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 ▶).

Experimental

Crystal data

• CH₆NO⁺·Cl⁻

• M _r = 83.52

• Orthorhombic,

• a = 7.8084 (3) Å

• b = 8.7109 (3) Å

• c = 6.0232 (1) Å

• V = 409.69 (2) ų

• 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[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

• Δρ_max = 0.28 e Å⁻³

• Δρ_min = −0.26 e Å⁻³

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 ▶).

Supplementary Material

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

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) .

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+·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

Data collection

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

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)

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

	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)*

Atomic displacement parameters (Ų)

	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—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, °)

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.