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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1059.
Published online 2008 May 10. doi:  10.1107/S160053680801355X
PMCID: PMC2961632

N-Hydroxy-N-methyl­ammonium chloride

Abstract

In the crystal structure of the title compound, CH6NO+·Cl, the cations and anions are linked by N–H(...)Cl and O–H(...)Cl hydrogen bonds into an undulating layer motif [Schläfli symbol: 4(8).6(8).8(2)]. All non-H atoms lie on a mirror plane.

Related literature

Only the cell dimensions of N-methyhydroxy­lammonium chloride have hitherto been reported; see: Toft & Jerslev (1967 [triangle]).

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Object name is e-64-o1059-scheme1.jpg

Experimental

Crystal data

  • CH6NO+·Cl
  • M r = 83.52
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1059-efi1.jpg
  • a = 7.8084 (3) Å
  • b = 8.7109 (3) Å
  • c = 6.0232 (1) Å
  • V = 409.69 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.73 mm−1
  • T = 100 (2) K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.839, T max = 0.899
  • 3330 measured reflections
  • 558 independent reflections
  • 493 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.070
  • S = 1.07
  • 558 reflections
  • 40 parameters
  • 6 restraints
  • All H-atom parameters refined
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.26 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: X-SEED (Barbour, 2001 [triangle]); OLEX (Dolomanov et al., 2003 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801355X/tk2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801355X/tk2270Isup2.hkl

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

Acknowledgments

I thank the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

We are interested in the crystal structures of small organic molecules, molecules whose asymmetric unit consist of four or five non-hydrogen atoms only. N-Methylhydroxylammonium chloride (Scheme I) provides an example of such a system. However, the crystal structure is not known with only unit-cell dimensions reported (Toft & Jerslev, 1967).

The structure (Fig. 1) consists of cations and anions that are linked by N–H···Cl and O–H···Cl hydrogen bonds into an undulating layer motif [Schläfli symbol: 4(8).6(8).8(2)], Fig. 2 & Table 1. The non-hydrogen atoms lie on a mirror plane.

Experimental

The chemical as purchased from the Aldrich Chemical Company was crystalline.

Refinement

All hydrogen atoms were located in a difference Fouier map, and were refined with distance restraints (C–H 0.99±0.01, N–H 0.88±0.01 and O–H 0.84±0.01 Å). For the methyl group, an additional H···H = 1.59±0.01 Å was imposed. The temperature factors were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of N-methylhydroxylammonium chloride at the 70% probability level.
Fig. 2.
OLEX (Dolomanov et al., 2003) representation of the hydrogen-bonded layer structure.

Crystal data

CH6NO+·ClF000 = 176
Mr = 83.52Dx = 1.354 Mg m3
Orthorhombic, PbcmMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2c 2bCell parameters from 1402 reflections
a = 7.8084 (3) Åθ = 2.6–28.2º
b = 8.7109 (3) ŵ = 0.73 mm1
c = 6.0232 (1) ÅT = 100 (2) K
V = 409.69 (2) Å3Prism, colorless
Z = 40.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer558 independent reflections
Radiation source: fine-focus sealed tube493 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
T = 100(2) Kθmax = 28.4º
ω scansθmin = 2.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −10→8
Tmin = 0.839, Tmax = 0.899k = −11→11
3330 measured reflectionsl = −8→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024All H-atom parameters refined
wR(F2) = 0.070  w = 1/[σ2(Fo2) + (0.0402P)2 + 0.0529P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
558 reflectionsΔρmax = 0.28 e Å3
40 parametersΔρmin = −0.26 e Å3
6 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.15 (1)

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

xyzUiso*/Ueq
Cl0.35777 (6)0.42790 (6)0.25000.0433 (2)
O0.1297 (2)0.1511 (2)0.25000.0389 (3)
N0.2586 (2)0.0376 (2)0.25000.0300 (3)
C0.1739 (3)−0.1127 (3)0.25000.0457 (5)
H10.184 (3)0.2349 (17)0.25000.048 (6)*
H20.3265 (17)0.0482 (17)0.366 (2)0.041 (4)*
H30.2644 (18)−0.190 (2)0.25000.048 (6)*
H40.1075 (14)−0.121 (2)0.1170 (8)0.064 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl0.0455 (3)0.0591 (4)0.0254 (3)−0.0196 (2)0.0000.000
O0.0315 (7)0.0324 (7)0.0529 (8)0.0032 (5)0.0000.000
N0.0282 (6)0.0336 (7)0.0282 (7)0.0016 (5)0.0000.000
C0.053 (1)0.033 (1)0.051 (1)−0.004 (1)0.0000.000

Geometric parameters (Å, °)

O—N1.411 (2)N—H20.88 (1)
N—C1.467 (3)C—H30.98 (1)
O—H10.84 (1)C—H40.96 (1)
N—O—H1104.5 (16)N—C—H3107.0 (12)
O—N—C107.70 (14)N—C—H4108.0 (11)
O—N—H2110.8 (10)H3—C—H4110.0 (9)
C—N—H2111.3 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O—H1···Cl0.84 (1)2.16 (1)2.998 (1)171 (2)
N—H2···Cli0.88 (1)2.33 (1)3.1241 (4)149 (1)

Symmetry codes: (i) x, −y+1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2270).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dolomanov, O. V., Blake, A. J., Champness, N. R. & Schröder, M. (2003). J. Appl. Cryst.36, 1283–1284.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Toft, L. & Jerslev, B. R. (1967). Acta Chem. Scand.21, 1383–1384.
  • Westrip, S. P. (2008). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography