Bis(3-amino-propan-1-aminium) naphthalene-1,5-disulfonate dihydrate.

In the title hydrated salt, 2C(3)H(11)N(2) (+)·C(10)H(6)O(6)S(2) (2-)·2H(2)O, the anion lies on a center of inversion; its sulfonate -SO(3) group features one S-O bond that is longer than the other two. The O atom of this longer bond is the hydrogen-bond acceptor to the amino H atom of one cation and the ammonium H atom of another cation. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the cations, anions and water mol-ecules into a three-dimensional network.

Related literature

For a related structure, see: Gao & Ng (2012 ▶).

Experimental

Crystal data

2C3H11N2 +·C10H6O6S2 2−·2H2O

M = 472.58

Triclinic,

a = 8.0913 (16) Å

b = 8.1917 (16) Å

c = 9.8062 (18) Å

α = 71.182 (5)°

β = 65.950 (5)°

γ = 79.945 (5)°

V = 561.12 (19) Å3

Z = 1

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.21 × 0.17 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.942, T max = 0.953

5584 measured reflections

2552 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.05

2552 reflections

165 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.39 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018296/xu5521sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018296/xu5521Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018296/xu5521Isup3.cml

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

2C3H11N2+·C10H6O6S22−·2H2O	Z = 1
Mr = 472.58	F(000) = 252
Triclinic, P1	Dx = 1.399 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0913 (16) Å	Cell parameters from 3803 reflections
b = 8.1917 (16) Å	θ = 3.0–27.5°
c = 9.8062 (18) Å	µ = 0.29 mm−1
α = 71.182 (5)°	T = 293 K
β = 65.950 (5)°	Prism, colorless
γ = 79.945 (5)°	0.21 × 0.17 × 0.17 mm
V = 561.12 (19) Å3

Rigaku R-AXIS RAPID IP diffractometer	2552 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scan	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→9
Tmin = 0.942, Tmax = 0.953	k = −10→10
5584 measured reflections	l = −12→12

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.1592P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2552 reflections	Δρmax = 0.44 e Å−3
165 parameters	Δρmin = −0.39 e Å−3
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (12)

	x	y	z	Uiso*/Ueq
S1	0.27701 (5)	0.72860 (5)	0.28439 (4)	0.02880 (18)
O1	0.40860 (17)	0.78029 (17)	0.12668 (14)	0.0406 (3)
O2	0.35741 (17)	0.62846 (16)	0.39549 (15)	0.0402 (3)
O3	0.12666 (17)	0.64501 (17)	0.29413 (17)	0.0425 (3)
O1W	0.75757 (19)	0.63049 (19)	0.10446 (16)	0.0421 (3)
H1W1	0.6524 (18)	0.661 (3)	0.106 (3)	0.057 (7)*
H1W2	0.766 (4)	0.5307 (17)	0.096 (3)	0.063 (8)*
N1	0.8221 (3)	0.3040 (2)	0.0702 (2)	0.0437 (4)
H11	0.9387 (16)	0.288 (3)	0.053 (3)	0.063 (8)*
H12	0.792 (4)	0.294 (4)	−0.003 (2)	0.067 (8)*
N2	0.7492 (2)	−0.3142 (2)	0.36576 (18)	0.0367 (4)
H21	0.744 (3)	−0.340 (3)	0.287 (2)	0.059 (7)*
H22	0.701 (3)	−0.400 (3)	0.450 (2)	0.065 (7)*
H23	0.8614 (16)	−0.323 (3)	0.361 (3)	0.046 (6)*
C1	0.1830 (2)	0.9236 (2)	0.33721 (18)	0.0269 (3)
C2	0.2538 (2)	1.0749 (2)	0.23475 (18)	0.0320 (4)
H2	0.3496	1.0745	0.1411	0.038*
C3	0.1822 (2)	1.2322 (2)	0.27039 (19)	0.0341 (4)
H3	0.2318	1.3352	0.2003	0.041*
C4	0.0411 (2)	1.2350 (2)	0.40653 (18)	0.0297 (4)
H4A	−0.0057	1.3403	0.4274	0.036*
C5	−0.03570 (19)	1.08034 (19)	0.51689 (17)	0.0251 (3)
C6	0.7250 (3)	0.1771 (2)	0.2140 (2)	0.0387 (4)
H6A	0.5962	0.1970	0.2356	0.046*
H6B	0.7462	0.1951	0.2985	0.046*
C7	0.7781 (3)	−0.0097 (2)	0.2119 (2)	0.0385 (4)
H7A	0.7530	−0.0300	0.1302	0.046*
H7B	0.9073	−0.0301	0.1882	0.046*
C8	0.6774 (2)	−0.1352 (2)	0.3650 (2)	0.0360 (4)
H8A	0.6896	−0.1063	0.4488	0.043*
H8B	0.5496	−0.1262	0.3825	0.043*

