(1-Hy-droxy-ethyl-idene)(meth-yl)aza-nium bromide-N-methyl-acetamide (1/1).

The asymmetric unit of the organic hybrid salt, C(3)H(8)NO(+)·Br(-)·C(3)H(7)NO, comprises an N-methyl-acetamide cation, a N-methyl-acetamide mol-ecule and a bromide anion. The amide species are linked head-to-head through a short O⋯H⋯O hydrogen bond, giving a monocation, which is extended by N-H⋯Br hydrogen bonds into chains along the b-axis direction.

Related literature

For general background to frameworks and structural phase transitions, see: Ye et al. (2009 ▶); Zhang et al. (2009 ▶). For the structure of the hemihydro­chloride of N-methyl­acetamide, see: Jaber et al. (1983 ▶).

Experimental

Crystal data

C3H8NO+·Br−·C3H7NO

M = 227.11

Orthorhombic,

a = 6.8830 (14) Å

b = 23.029 (5) Å

c = 13.291 (3) Å

V = 2106.7 (8) Å3

Z = 8

Mo Kα radiation

μ = 3.87 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.461, T max = 0.480

10344 measured reflections

1311 independent reflections

858 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.101

S = 1.06

1311 reflections

80 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016984/zs2188sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016984/zs2188Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016984/zs2188Isup3.cml

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

C3H8NO+·Br−·C3H7NO	F(000) = 928
Mr = 227.11	Dx = 1.432 Mg m−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 3638 reflections
a = 6.8830 (14) Å	θ = 3.0–27.5°
b = 23.029 (5) Å	µ = 3.87 mm−1
c = 13.291 (3) Å	T = 298 K
V = 2106.7 (8) Å3	Block, colorless
Z = 8	0.20 × 0.20 × 0.20 mm

Rigaku SCXmini diffractometer	858 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −29→29
Tmin = 0.461, Tmax = 0.480	l = −17→17
10344 measured reflections	2 standard reflections every 150 reflections
1311 independent reflections	intensity decay: none

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.3335P] where P = (Fo2 + 2Fc2)/3
1311 reflections	(Δ/σ)max < 0.001
80 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.5000	0.147343 (18)	0.08336 (4)	0.0651 (3)
H1	0.5000	0.233 (2)	0.196 (4)	0.069 (16)*
N1	0.5000	0.25929 (16)	0.2388 (3)	0.0553 (10)
O1	0.5000	0.35425 (13)	0.2661 (3)	0.0714 (10)
C2	0.5000	0.4921 (2)	0.2594 (4)	0.0578 (12)
H2	0.5000	0.573 (2)	0.277 (4)	0.092 (19)*
N2	0.5000	0.54618 (17)	0.2301 (3)	0.0635 (11)
O2	0.5000	0.45173 (14)	0.1949 (3)	0.0717 (10)
C5	0.5000	0.31197 (19)	0.2038 (3)	0.0506 (11)
C6	0.5000	0.24321 (19)	0.3449 (3)	0.0658 (14)
H7A	0.5414	0.2758	0.3846	0.099*	0.50
H7B	0.5874	0.2113	0.3552	0.099*	0.50
H7C	0.3712	0.2320	0.3647	0.099*	0.50
C4	0.5000	0.3231 (2)	0.0925 (3)	0.0695 (15)
H8A	0.5940	0.3526	0.0769	0.104*	0.50
H8B	0.3734	0.3359	0.0719	0.104*	0.50
H8C	0.5326	0.2880	0.0575	0.104*	0.50
C3	0.5000	0.4790 (2)	0.3693 (4)	0.0724 (15)
H9A	0.4649	0.5133	0.4061	0.109*	0.50
H9B	0.6273	0.4666	0.3894	0.109*	0.50
H9C	0.4078	0.4488	0.3831	0.109*	0.50
C1	0.5000	0.5647 (2)	0.1246 (4)	0.0804 (16)
H10A	0.6291	0.5759	0.1053	0.121*	0.50
H10B	0.4138	0.5972	0.1165	0.121*	0.50
H10C	0.4571	0.5332	0.0828	0.121*	0.50
H3	0.5000	0.401 (3)	0.231 (5)	0.15 (3)*

