N-Hydroxy-N-methyl­ammonium chloride

Ng, S.W.

doi:10.1107/S160053680801355X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1059

doi:10.1107/S160053680801355X

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N-Hydroxy-N-methylammonium chloride

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 6 May 2008; accepted 7 May 2008; online 10 May 2008)

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 ).

Experimental

Crystal data

CH₆NO⁺·Cl⁻
M_r = 83.52
Orthorhombic, P b c m
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 ) 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[F² > 2σ(F²)] = 0.024
wR(F²) = 0.070
S = 1.07
558 reflections
40 parameters
6 restraints
All H-atom parameters refined
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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 code: (i) $[x, -y+{\script{1\over 2}}, -z+1]$ .

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: X-SEED (Barbour, 2001 ); OLEX (Dolomanov et al., 2003 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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

Computing details top

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).

Figures top

	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.

N-Hydroxy-N-methylammonium chloride top

Crystal data top

CH₆NO⁺·Cl⁻	F(000) = 176
M_r = 83.52	D_x = 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 = 2.6–28.2°
b = 8.7109 (3) Å	µ = 0.73 mm⁻¹
c = 6.0232 (1) Å	T = 100 K
V = 409.69 (2) Å³	Prism, colorless
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	558 independent reflections
Radiation source: fine-focus sealed tube	493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 28.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
T_min = 0.839, T_max = 0.899	k = −11→11
3330 measured reflections	l = −8→8

Refinement top

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(F_o²) + (0.0402P)² + 0.0529P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
558 reflections	Δρ_max = 0.28 e Å⁻³
40 parameters	Δρ_min = −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)

Crystal data top

CH₆NO⁺·Cl⁻	V = 409.69 (2) Å³
M_r = 83.52	Z = 4
Orthorhombic, Pbcm	Mo Kα radiation
a = 7.8084 (3) Å	µ = 0.73 mm⁻¹
b = 8.7109 (3) Å	T = 100 K
c = 6.0232 (1) Å	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	558 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	493 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.899	R_int = 0.029
3330 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	6 restraints
wR(F²) = 0.070	All H-atom parameters refined
S = 1.07	Δρ_max = 0.28 e Å⁻³
558 reflections	Δρ_min = −0.26 e Å⁻³
40 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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 code: (i) x, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	CH₆NO⁺·Cl⁻
M_r	83.52
Crystal system, space group	Orthorhombic, Pbcm
Temperature (K)	100
a, b, c (Å)	7.8084 (3), 8.7109 (3), 6.0232 (1)
V (Å³)	409.69 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.839, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	3330, 558, 493
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.070, 1.07
No. of reflections	558
No. of parameters	40
No. of restraints	6
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001); OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

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 code: (i) x, −y+1/2, −z+1.

Acknowledgements

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

References

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