Acta Cryst. (2008). E64, o1059 [ doi:10.1107/S160053680801355X ]
In the crystal structure of the title compound, CH6NO+·Cl-, the cations and anions are linked by N-H
Cl and O-HCl hydrogen bonds into an undulating layer motif [Schläfli symbol: 4(8).6(8).8(2)]. All non-H atoms lie on a mirror plane.
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.
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2008).
![[Figure 1]](./tk2270fig1thm.gif)
| Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of N-methylhydroxylammonium chloride at the 70% probability level. |
![[Figure 2]](./tk2270fig2thm.gif)
| Fig. 2. OLEX (Dolomanov et al., 2003) representation of the hydrogen-bonded layer structure. |
| CH6NO+·Cl– | F000 = 176 |
| Mr = 83.52 | Dx = 1.354 Mg m−3 |
| Orthorhombic, Pbcm | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2c 2b | Cell parameters from 1402 reflections |
| a = 7.8084 (3) Å | θ = 2.6–28.2º |
| b = 8.7109 (3) Å | µ = 0.73 mm−1 |
| c = 6.0232 (1) Å | T = 100 (2) K |
| V = 409.69 (2) Å3 | Prism, colorless |
| Z = 4 | 0.25 × 0.20 × 0.15 mm |
| Bruker SMART APEX diffractometer | 558 independent reflections |
| Radiation source: fine-focus sealed tube | 493 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.029 |
| T = 100(2) K | θmax = 28.4º |
| ω scans | θmin = 2.6º |
| Absorption correction: Multi-scan (SADABS; Sheldrick, 1996) | h = −10→8 |
| Tmin = 0.839, Tmax = 0.899 | k = −11→11 |
| 3330 measured reflections | l = −8→8 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.024 | All 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 reflections | Δρmax = 0.28 e Å−3 |
| 40 parameters | Δρmin = −0.26 e Å−3 |
| 6 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.15 (1) |
| CH6NO+·Cl– | V = 409.69 (2) Å3 |
| Mr = 83.52 | Z = 4 |
| Orthorhombic, Pbcm | Mo Kα |
| a = 7.8084 (3) Å | µ = 0.73 mm−1 |
| b = 8.7109 (3) Å | T = 100 (2) K |
| c = 6.0232 (1) Å | 0.25 × 0.20 × 0.15 mm |
| Bruker SMART APEX diffractometer | 558 independent reflections |
| Absorption correction: Multi-scan (SADABS; Sheldrick, 1996) | 493 reflections with I > 2σ(I) |
| Tmin = 0.839, Tmax = 0.899 | Rint = 0.029 |
| 3330 measured reflections |
| R[F2 > 2σ(F2)] = 0.024 | 6 restraints |
| wR(F2) = 0.070 | All H-atom parameters refined |
| S = 1.07 | Δρmax = 0.28 e Å−3 |
| 558 reflections | Δρmin = −0.26 e Å−3 |
| 40 parameters |
| x | y | z | Uiso*/Ueq | ||
| Cl | 0.35777 (6) | 0.42790 (6) | 0.2500 | 0.0433 (2) | |
| O | 0.1297 (2) | 0.1511 (2) | 0.2500 | 0.0389 (3) | |
| N | 0.2586 (2) | 0.0376 (2) | 0.2500 | 0.0300 (3) | |
| C | 0.1739 (3) | −0.1127 (3) | 0.2500 | 0.0457 (5) | |
| H1 | 0.184 (3) | 0.2349 (17) | 0.2500 | 0.048 (6)* | |
| H2 | 0.3265 (17) | 0.0482 (17) | 0.366 (2) | 0.041 (4)* | |
| H3 | 0.2644 (18) | −0.190 (2) | 0.2500 | 0.048 (6)* | |
| H4 | 0.1075 (14) | −0.121 (2) | 0.1170 (8) | 0.064 (5)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl | 0.0455 (3) | 0.0591 (4) | 0.0254 (3) | −0.0196 (2) | 0.000 | 0.000 |
| O | 0.0315 (7) | 0.0324 (7) | 0.0529 (8) | 0.0032 (5) | 0.000 | 0.000 |
| N | 0.0282 (6) | 0.0336 (7) | 0.0282 (7) | 0.0016 (5) | 0.000 | 0.000 |
| C | 0.053 (1) | 0.033 (1) | 0.051 (1) | −0.004 (1) | 0.000 | 0.000 |
| O—N | 1.411 (2) | N—H2 | 0.88 (1) |
| N—C | 1.467 (3) | C—H3 | 0.98 (1) |
| O—H1 | 0.84 (1) | C—H4 | 0.96 (1) |
| N—O—H1 | 104.5 (16) | N—C—H3 | 107.0 (12) |
| O—N—C | 107.70 (14) | N—C—H4 | 108.0 (11) |
| O—N—H2 | 110.8 (10) | H3—C—H4 | 110.0 (9) |
| C—N—H2 | 111.3 (10) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O—H1···Cl | 0.84 (1) | 2.16 (1) | 2.998 (1) | 171 (2) |
| N—H2···Cli | 0.88 (1) | 2.33 (1) | 3.1241 (4) | 149 (1) |
| Symmetry codes: (i) x, −y+1/2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O—H1···Cl | 0.84 (1) | 2.16 (1) | 2.998 (1) | 171 (2) |
| N—H2···Cli | 0.88 (1) | 2.33 (1) | 3.1241 (4) | 149 (1) |
| Symmetry codes: (i) x, −y+1/2, −z+1. |
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.
Toft, L. & Jerslev, B. R. (1967). Acta Chem. Scand. 21, 1383–1384.
Westrip, S. P. (2008). publCIF. In preparation.
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.