Hydrogen-bond inter-actions in morpholinium bromide.

In the title compound, C(4)H(10)NO(+)·Br(-), which was synthesized by dehydration of diethano-lamine with HBr, morpholinium and bromide ions are linked into chains by N-H⋯Br hydrogen bonds describing a C(2) (1)(4) graph-set motif. Weaker bifurcated N-H⋯Br inter-actions join centrosymmetrically related chains through alternating binary graph-set R(4) (2)(8) and R(2) (2)(4) motifs, to form ladders along [100]. In addition, C-H⋯O inter-actions between centrosymmetric morpholinium cations link ladders, via[Formula: see text](8) motifs, to yield sheets parallel to (101), which in turn are crosslinked by weak C-H⋯O inter-actions, related across a glide plane, to form a three-dimensional network.

Related literature

For the structures of related morpholinium salts, see: Loehlin & Okasako (2007 ▶); Mafud et al. (2011 ▶); Swaminathan et al. (1976 ▶); Koroniak et al. (2000 ▶); Turnbull (1997 ▶); Mazur et al. (2007 ▶); Yao (2010 ▶); Christensen et al. (1993 ▶). For the synthesis, see: Pettit et al. (1964 ▶). For the graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C4H10NO+·Br−

M = 168.04

Monoclinic,

a = 6.1247 (2) Å

b = 10.3063 (3) Å

c = 10.1141 (3) Å

β = 100.312 (2)°

V = 628.12 (3) Å3

Z = 4

Mo Kα radiation

μ = 6.44 mm−1

T = 173 K

0.40 × 0.20 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: integration (face indexed absorption corrections carried out with XPREP; Sheldrick, 2008 ▶) T min = 0.183, T max = 0.595

11662 measured reflections

1516 independent reflections

1314 reflections with I > 2σ(I)

R int = 0.210

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.03

1516 reflections

64 parameters

H-atom parameters constrained

Δρmax = 1.07 e Å−3

Δρmin = −1.38 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and WinGX (Farrugia, 1997 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035598/lr2027sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035598/lr2027Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035598/lr2027Isup3.cml

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

C4H10NO+·Br−	F(000) = 336
Mr = 168.04	Dx = 1.777 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5677 reflections
a = 6.1247 (2) Å	θ = 2.9–28.3°
b = 10.3063 (3) Å	µ = 6.44 mm−1
c = 10.1141 (3) Å	T = 173 K
β = 100.312 (2)°	Needle, colourless
V = 628.12 (3) Å3	0.40 × 0.20 × 0.09 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1516 independent reflections
Radiation source: fine-focus sealed tube	1314 reflections with I > 2σ(I)
graphite	Rint = 0.210
φ and ω scans	θmax = 28.0°, θmin = 2.9°
Absorption correction: integration (face indexed absorption corrections carried out with XPREP; Sheldrick, 2008)	h = −8→8
Tmin = 0.183, Tmax = 0.595	k = −13→13
11662 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0518P)2] where P = (Fo2 + 2Fc2)/3
1516 reflections	(Δ/σ)max = 0.002
64 parameters	Δρmax = 1.07 e Å−3
0 restraints	Δρmin = −1.38 e Å−3

Experimental. Intensity data were collected on a Bruker APEX II CCD area detector diffractometer with graphite monochromated Mo Kα radiation (50 kV, 30 mA) using the APEX 2 (Bruker, 2005) data collection software. The collection method involved ω-scans of width 0.5° and 512 x 512 bit data frames. Data reduction was carried out using the program SAINT-Plus (Bruker, 2005). The crystal structure was solved by direct methods using SHELXTL (Sheldrick, 2008). Non-hydrogen atoms were first refined isotropically followed by anisotropic refinement by full matrix least-squares calculations based on F2 using SHELXTL.

