1,3-Diammonio-1,2,3-tride-oxy-cis-inositol sulfate.

In the crystal structure of the title compound, C(6)H(16)N(2)O(3) (2+)·SO(4) (2-), each cation forms three O-H⋯O and five N-H⋯O hydrogen bonds to six neighbouring sulfate anions. In addition, interlinking of the cations by N-H⋯O interactions is also observed. The cyclo-hexane ring adopts a chair conformation with two axial hy-droxy groups. Although the separation of 2.928 Å is almost ideal for a hydrogen bond, intra-molecular hydrogen bonding between these two hy-droxy groups is not observed.

Related literature

The synthesis of the chloride salt, as well as formation of a CuII complex of 1,3-diamino-1,2,3-tride­oxy-cis-inositol, was reported by Merten et al. (2012 ▶). A crystal structure deter­min­ation of the chloride salt was performed by Neis et al. (2012 ▶). The importance of intra­molecular hydrogen bonding in syn-1,3,5-tris­ubstituted cyclo­hexane derivatives has been discussed by Gencheva et al. (2000 ▶), Kramer et al. (1998 ▶), Kuppert et al. (2006 ▶), and Neis et al. (2010 ▶). Puckering parameters were calculated according to Cremer & Pople (1975 ▶). For the treatment of hydrogen atoms in SHELXL, see: Müller et al. (2006 ▶).

Experimental

Crystal data

C6H16N2O3 2+·SO4 2−

M = 260.27

Monoclinic,

a = 9.2151 (18) Å

b = 6.6673 (13) Å

c = 17.267 (4) Å

β = 101.46 (3)°

V = 1039.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 200 K

0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS image plate diffractometer

6961 measured reflections

1779 independent reflections

1685 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.066

S = 1.06

1779 reflections

172 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: IPDS Software (Stoe & Cie, 1997 ▶); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016029/bx2402sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016029/bx2402Isup2.hkl

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

C6H16N2O32+·SO42−	F(000) = 552
Mr = 260.27	Dx = 1.663 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3837 reflections
a = 9.2151 (18) Å	θ = 2.6–25.0°
b = 6.6673 (13) Å	µ = 0.34 mm−1
c = 17.267 (4) Å	T = 200 K
β = 101.46 (3)°	Prism, colourless
V = 1039.7 (4) Å3	0.30 × 0.20 × 0.15 mm
Z = 4

Stoe IPDS image plate diffractometer	1685 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
phi scans	h = −10→10
6961 measured reflections	k = −7→7
1779 independent reflections	l = −20→20

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0259P)2 + 0.7072P] where P = (Fo2 + 2Fc2)/3
1779 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.27 e Å−3
9 restraints	Δρmin = −0.29 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
C5	0.44604 (15)	−0.0876 (2)	0.10574 (8)	0.0129 (3)
H5	0.4373	−0.1399	0.0507	0.015*
C6	0.35712 (15)	−0.2238 (2)	0.15088 (8)	0.0149 (3)
H6A	0.3961	−0.3624	0.1521	0.018*
H6B	0.3684	−0.1762	0.2061	0.018*
C2	0.12716 (15)	−0.0111 (2)	0.10691 (8)	0.0139 (3)
H2	0.0241	−0.0171	0.0749	0.017*
C1	0.19415 (15)	−0.2228 (2)	0.11143 (8)	0.0136 (3)
H1	0.1839	−0.2768	0.0566	0.016*
C3	0.22081 (16)	0.1251 (2)	0.06417 (8)	0.0137 (3)
H3	0.2117	0.0722	0.0092	0.016*
C4	0.38668 (15)	0.1297 (2)	0.10194 (8)	0.0126 (3)
H4	0.4396	0.2105	0.0674	0.015*
N1	0.11358 (15)	−0.3591 (2)	0.15750 (8)	0.0171 (3)
H1A	0.124 (2)	−0.325 (3)	0.2070 (9)	0.026*
H1B	0.142 (2)	−0.481 (2)	0.1514 (10)	0.026*
H1C	0.0204 (17)	−0.360 (3)	0.1393 (10)	0.026*
N5	0.60555 (14)	−0.09248 (19)	0.14663 (8)	0.0151 (3)
H5A	0.6514 (19)	0.006 (3)	0.1269 (10)	0.023*
H5B	0.612 (2)	−0.084 (3)	0.1971 (9)	0.023*
H5C	0.642 (2)	−0.208 (2)	0.1385 (10)	0.023*
O4	0.41236 (12)	0.21890 (16)	0.17886 (6)	0.0177 (2)
H4O	0.4859 (19)	0.294 (3)	0.1786 (11)	0.027*
O2	0.12055 (12)	0.05338 (16)	0.18490 (6)	0.0188 (2)
H2O	0.0491 (19)	0.137 (3)	0.1815 (11)	0.028*
O3	0.15853 (12)	0.32218 (16)	0.05817 (6)	0.0206 (2)
H3O	0.171 (2)	0.369 (3)	0.0137 (9)	0.031*
S1	0.77047 (4)	0.40360 (5)	0.132375 (19)	0.01264 (13)
O7	0.80382 (13)	0.58885 (16)	0.09000 (6)	0.0268 (3)
O8	0.90424 (11)	0.34825 (16)	0.19086 (6)	0.0201 (2)
O5	0.72807 (12)	0.23732 (16)	0.07600 (6)	0.0221 (3)
O6	0.65015 (12)	0.45266 (18)	0.17466 (7)	0.0294 (3)

