2-(Morpholinium-4-yl)ethyl-ammonium sulfate methanol monosolvate.

In the title compound, C(6)H(16)N(2)O(2+)·SO(4) (2-)·CH(3)OH, the morpholinium ring of the dication adopts a chair conformation. The crystal structure is stabilized by an extensive three-dimensional network of inter-molecular O-H⋯O, N-H⋯O, O-H⋯S and N-H⋯S hydrogen bonds.

Related literature

For supra­molecular compounds derived from the self-assembly of inorganic acids with organic amines, see: Xu (2010 ▶); Akhtar et al. (2010 ▶); Zhang & Liu (2010 ▶); Hemamalini & Fun (2010 ▶); SiMa (2010 ▶).

Experimental

Crystal data

C6H16N2O2+·SO4 2−·CH4O

M = 260.31

Monoclinic,

a = 15.593 (14) Å

b = 8.573 (8) Å

c = 9.483 (9) Å

β = 106.395 (11)°

V = 1216.0 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.946, T max = 0.951

5674 measured reflections

2462 independent reflections

1726 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.286

S = 1.08

2462 reflections

151 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.87 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010846/sj2757sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010846/sj2757Isup2.hkl

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

C6H16N2O2+·SO42−·CH4O	F(000) = 560
Mr = 260.31	Dx = 1.422 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2104 reflections
a = 15.593 (14) Å	θ = 2.2–27.7°
b = 8.573 (8) Å	µ = 0.28 mm−1
c = 9.483 (9) Å	T = 298 K
β = 106.395 (11)°	Block, colorless
V = 1216.0 (19) Å3	0.20 × 0.18 × 0.18 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2462 independent reflections
Radiation source: fine-focus sealed tube	1726 reflections with I > 2σ(I)
graphite	Rint = 0.049
ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→14
Tmin = 0.946, Tmax = 0.951	k = −10→10
5674 measured reflections	l = −10→12

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.286	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.1965P)2] where P = (Fo2 + 2Fc2)/3
2462 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.62 e Å−3
1 restraint	Δρmin = −0.87 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
S1	0.35803 (6)	0.59946 (11)	0.06772 (9)	0.0369 (4)
O1	0.3987 (2)	0.5157 (3)	0.2047 (3)	0.0523 (8)
O2	0.3969 (2)	0.7579 (3)	0.0786 (3)	0.0557 (8)
O3	0.3768 (2)	0.5166 (4)	−0.0531 (3)	0.0574 (9)
O4	0.2617 (2)	0.6167 (5)	0.0429 (5)	0.0772 (11)
O5	0.1552 (3)	0.3688 (5)	1.0088 (7)	0.1071 (18)
H5	0.1834	0.4507	1.0182	0.161*
O6	0.9107 (2)	0.4451 (4)	0.5902 (3)	0.0606 (9)
N1	0.7246 (2)	0.5104 (4)	0.4511 (3)	0.0371 (7)
N2	0.51382 (19)	0.7510 (4)	0.3894 (3)	0.0403 (8)
H2A	0.5402	0.8420	0.3841	0.061*
H2B	0.4754	0.7621	0.4426	0.061*
H2C	0.4846	0.7192	0.2993	0.061*
C1	0.7681 (3)	0.5356 (5)	0.6131 (4)	0.0469 (10)
H1A	0.7247	0.5183	0.6673	0.056*
H1B	0.7893	0.6422	0.6300	0.056*
C2	0.8462 (3)	0.4232 (7)	0.6667 (5)	0.0593 (12)
H2D	0.8736	0.4392	0.7709	0.071*
H2E	0.8242	0.3168	0.6528	0.071*
C3	0.8723 (3)	0.4061 (6)	0.4418 (5)	0.0558 (12)
H3A	0.8513	0.2991	0.4351	0.067*
H3B	0.9174	0.4135	0.3895	0.067*
C4	0.7949 (3)	0.5129 (5)	0.3698 (4)	0.0471 (10)
H4A	0.8168	0.6186	0.3682	0.056*
H4B	0.7684	0.4801	0.2690	0.056*
C5	0.6558 (2)	0.6314 (5)	0.3848 (4)	0.0394 (8)
H5A	0.6304	0.6094	0.2810	0.047*
H5B	0.6841	0.7330	0.3938	0.047*
C6	0.5817 (3)	0.6351 (5)	0.4589 (5)	0.0497 (10)
H6A	0.5542	0.5328	0.4524	0.060*
H6B	0.6065	0.6604	0.5621	0.060*
C7	0.0750 (4)	0.3876 (9)	0.9066 (8)	0.0911 (19)
H7A	0.0295	0.3351	0.9386	0.137*
H7B	0.0778	0.3444	0.8146	0.137*
H7C	0.0611	0.4968	0.8944	0.137*
H1	0.702 (4)	0.413 (3)	0.437 (6)	0.080*

	U11	U22	U33	U12	U13	U23
S1	0.0318 (6)	0.0445 (6)	0.0335 (6)	0.0004 (3)	0.0079 (4)	0.0002 (3)
O1	0.0618 (19)	0.0560 (18)	0.0355 (14)	−0.0019 (14)	0.0078 (13)	0.0054 (11)
O2	0.068 (2)	0.0439 (17)	0.0592 (18)	−0.0076 (14)	0.0246 (14)	−0.0018 (12)
O3	0.071 (2)	0.065 (2)	0.0364 (14)	0.0049 (15)	0.0159 (13)	−0.0076 (12)
O4	0.0357 (18)	0.089 (3)	0.107 (3)	0.0122 (15)	0.0190 (18)	0.005 (2)
O5	0.070 (3)	0.081 (3)	0.143 (4)	−0.002 (2)	−0.016 (3)	0.016 (3)
O6	0.0330 (15)	0.092 (2)	0.0519 (17)	0.0065 (15)	0.0046 (12)	−0.0012 (16)
N1	0.0305 (15)	0.0446 (17)	0.0346 (15)	−0.0036 (12)	0.0068 (11)	−0.0012 (12)
N2	0.0317 (16)	0.0509 (19)	0.0376 (15)	−0.0020 (12)	0.0085 (12)	−0.0046 (13)
C1	0.039 (2)	0.067 (3)	0.0326 (18)	0.0013 (18)	0.0064 (14)	0.0002 (16)
C2	0.043 (2)	0.089 (3)	0.039 (2)	0.009 (2)	0.0008 (17)	0.011 (2)
C3	0.036 (2)	0.081 (3)	0.050 (2)	0.0041 (19)	0.0122 (17)	−0.0046 (19)
C4	0.036 (2)	0.068 (3)	0.0380 (18)	−0.0050 (18)	0.0119 (15)	−0.0039 (16)
C5	0.0333 (18)	0.055 (2)	0.0287 (16)	0.0000 (15)	0.0072 (13)	−0.0001 (14)
C6	0.050 (2)	0.059 (2)	0.047 (2)	0.0108 (19)	0.0257 (17)	0.0136 (18)
C7	0.049 (3)	0.108 (5)	0.109 (5)	0.005 (3)	0.011 (3)	0.000 (4)