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 > 2sigma(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
Br1	0.74904 (4)	0.11971 (3)	0.07284 (3)	0.02454 (16)
O1	0.2489 (4)	0.10940 (17)	0.4694 (3)	0.0263 (5)
N1	0.2813 (4)	0.0830 (2)	0.1937 (2)	0.0199 (5)
H1A	0.3739	0.0758	0.1318	0.024*
H1B	0.1372	0.0808	0.1480	0.024*
C1	0.3228 (5)	0.2082 (3)	0.2657 (3)	0.0243 (6)
H1C	0.2788	0.2807	0.2024	0.029*
H1D	0.4831	0.2170	0.3026	0.029*
C4	0.3199 (5)	−0.0280 (3)	0.2893 (3)	0.0246 (6)
H4A	0.4801	−0.0347	0.3272	0.029*
H4B	0.2732	−0.1098	0.2410	0.029*
C2	0.1926 (5)	0.2149 (3)	0.3781 (3)	0.0273 (6)
H2A	0.2241	0.2980	0.4268	0.033*
H2B	0.0319	0.2119	0.3404	0.033*
C3	0.1915 (5)	−0.0094 (3)	0.4004 (3)	0.0272 (6)
H3A	0.0308	−0.0095	0.3628	0.033*
H3B	0.2221	−0.0824	0.4646	0.033*

	U11	U22	U33	U12	U13	U23
Br1	0.0153 (2)	0.0332 (2)	0.0242 (2)	−0.00109 (9)	0.00118 (14)	−0.00764 (10)
O1	0.0358 (13)	0.0301 (11)	0.0127 (10)	0.0010 (8)	0.0031 (9)	0.0004 (7)
N1	0.0159 (11)	0.0289 (11)	0.0147 (11)	0.0018 (8)	0.0021 (9)	−0.0013 (8)
C1	0.0259 (14)	0.0220 (13)	0.0238 (14)	−0.0055 (10)	0.0014 (11)	0.0010 (10)
C4	0.0274 (14)	0.0238 (14)	0.0213 (14)	0.0042 (10)	0.0014 (11)	−0.0004 (10)
C2	0.0336 (16)	0.0246 (14)	0.0225 (15)	0.0050 (11)	0.0018 (13)	−0.0047 (11)
C3	0.0340 (15)	0.0245 (14)	0.0230 (14)	−0.0033 (11)	0.0053 (12)	0.0037 (11)

O1—C3	1.422 (3)	C1—H1D	0.9900
O1—C2	1.428 (3)	C4—C3	1.495 (4)
N1—C1	1.481 (3)	C4—H4A	0.9900
N1—C4	1.490 (3)	C4—H4B	0.9900
N1—H1A	0.9200	C2—H2A	0.9900
N1—H1B	0.9200	C2—H2B	0.9900
C1—C2	1.502 (4)	C3—H3A	0.9900
C1—H1C	0.9900	C3—H3B	0.9900
C3—O1—C2	109.1 (2)	N1—C4—H4B	109.6
C1—N1—C4	110.9 (2)	C3—C4—H4B	109.6
C1—N1—H1A	109.5	H4A—C4—H4B	108.1
C4—N1—H1A	109.5	O1—C2—C1	110.8 (2)
C1—N1—H1B	109.5	O1—C2—H2A	109.5
C4—N1—H1B	109.5	C1—C2—H2A	109.5
H1A—N1—H1B	108.1	O1—C2—H2B	109.5
N1—C1—C2	110.1 (2)	C1—C2—H2B	109.5
N1—C1—H1C	109.6	H2A—C2—H2B	108.1
C2—C1—H1C	109.6	O1—C3—C4	111.3 (2)
N1—C1—H1D	109.6	O1—C3—H3A	109.4
C2—C1—H1D	109.6	C4—C3—H3A	109.4
H1C—C1—H1D	108.1	O1—C3—H3B	109.4
N1—C4—C3	110.2 (2)	C4—C3—H3B	109.4
N1—C4—H4A	109.6	H3A—C3—H3B	108.0
C3—C4—H4A	109.6
C4—N1—C1—C2	−52.4 (3)	N1—C1—C2—O1	57.9 (3)
C1—N1—C4—C3	52.1 (3)	C2—O1—C3—C4	62.3 (3)
C3—O1—C2—C1	−62.4 (3)	N1—C4—C3—O1	−57.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.92	2.52	3.331 (2)	148
N1—H1A···Br1i	0.92	2.89	3.389 (2)	115
N1—H1B···Br1ii	0.92	2.40	3.292 (2)	164
C4—H4A···O1iii	0.99	2.52	3.366 (4)	143
C1—H1C···O1iv	0.99	2.59	3.498 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1	0.92	2.52	3.331 (2)	148
N1—H1A⋯Br1i	0.92	2.89	3.389 (2)	115
N1—H1B⋯Br1ii	0.92	2.40	3.292 (2)	164
C4—H4A⋯O1iii	0.99	2.52	3.366 (4)	143
C1—H1C⋯O1iv	0.99	2.59	3.498 (4)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .