4-Methyl-morpholinium bromide.

The six-membered ring in the title salt, C(5)H(12)NO(+)·Br(-), has a chair conformation. In the crystal, the cations are linked to the anions by N-H⋯Br hydrogen bonds.

Related literature

For background to phase transition materials, see: Hang et al. (2009 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C5H12NO+·Br−

M = 182.07

Monoclinic,

a = 7.3282 (15) Å

b = 7.4170 (15) Å

c = 7.3928 (15) Å

β = 92.72 (3)°

V = 401.37 (14) Å3

Z = 2

Mo Kα radiation

μ = 5.04 mm−1

T = 293 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.178, T max = 0.365

4192 measured reflections

995 independent reflections

866 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 0.97

995 reflections

50 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.72 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017447/ng2770sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017447/ng2770Isup2.hkl

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

C5H12NO+·Br−	F(000) = 184
Mr = 182.07	Dx = 1.506 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 0 reflections
a = 7.3282 (15) Å	θ = 3.8–27.5°
b = 7.4170 (15) Å	µ = 5.04 mm−1
c = 7.3928 (15) Å	T = 293 K
β = 92.72 (3)°	Prism, colourless
V = 401.37 (14) Å3	0.40 × 0.30 × 0.20 mm
Z = 2

Rigaku Mercury2 diffractometer	995 independent reflections
Radiation source: fine-focus sealed tube	866 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.8°
CCD_Profile_fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.178, Tmax = 0.365	l = −9→9
4192 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.1157P] where P = (Fo2 + 2Fc2)/3
995 reflections	(Δ/σ)max < 0.001
50 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.5268 (5)	0.7500	0.3399 (6)	0.0810 (14)
N1	0.1476 (4)	0.7500	0.2465 (5)	0.0352 (7)
H1B	0.1507	0.7500	0.1250	0.062 (16)*
C1	0.4418 (5)	0.5939 (7)	0.2671 (6)	0.0749 (13)
H1A	0.4478	0.5968	0.1377	0.096 (16)*
H1C	0.5054	0.4884	0.3106	0.110 (18)*
C2	0.2434 (4)	0.5854 (5)	0.3149 (5)	0.0488 (8)
H2A	0.1864	0.4810	0.2604	0.054 (10)*
H2B	0.2359	0.5765	0.4438	0.059 (11)*
C5	−0.0464 (6)	0.7500	0.2948 (7)	0.0484 (11)
H5A	−0.1058	0.6449	0.2455	0.061 (11)*
H5B	−0.0534	0.7500	0.4234	0.059 (16)*
Br1	0.15472 (6)	0.7500	−0.18624 (5)	0.0464 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0332 (17)	0.143 (4)	0.066 (3)	0.000	−0.0037 (18)	0.000
N1	0.0288 (16)	0.047 (2)	0.0300 (17)	0.000	0.0003 (13)	0.000
C1	0.047 (2)	0.116 (4)	0.062 (3)	0.034 (2)	0.0023 (18)	−0.007 (3)
C2	0.0464 (17)	0.0512 (19)	0.0482 (19)	0.0130 (15)	−0.0023 (13)	−0.0017 (15)
C5	0.032 (2)	0.056 (3)	0.057 (3)	0.000	0.004 (2)	0.000
Br1	0.0608 (3)	0.0470 (3)	0.0314 (3)	0.000	0.0005 (2)	0.000

O1—C1	1.409 (5)	C1—H1A	0.9600
O1—C1i	1.409 (5)	C1—H1C	0.9578
N1—C5	1.482 (5)	C2—H2A	0.9597
N1—C2i	1.485 (4)	C2—H2B	0.9596
N1—C2	1.485 (4)	C5—H5A	0.9562
N1—H1B	0.8997	C5—H5B	0.9550
C1—C2	1.514 (5)
C1—O1—C1i	110.5 (4)	C2—C1—H1C	110.2
C5—N1—C2i	111.2 (2)	H1A—C1—H1C	108.0
C5—N1—C2	111.2 (2)	N1—C2—C1	109.3 (3)
C2i—N1—C2	110.6 (3)	N1—C2—H2A	109.3
C5—N1—H1B	108.1	C1—C2—H2A	109.9
C2i—N1—H1B	107.8	N1—C2—H2B	110.3
C2—N1—H1B	107.8	C1—C2—H2B	109.6
O1—C1—C2	110.9 (3)	H2A—C2—H2B	108.4
O1—C1—H1A	108.8	N1—C5—H5A	109.4
C2—C1—H1A	108.9	N1—C5—H5B	109.7
O1—C1—H1C	110.1	H5A—C5—H5B	109.5
C1i—O1—C1—C2	−61.8 (5)	C2i—N1—C2—C1	−54.4 (4)
C5—N1—C2—C1	−178.4 (3)	O1—C1—C2—N1	57.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Br1	0.90	2.30	3.202 (4)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Br1	0.90	2.30	3.202 (4)	179