S1—O3	1.446 (3)	C1—H1A	0.9700
S1—O4	1.461 (4)	C1—H1B	0.9700
S1—O1	1.463 (3)	C2—H2D	0.9700
S1—O2	1.479 (3)	C2—H2E	0.9700
O5—C7	1.358 (7)	C3—C4	1.516 (6)
O5—H5	0.8200	C3—H3A	0.9700
O6—C3	1.405 (5)	C3—H3B	0.9700
O6—C2	1.409 (6)	C4—H4A	0.9700
N1—C5	1.497 (5)	C4—H4B	0.9700
N1—C4	1.508 (5)	C5—C6	1.512 (5)
N1—C1	1.509 (5)	C5—H5A	0.9700
N1—H1	0.899 (10)	C5—H5B	0.9700
N2—C6	1.466 (5)	C6—H6A	0.9700
N2—H2A	0.8900	C6—H6B	0.9700
N2—H2B	0.8900	C7—H7A	0.9600
N2—H2C	0.8900	C7—H7B	0.9600
C1—C2	1.524 (6)	C7—H7C	0.9600
O3—S1—O4	110.5 (2)	H2D—C2—H2E	108.0
O3—S1—O1	109.1 (2)	O6—C3—C4	111.5 (4)
O4—S1—O1	111.2 (2)	O6—C3—H3A	109.3
O3—S1—O2	109.6 (2)	C4—C3—H3A	109.3
O4—S1—O2	107.5 (2)	O6—C3—H3B	109.3
O1—S1—O2	108.85 (17)	C4—C3—H3B	109.3
C7—O5—H5	109.5	H3A—C3—H3B	108.0
C3—O6—C2	108.6 (3)	N1—C4—C3	111.3 (3)
C5—N1—C4	108.3 (3)	N1—C4—H4A	109.4
C5—N1—C1	113.0 (3)	C3—C4—H4A	109.4
C4—N1—C1	109.6 (3)	N1—C4—H4B	109.4
C5—N1—H1	112 (4)	C3—C4—H4B	109.4
C4—N1—H1	104 (4)	H4A—C4—H4B	108.0
C1—N1—H1	109 (4)	N1—C5—C6	111.7 (3)
C6—N2—H2A	109.5	N1—C5—H5A	109.3
C6—N2—H2B	109.5	C6—C5—H5A	109.3
H2A—N2—H2B	109.5	N1—C5—H5B	109.3
C6—N2—H2C	109.5	C6—C5—H5B	109.3
H2A—N2—H2C	109.5	H5A—C5—H5B	107.9
H2B—N2—H2C	109.5	N2—C6—C5	110.8 (3)
N1—C1—C2	109.6 (3)	N2—C6—H6A	109.5
N1—C1—H1A	109.7	C5—C6—H6A	109.5
C2—C1—H1A	109.7	N2—C6—H6B	109.5
N1—C1—H1B	109.7	C5—C6—H6B	109.5
C2—C1—H1B	109.7	H6A—C6—H6B	108.1
H1A—C1—H1B	108.2	O5—C7—H7A	109.5
O6—C2—C1	111.3 (4)	O5—C7—H7B	109.5
O6—C2—H2D	109.4	H7A—C7—H7B	109.5
C1—C2—H2D	109.4	O5—C7—H7C	109.5
O6—C2—H2E	109.4	H7A—C7—H7C	109.5
C1—C2—H2E	109.4	H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4i	0.82	1.85	2.659 (6)	172
O5—H5···S1i	0.82	2.92	3.636 (6)	147
N2—H2A···O1ii	0.89	2.07	2.914 (5)	158
N2—H2A···O3ii	0.89	2.30	3.001 (5)	135
N2—H2A···S1ii	0.89	2.68	3.553 (4)	167
N2—H2B···O2iii	0.89	2.02	2.898 (5)	168
N2—H2B···O3iii	0.89	2.45	3.081 (5)	128
N2—H2B···S1iii	0.89	2.72	3.567 (4)	160
N2—H2C···O2	0.89	2.18	2.997 (5)	153
N2—H2C···O1	0.89	2.23	2.930 (4)	135
N2—H2C···S1	0.89	2.71	3.565 (4)	162
N1—H1···O2iv	0.90 (1)	2.01 (3)	2.837 (5)	152 (5)
N1—H1···O4iv	0.90 (1)	2.60 (3)	3.382 (6)	146 (5)
N1—H1···S1iv	0.90 (1)	2.85 (1)	3.738 (4)	172 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O4i	0.82	1.85	2.659 (6)	172
O5—H5⋯S1i	0.82	2.92	3.636 (6)	147
N2—H2A⋯O1ii	0.89	2.07	2.914 (5)	158
N2—H2A⋯O3ii	0.89	2.30	3.001 (5)	135
N2—H2A⋯S1ii	0.89	2.68	3.553 (4)	167
N2—H2B⋯O2iii	0.89	2.02	2.898 (5)	168
N2—H2B⋯O3iii	0.89	2.45	3.081 (5)	128
N2—H2B⋯S1iii	0.89	2.72	3.567 (4)	160
N2—H2C⋯O2	0.89	2.18	2.997 (5)	153
N2—H2C⋯O1	0.89	2.23	2.930 (4)	135
N2—H2C⋯S1	0.89	2.71	3.565 (4)	162
N1—H1⋯O2iv	0.90 (1)	2.01 (3)	2.837 (5)	152 (5)
N1—H1⋯O4iv	0.90 (1)	2.60 (3)	3.382 (6)	146 (5)
N1—H1⋯S1iv	0.90 (1)	2.85 (1)	3.738 (4)	172 (5)

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