	U11	U22	U33	U12	U13	U23
S1	0.0281 (3)	0.0244 (2)	0.0307 (3)	−0.00188 (15)	−0.00813 (18)	−0.00714 (17)
O1	0.0406 (7)	0.0360 (7)	0.0315 (6)	0.0011 (5)	−0.0028 (5)	−0.0076 (5)
O2	0.0405 (7)	0.0329 (7)	0.0413 (7)	0.0000 (5)	−0.0168 (6)	−0.0019 (5)
O3	0.0366 (7)	0.0390 (7)	0.0580 (8)	−0.0049 (5)	−0.0135 (6)	−0.0256 (6)
O1W	0.0412 (7)	0.0395 (8)	0.0456 (8)	0.0018 (6)	−0.0141 (6)	−0.0169 (6)
N1	0.0528 (10)	0.0322 (8)	0.0420 (9)	−0.0036 (7)	−0.0147 (8)	−0.0085 (7)
N2	0.0376 (8)	0.0327 (8)	0.0368 (8)	−0.0065 (6)	−0.0146 (7)	−0.0028 (6)
C1	0.0298 (7)	0.0245 (8)	0.0278 (7)	−0.0035 (6)	−0.0122 (6)	−0.0063 (6)
C2	0.0339 (8)	0.0307 (9)	0.0262 (7)	−0.0073 (6)	−0.0066 (6)	−0.0047 (6)
C3	0.0418 (9)	0.0238 (8)	0.0311 (8)	−0.0107 (7)	−0.0097 (7)	−0.0011 (6)
C4	0.0368 (8)	0.0210 (8)	0.0297 (8)	−0.0063 (6)	−0.0110 (7)	−0.0043 (6)
C5	0.0273 (7)	0.0233 (8)	0.0265 (7)	−0.0050 (6)	−0.0123 (6)	−0.0046 (6)
C6	0.0396 (9)	0.0340 (9)	0.0424 (9)	−0.0042 (7)	−0.0133 (8)	−0.0123 (8)
C7	0.0425 (9)	0.0321 (9)	0.0390 (9)	−0.0020 (7)	−0.0143 (8)	−0.0087 (7)
C8	0.0337 (8)	0.0347 (9)	0.0395 (9)	−0.0041 (7)	−0.0125 (7)	−0.0106 (7)