	U11	U22	U33	U12	U13	U23
C5	0.0114 (7)	0.0124 (7)	0.0148 (7)	−0.0003 (5)	0.0022 (5)	−0.0010 (5)
C6	0.0148 (7)	0.0096 (7)	0.0200 (7)	−0.0004 (5)	0.0027 (5)	0.0025 (5)
C2	0.0112 (7)	0.0156 (7)	0.0142 (6)	0.0004 (5)	0.0008 (5)	−0.0008 (5)
C1	0.0151 (7)	0.0118 (7)	0.0146 (6)	−0.0038 (5)	0.0043 (5)	−0.0007 (5)
C3	0.0165 (7)	0.0106 (7)	0.0137 (6)	0.0026 (5)	0.0024 (5)	0.0004 (5)
C4	0.0150 (7)	0.0104 (7)	0.0131 (6)	−0.0017 (5)	0.0044 (5)	−0.0001 (5)
N1	0.0178 (7)	0.0142 (6)	0.0205 (7)	−0.0052 (5)	0.0067 (5)	−0.0017 (5)
N5	0.0129 (6)	0.0132 (6)	0.0191 (6)	0.0008 (5)	0.0032 (5)	−0.0012 (5)
O4	0.0199 (5)	0.0158 (5)	0.0179 (5)	−0.0065 (4)	0.0045 (4)	−0.0047 (4)
O2	0.0209 (6)	0.0195 (5)	0.0172 (5)	0.0050 (4)	0.0069 (4)	−0.0003 (4)
O3	0.0269 (6)	0.0136 (5)	0.0223 (5)	0.0083 (4)	0.0073 (4)	0.0046 (4)
S1	0.0110 (2)	0.01085 (19)	0.0156 (2)	−0.00160 (12)	0.00125 (13)	0.00023 (12)
O7	0.0345 (7)	0.0183 (6)	0.0244 (6)	−0.0064 (5)	−0.0017 (5)	0.0082 (4)
O8	0.0183 (5)	0.0207 (5)	0.0193 (5)	0.0035 (4)	−0.0009 (4)	0.0023 (4)
O5	0.0255 (6)	0.0209 (6)	0.0205 (5)	−0.0077 (4)	0.0055 (4)	−0.0057 (4)
O6	0.0168 (6)	0.0289 (6)	0.0455 (7)	−0.0041 (5)	0.0134 (5)	−0.0149 (5)