	U11	U22	U33	U12	U13	U23
Br1	0.0934 (5)	0.0415 (3)	0.0606 (4)	0.000	0.000	−0.0013 (2)
N1	0.074 (3)	0.039 (2)	0.052 (2)	0.000	0.000	−0.001 (2)
O1	0.124 (3)	0.0397 (18)	0.051 (2)	0.000	0.000	−0.0049 (15)
C2	0.060 (3)	0.046 (3)	0.068 (3)	0.000	0.000	−0.005 (3)
N2	0.077 (3)	0.042 (2)	0.071 (3)	0.000	0.000	−0.007 (2)
O2	0.115 (3)	0.0394 (17)	0.061 (2)	0.000	0.000	−0.0052 (16)
C5	0.054 (3)	0.045 (3)	0.052 (3)	0.000	0.000	−0.002 (2)
C6	0.084 (4)	0.054 (3)	0.059 (3)	0.000	0.000	0.008 (2)
C4	0.099 (4)	0.057 (3)	0.052 (3)	0.000	0.000	0.003 (2)
C3	0.104 (4)	0.055 (3)	0.058 (3)	0.000	0.000	−0.003 (3)
C1	0.100 (4)	0.062 (3)	0.080 (4)	0.000	0.000	0.022 (3)

N1—C5	1.299 (5)	C6—H7B	0.9600
N1—C6	1.458 (6)	C6—H7C	0.9600
N1—H1	0.83 (4)	C4—H8A	0.9600
O1—C5	1.278 (5)	C4—H8B	0.9600
O1—H3	1.16 (7)	C4—H8C	0.9600
C2—O2	1.266 (5)	C3—H9A	0.9600
C2—N2	1.304 (5)	C3—H9B	0.9600
C2—C3	1.491 (6)	C3—H9C	0.9600
N2—C1	1.466 (6)	C1—H10A	0.9600
N2—H2	0.89 (5)	C1—H10B	0.9600
C5—C4	1.502 (6)	C1—H10C	0.9600
C6—H7A	0.9600
C5—N1—C6	125.7 (4)	H7B—C6—H7C	109.5
C5—N1—H1	116 (4)	C5—C4—H8A	109.5
C6—N1—H1	118 (4)	C5—C4—H8B	109.5
C5—O1—H3	116 (3)	H8A—C4—H8B	109.5
O2—C2—N2	119.9 (5)	C5—C4—H8C	109.5
O2—C2—C3	121.0 (4)	H8A—C4—H8C	109.5
N2—C2—C3	119.0 (4)	H8B—C4—H8C	109.5
C2—N2—C1	124.3 (5)	C2—C3—H9A	109.5
C2—N2—H2	118 (4)	C2—C3—H9B	109.5
C1—N2—H2	118 (4)	H9A—C3—H9B	109.5
C2—O2—H3	115 (3)	C2—C3—H9C	109.5
O1—C5—N1	118.6 (4)	H9A—C3—H9C	109.5
O1—C5—C4	120.6 (4)	H9B—C3—H9C	109.5
N1—C5—C4	120.8 (4)	N2—C1—H10A	109.5
N1—C6—H7A	109.5	N2—C1—H10B	109.5
N1—C6—H7B	109.5	H10A—C1—H10B	109.5
H7A—C6—H7B	109.5	N2—C1—H10C	109.5
N1—C6—H7C	109.5	H10A—C1—H10C	109.5
H7A—C6—H7C	109.5	H10B—C1—H10C	109.5
C6—N1—C5—O1	0.00	C1—N2—C2—O2	0.00
C6—N1—C5—C4	180.00	C1—N2—C2—C3	180.00

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br1i	0.89 (5)	2.51 (5)	3.402 (5)	178 (5)
O1—H3···O2	1.16 (7)	1.27 (7)	2.437 (4)	179 (6)
N1—H1···Br1	0.83 (4)	2.48 (5)	3.304 (4)	174 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Br1i	0.89 (5)	2.51 (5)	3.402 (5)	178 (5)
O1—H3⋯O2	1.16 (7)	1.27 (7)	2.437 (4)	179 (6)
N1—H1⋯Br1	0.83 (4)	2.48 (5)	3.304 (4)	174 (5)

Symmetry code: (i) .