S1—O1	1.4484 (13)	C2—H2	0.9300
S1—O2	1.4484 (13)	C3—C4	1.362 (2)
S1—O3	1.4532 (13)	C3—H3	0.9300
S1—C1	1.7848 (16)	C4—C5	1.416 (2)
O1W—H1W1	0.840 (10)	C4—H4A	0.9300
O1W—H1W2	0.837 (10)	C5—C5i	1.427 (3)
N1—C6	1.457 (2)	C5—C1i	1.436 (2)
N1—H11	0.883 (10)	C6—C7	1.520 (2)
N1—H12	0.879 (10)	C6—H6A	0.9700
N2—C8	1.479 (2)	C6—H6B	0.9700
N2—H21	0.886 (10)	C7—C8	1.508 (2)
N2—H22	0.885 (10)	C7—H7A	0.9700
N2—H23	0.881 (9)	C7—H7B	0.9700
C1—C2	1.360 (2)	C8—H8A	0.9700
C1—C5i	1.436 (2)	C8—H8B	0.9700
C2—C3	1.408 (2)
O1—S1—O2	113.11 (8)	C3—C4—C5	121.11 (15)
O1—S1—O3	111.96 (8)	C3—C4—H4A	119.4
O2—S1—O3	112.63 (8)	C5—C4—H4A	119.4
O1—S1—C1	106.07 (7)	C4—C5—C5i	119.01 (17)
O2—S1—C1	106.32 (8)	C4—C5—C1i	123.18 (14)
O3—S1—C1	106.10 (7)	C5i—C5—C1i	117.81 (16)
H1W1—O1W—H1W2	100 (2)	N1—C6—C7	114.59 (16)
C6—N1—H11	108.1 (17)	N1—C6—H6A	108.6
C6—N1—H12	107.7 (18)	C7—C6—H6A	108.6
H11—N1—H12	115 (3)	N1—C6—H6B	108.6
C8—N2—H21	110.4 (16)	C7—C6—H6B	108.6
C8—N2—H22	119.3 (18)	H6A—C6—H6B	107.6
H21—N2—H22	107 (2)	C8—C7—C6	112.28 (15)
C8—N2—H23	108.1 (15)	C8—C7—H7A	109.1
H21—N2—H23	111 (2)	C6—C7—H7A	109.1
H22—N2—H23	101 (2)	C8—C7—H7B	109.1
C2—C1—C5i	121.35 (15)	C6—C7—H7B	109.1
C2—C1—S1	118.04 (13)	H7A—C7—H7B	107.9
C5i—C1—S1	120.60 (12)	N2—C8—C7	110.76 (14)
C1—C2—C3	120.06 (15)	N2—C8—H8A	109.5
C1—C2—H2	120.0	C7—C8—H8A	109.5
C3—C2—H2	120.0	N2—C8—H8B	109.5
C4—C3—C2	120.65 (15)	C7—C8—H8B	109.5
C4—C3—H3	119.7	H8A—C8—H8B	108.1
C2—C3—H3	119.7
O1—S1—C1—C2	−4.68 (15)	S1—C1—C2—C3	179.05 (12)
O2—S1—C1—C2	115.97 (14)	C1—C2—C3—C4	−0.5 (3)
O3—S1—C1—C2	−123.91 (14)	C2—C3—C4—C5	1.0 (3)
O1—S1—C1—C5i	174.63 (12)	C3—C4—C5—C5i	−0.7 (3)
O2—S1—C1—C5i	−64.71 (14)	C3—C4—C5—C1i	179.21 (15)
O3—S1—C1—C5i	55.41 (14)	N1—C6—C7—C8	178.34 (16)
C5i—C1—C2—C3	−0.3 (2)	C6—C7—C8—N2	−172.59 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O1	0.84 (1)	2.00 (1)	2.826 (2)	166 (3)
O1w—H1w2···N1	0.84 (1)	1.91 (1)	2.736 (2)	172 (3)
N1—H12···O3ii	0.88 (1)	2.55 (2)	3.317 (2)	147 (2)
N2—H21···O1wiii	0.89 (1)	1.84 (1)	2.715 (2)	172 (2)
N2—H22···O2iv	0.89 (1)	1.98 (1)	2.845 (2)	165 (3)
N2—H23···O3v	0.88 (1)	1.97 (1)	2.825 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w1⋯O1	0.84 (1)	2.00 (1)	2.826 (2)	166 (3)
O1w—H1w2⋯N1	0.84 (1)	1.91 (1)	2.736 (2)	172 (3)
N1—H12⋯O3i	0.88 (1)	2.55 (2)	3.317 (2)	147 (2)
N2—H21⋯O1wii	0.89 (1)	1.84 (1)	2.715 (2)	172 (2)
N2—H22⋯O2iii	0.89 (1)	1.98 (1)	2.845 (2)	165 (3)
N2—H23⋯O3iv	0.88 (1)	1.97 (1)	2.825 (2)	164 (2)

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