Bis(di-cyclo-hexyl-ammonium) sulfate dihydrate.

In the title dihydrate salt, 2C12H24N(+)·SO4 (2-)·2H2O, the cation possesses twofold rotational symmetry, with the N atom situated on the twofold axis. The sulfate anion has fourfold roto-inversion symmetry, with the S atom located on the -4 axis. In the crystal, the components are linked via ammonium-sulfate N-H⋯O and water-sulfate O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the structure of tri­ammonium hydrogen di­sulfate, see: Suzuki & Makita (1978 ▶). For various sulfate complexes, see: Hathaway (1973 ▶); Diassé-Sarr et al. (1997 ▶); Diallo et al. (2010 ▶); Diop et al. (2012 ▶).

Experimental

Crystal data

2C12H24N+·SO4 2−·2H2O

M = 496.74

Tetragonal,

a = 12.437 (3) Å

c = 17.290 (4) Å

V = 2674.4 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.48 × 0.44 × 0.37 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

9860 measured reflections

1191 independent reflections

1131 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.075

S = 1.16

1191 reflections

84 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.12 e Å−3

Absolute structure: Flack (1983 ▶); 514 Friedel pairs

Absolute structure parameter: 0.04 (10)

Data collection: locally modified CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: SET4 (de Boer & Duisenberg, 1984 ▶); data reduction: HELENA (Spek, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814000968/pk2513sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000968/pk2513Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000968/pk2513Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

2C12H24N+·SO42−·2H2O	Dx = 1.234 Mg m−3
Mr = 496.74	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I42d	Cell parameters from 5803 reflections
Hall symbol: I -4 2bw	θ = 3.3–25.0°
a = 12.437 (3) Å	µ = 0.16 mm−1
c = 17.290 (4) Å	T = 293 K
V = 2674.4 (11) Å3	Prism, colourless
Z = 4	0.48 × 0.44 × 0.37 mm
F(000) = 1096

Bruker APEXII CCD area-detector diffractometer	1131 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −14→14
9860 measured reflections	k = −14→14
1191 independent reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.6142P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
1191 reflections	Δρmax = 0.16 e Å−3
84 parameters	Δρmin = −0.12 e Å−3
0 restraints	Absolute structure: Flack (1983); 514 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (10)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1	0.10093 (14)	0.25000	0.12500	0.0327 (5)
C1	0.08284 (13)	0.36633 (14)	0.01210 (9)	0.0436 (5)
C2	0.14068 (15)	0.43411 (15)	−0.04852 (10)	0.0503 (6)
C3	0.21449 (14)	0.51624 (14)	−0.01157 (10)	0.0492 (5)
C4	0.29313 (14)	0.46346 (14)	0.04327 (11)	0.0493 (5)
C5	0.23596 (13)	0.39552 (13)	0.10417 (9)	0.0414 (5)
C6	0.16348 (12)	0.31304 (12)	0.06577 (8)	0.0330 (4)
S1	0.00000	0.00000	0.00000	0.0307 (1)
O1	−0.02822 (9)	0.09357 (10)	0.04872 (7)	0.0507 (4)
O1W	−0.1807 (2)	0.25000	0.12500	0.1049 (13)
H1A	0.03480	0.41170	0.04200	0.0520*
H1N	0.0568 (15)	0.2011 (15)	0.0997 (10)	0.045 (5)*
H2A	0.18250	0.38740	−0.08190	0.0600*
H2B	0.08790	0.47090	−0.08030	0.0600*
H3A	0.25390	0.55400	−0.05160	0.0590*
H3B	0.17180	0.56860	0.01650	0.0590*
H4A	0.33540	0.51850	0.06880	0.0590*
H4B	0.34190	0.41820	0.01400	0.0590*
H5A	0.28880	0.35910	0.13600	0.0500*
H5B	0.19330	0.44170	0.13740	0.0500*
H6	0.20800	0.26330	0.03570	0.0400*
H21B	0.03990	0.31170	−0.01340	0.0520*
H1W	−0.143 (3)	0.203 (3)	0.093 (2)	0.1570*

