-ethoxycarbonyl-3,5-dimethyl-2-(pyrrole-2-ylmethyleneamino)-3′,6′-dihydroxylspiro[isoindoline-1,9′-xanthen]-3-one-methanol (1/1), C31H29N3O7
  70. The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2
  71. Crystal structure of (E)-2-(4-fluoro-2-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  72. The crystal structure of N-(2-methoxy-4,5-bis[phenylselanyl]phenyl)picolinamide, C25H20N2O2Se2
  73. The crystal structure of (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1- carboxamide monohydrate, C14H14BrN3O3
  74. Crystal structure of fac-tricarbonyl-(nitrato-k1O)-bis(pyridine-κN)-rhenium, C13H10O6N3Re
  75. Crystal structure of (E)-2-(((1H-pyrrol-2-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one — methanol (1/2), C27H25N3O6
  76. The crystal structure of 4-amino-N′-(4-aminobenzoyl)benzohydrazide monohydrate, C14H16N4O3
  77. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 5-hydroxyisophthalate monohydrate, C12H20N8O6S2
  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
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