C5—N5	1.4993 (18)	C4—O4	1.4312 (17)
C5—C6	1.5355 (19)	C4—H4	1.0000
C5—C4	1.5454 (19)	N1—H1A	0.870 (14)
C5—H5	1.0000	N1—H1B	0.867 (15)
C6—C1	1.521 (2)	N1—H1C	0.853 (15)
C6—H6A	0.9900	N5—H5A	0.885 (15)
C6—H6B	0.9900	N5—H5B	0.864 (14)
C2—O2	1.4265 (17)	N5—H5C	0.866 (15)
C2—C1	1.536 (2)	O4—H4O	0.845 (15)
C2—C3	1.5386 (19)	O2—H2O	0.855 (15)
C2—H2	1.0000	O3—H3O	0.856 (15)
C1—N1	1.4985 (18)	S1—O5	1.4758 (11)
C1—H1	1.0000	S1—O8	1.4768 (11)
C3—O3	1.4297 (17)	S1—O6	1.4802 (12)
C3—C4	1.538 (2)	S1—O7	1.4982 (11)
C3—H3	1.0000
N5—C5—C6	108.67 (11)	C2—C3—H3	107.4
N5—C5—C4	110.25 (11)	O4—C4—C3	111.66 (11)
C6—C5—C4	110.85 (11)	O4—C4—C5	110.99 (11)
N5—C5—H5	109.0	C3—C4—C5	108.20 (11)
C6—C5—H5	109.0	O4—C4—H4	108.6
C4—C5—H5	109.0	C3—C4—H4	108.6
C1—C6—C5	110.43 (11)	C5—C4—H4	108.6
C1—C6—H6A	109.6	C1—N1—H1A	113.0 (13)
C5—C6—H6A	109.6	C1—N1—H1B	108.2 (12)
C1—C6—H6B	109.6	H1A—N1—H1B	112.8 (17)
C5—C6—H6B	109.6	C1—N1—H1C	112.2 (13)
H6A—C6—H6B	108.1	H1A—N1—H1C	105.8 (18)
O2—C2—C1	108.74 (11)	H1B—N1—H1C	104.5 (18)
O2—C2—C3	114.09 (11)	C5—N5—H5A	107.5 (12)
C1—C2—C3	107.97 (11)	C5—N5—H5B	109.5 (12)
O2—C2—H2	108.6	H5A—N5—H5B	113.7 (16)
C1—C2—H2	108.6	C5—N5—H5C	108.8 (12)
C3—C2—H2	108.6	H5A—N5—H5C	111.5 (17)
N1—C1—C6	107.99 (11)	H5B—N5—H5C	105.7 (17)
N1—C1—C2	110.35 (12)	C4—O4—H4O	103.2 (12)
C6—C1—C2	112.20 (11)	C2—O2—H2O	107.9 (12)
N1—C1—H1	108.7	C3—O3—H3O	106.1 (13)
C6—C1—H1	108.7	O5—S1—O8	109.81 (7)
C2—C1—H1	108.7	O5—S1—O6	111.42 (6)
O3—C3—C4	111.27 (11)	O8—S1—O6	108.86 (7)
O3—C3—C2	108.78 (11)	O5—S1—O7	110.50 (6)
C4—C3—C2	114.41 (11)	O8—S1—O7	108.39 (6)
O3—C3—H3	107.4	O6—S1—O7	107.77 (7)
C4—C3—H3	107.4
N5—C5—C6—C1	179.85 (11)	O2—C2—C3—C4	65.11 (15)
C4—C5—C6—C1	58.54 (15)	C1—C2—C3—C4	−55.89 (14)
C5—C6—C1—N1	179.52 (11)	O3—C3—C4—O4	58.04 (15)
C5—C6—C1—C2	−58.64 (15)	C2—C3—C4—O4	−65.75 (15)
O2—C2—C1—N1	51.84 (14)	O3—C3—C4—C5	−179.54 (11)
C3—C2—C1—N1	176.11 (10)	C2—C3—C4—C5	56.67 (15)
O2—C2—C1—C6	−68.64 (14)	N5—C5—C4—O4	−53.77 (15)
C3—C2—C1—C6	55.63 (14)	C6—C5—C4—O4	66.61 (14)
O2—C2—C3—O3	−60.00 (15)	N5—C5—C4—C3	−176.61 (11)
C1—C2—C3—O3	179.00 (10)	C6—C5—C4—C3	−56.23 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.87 (1)	2.09 (2)	2.9292 (17)	163 (2)
N1—H1B···O3ii	0.87 (2)	2.11 (2)	2.8125 (18)	138 (2)
N1—H1C···O7iii	0.85 (2)	2.04 (2)	2.882 (2)	170 (2)
N5—H5A···O5	0.89 (2)	1.97 (2)	2.8538 (17)	173 (2)
N5—H5B···O8iv	0.86 (1)	2.02 (2)	2.8530 (18)	162 (2)
N5—H5C···O7ii	0.87 (2)	2.29 (2)	3.0852 (18)	153 (2)
N5—H5C···O6ii	0.87 (2)	2.34 (2)	3.0856 (19)	144 (2)
O4—H4O···O6	0.85 (2)	1.86 (2)	2.7017 (16)	177 (2)
O2—H2O···O8v	0.86 (2)	1.97 (2)	2.8161 (15)	170 (2)
O3—H3O···O7vi	0.86 (2)	1.87 (2)	2.7149 (16)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.87 (1)	2.09 (2)	2.9292 (17)	163 (2)
N1—H1B⋯O3ii	0.87 (2)	2.11 (2)	2.8125 (18)	138 (2)
N1—H1C⋯O7iii	0.85 (2)	2.04 (2)	2.882 (2)	170 (2)
N5—H5A⋯O5	0.89 (2)	1.97 (2)	2.8538 (17)	173 (2)
N5—H5B⋯O8iv	0.86 (1)	2.02 (2)	2.8530 (18)	162 (2)
N5—H5C⋯O7ii	0.87 (2)	2.29 (2)	3.0852 (18)	153 (2)
N5—H5C⋯O6ii	0.87 (2)	2.34 (2)	3.0856 (19)	144 (2)
O4—H4O⋯O6	0.85 (2)	1.86 (2)	2.7017 (16)	177 (2)
O2—H2O⋯O8v	0.86 (2)	1.97 (2)	2.8161 (15)	170 (2)
O3—H3O⋯O7vi	0.86 (2)	1.87 (2)	2.7149 (16)	167 (2)

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