	U11	U22	U33	U12	U13	U23
N1	0.0290 (9)	0.0315 (9)	0.0377 (9)	0.0000	0.0000	−0.0034 (8)
C1	0.0397 (8)	0.0456 (9)	0.0454 (9)	−0.0032 (7)	−0.0098 (7)	0.0033 (7)
C2	0.0534 (11)	0.0556 (11)	0.0419 (8)	−0.0025 (8)	−0.0062 (8)	0.0093 (8)
C3	0.0541 (10)	0.0414 (9)	0.0520 (9)	−0.0032 (7)	0.0021 (8)	0.0081 (8)
C4	0.0415 (9)	0.0496 (10)	0.0567 (9)	−0.0107 (7)	−0.0021 (8)	0.0092 (8)
C5	0.0369 (8)	0.0453 (9)	0.0419 (8)	−0.0076 (7)	−0.0062 (7)	0.0042 (7)
C6	0.0322 (7)	0.0320 (7)	0.0348 (7)	0.0015 (6)	0.0011 (6)	−0.0006 (6)
S1	0.0294 (2)	0.0294 (2)	0.0332 (3)	0.0000	0.0000	0.0000
O1	0.0526 (8)	0.0448 (7)	0.0546 (6)	−0.0044 (5)	0.0049 (5)	−0.0205 (6)
O1W	0.0498 (14)	0.109 (2)	0.156 (3)	0.0000	0.0000	−0.003 (2)

S1—O1i	1.4789 (13)	C4—C5	1.526 (2)
S1—O1ii	1.4789 (13)	C5—C6	1.518 (2)
S1—O1iii	1.4789 (13)	C1—H21B	0.9700
S1—O1	1.4789 (13)	C1—H1A	0.9700
O1W—H1Wiv	0.93 (4)	C2—H2B	0.9700
O1W—H1W	0.93 (4)	C2—H2A	0.9700
N1—C6iv	1.5062 (17)	C3—H3A	0.9700
N1—C6	1.5062 (17)	C3—H3B	0.9700
N1—H1N	0.929 (18)	C4—H4A	0.9700
N1—H1Niv	0.929 (18)	C4—H4B	0.9700
C1—C6	1.519 (2)	C5—H5B	0.9700
C1—C2	1.525 (2)	C5—H5A	0.9700
C2—C3	1.515 (3)	C6—H6	0.9800
C3—C4	1.512 (3)
O1i—S1—O1iii	110.56 (7)	C6—C1—H1A	110.00
O1ii—S1—O1iii	108.93 (6)	C1—C2—H2A	109.00
O1—S1—O1ii	110.56 (7)	C1—C2—H2B	109.00
O1—S1—O1iii	108.93 (6)	C3—C2—H2A	109.00
O1—S1—O1i	108.93 (6)	C3—C2—H2B	109.00
O1i—S1—O1ii	108.93 (6)	H2A—C2—H2B	108.00
H1W—O1W—H1Wiv	120 (3)	C2—C3—H3A	109.00
C6—N1—C6iv	117.81 (14)	C2—C3—H3B	109.00
C6—N1—H1Niv	106.5 (11)	C4—C3—H3A	109.00
C6—N1—H1N	109.0 (11)	C4—C3—H3B	109.00
C6iv—N1—H1N	106.5 (11)	H3A—C3—H3B	108.00
H1N—N1—H1Niv	107.6 (16)	H4A—C4—H4B	108.00
C6iv—N1—H1Niv	109.0 (11)	C3—C4—H4A	109.00
C2—C1—C6	110.46 (13)	C3—C4—H4B	109.00
C1—C2—C3	111.64 (14)	C5—C4—H4A	109.00
C2—C3—C4	111.33 (15)	C5—C4—H4B	109.00
C3—C4—C5	111.82 (14)	C4—C5—H5A	110.00
C4—C5—C6	110.43 (13)	C4—C5—H5B	110.00
N1—C6—C5	111.16 (11)	C6—C5—H5A	110.00
C1—C6—C5	111.37 (13)	C6—C5—H5B	110.00
N1—C6—C1	107.55 (12)	H5A—C5—H5B	108.00
H1A—C1—H21B	108.00	N1—C6—H6	109.00
C6—C1—H21B	110.00	C1—C6—H6	109.00
C2—C1—H1A	110.00	C5—C6—H6	109.00
C2—C1—H21B	110.00
C6iv—N1—C6—C1	178.50 (10)	C1—C2—C3—C4	54.74 (19)
C6iv—N1—C6—C5	−59.34 (14)	C2—C3—C4—C5	−54.68 (19)
C6—C1—C2—C3	−55.56 (19)	C3—C4—C5—C6	55.35 (18)
C2—C1—C6—N1	178.63 (12)	C4—C5—C6—N1	−176.33 (12)
C2—C1—C6—C5	56.60 (17)	C4—C5—C6—C1	−56.41 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.929 (18)	1.919 (19)	2.8468 (17)	176.6 (16)
O1W—H1W···O1	0.93 (4)	2.12 (4)	3.020 (2)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.929 (18)	1.919 (19)	2.8468 (17)	176.6 (16)
O1W—H1W⋯O1	0.93 (4)	2.12 (4)	3.020 (2)	163 (3)