Bis(butan-1-aminium) naphthalene-1,5-disulfonate.

In the title compound, 2C(4)H(12)N(+)·C(10)H(6)O(6)S(2) (2-), the anion lies on an inversion center, so the asymmetric unit contains half an anion and one cation which are linked by a strong N-H⋯O hydrogen bond. The crystal structure comprises discrete ions, which are linked into centrosymmetric R(4) (4)(12) loops by N-H⋯O inter-actions.

Related literature

For related structures, see: Jin (2011a ▶,b ▶, 2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

2C4H12N+·C10H6O6S2 2−

M = 434.56

Monoclinic,

a = 8.1532 (16) Å

b = 9.2582 (19) Å

c = 14.108 (5) Å

β = 108.02 (3)°

V = 1012.7 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.3 × 0.3 × 0.2 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.489, T max = 1.000

10171 measured reflections

2316 independent reflections

2039 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.094

S = 1.14

2316 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018880/bx2406sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018880/bx2406Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018880/bx2406Isup3.cml

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

2C4H12N+·C10H6O6S22−	F(000) = 464
Mr = 434.56	Dx = 1.425 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3450 reflections
a = 8.1532 (16) Å	θ = 6.2–55.3°
b = 9.2582 (19) Å	µ = 0.30 mm−1
c = 14.108 (5) Å	T = 293 K
β = 108.02 (3)°	Block, colourless
V = 1012.7 (5) Å3	0.3 × 0.3 × 0.2 mm
Z = 2

Rigaku Mercury CCD diffractometer	2316 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −10→10
Tmin = 0.489, Tmax = 1.000	k = −12→12
10171 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.4216P] where P = (Fo2 + 2Fc2)/3
2316 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.43 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
C1	0.2319 (2)	1.0297 (2)	0.69402 (14)	0.0364 (4)
H1D	0.2261	1.0939	0.7473	0.044*
H1E	0.2235	1.0880	0.6356	0.044*
C2	0.4015 (2)	0.95077 (19)	0.72490 (13)	0.0332 (4)
H2A	0.4062	0.8866	0.6714	0.040*
H2B	0.4085	0.8919	0.7829	0.040*
C3	0.5553 (3)	1.0519 (2)	0.74938 (15)	0.0405 (5)
H3A	0.5439	1.1157	0.6932	0.049*
H3B	0.5553	1.1112	0.8061	0.049*
C4	0.7256 (3)	0.9722 (3)	0.77313 (17)	0.0524 (6)
H4A	0.7286	0.9168	0.7161	0.079*
H4B	0.7376	0.9087	0.8286	0.079*
H4C	0.8186	1.0406	0.7896	0.079*
C5	0.2728 (2)	1.06642 (17)	0.97032 (12)	0.0253 (3)
H5	0.1617	1.0294	0.9555	0.030*
C6	0.41452 (18)	0.97062 (16)	0.98793 (11)	0.0198 (3)
C7	0.39614 (19)	0.81664 (16)	0.98343 (11)	0.0204 (3)
C8	0.5368 (2)	0.72878 (17)	1.00271 (12)	0.0259 (3)
H8	0.5228	0.6290	1.0009	0.031*
C9	0.2973 (2)	1.21166 (18)	0.97477 (13)	0.0286 (4)
H9	0.2025	1.2727	0.9627	0.034*
N1	0.0850 (2)	0.92591 (16)	0.67115 (11)	0.0338 (3)
H1A	0.0840	0.8815	0.7269	0.041*
H1B	−0.0136	0.9735	0.6455	0.041*
H1C	0.0971	0.8608	0.6274	0.041*
O1	0.09524 (16)	0.78595 (15)	0.85199 (9)	0.0380 (3)
O2	0.11042 (16)	0.77995 (14)	1.02545 (9)	0.0343 (3)
O3	0.21663 (16)	0.57911 (13)	0.95327 (10)	0.0353 (3)
S1	0.18812 (5)	0.73440 (4)	0.95082 (3)	0.02387 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0436 (11)	0.0273 (9)	0.0380 (10)	0.0057 (8)	0.0123 (8)	0.0024 (7)
C2	0.0409 (10)	0.0277 (9)	0.0313 (9)	0.0033 (7)	0.0118 (8)	−0.0002 (7)
C3	0.0491 (12)	0.0362 (10)	0.0351 (10)	−0.0046 (9)	0.0113 (9)	0.0010 (8)
C4	0.0407 (12)	0.0699 (16)	0.0470 (12)	−0.0053 (11)	0.0139 (10)	−0.0027 (11)
C5	0.0186 (7)	0.0255 (8)	0.0320 (8)	−0.0005 (6)	0.0078 (6)	0.0015 (6)
C6	0.0197 (7)	0.0203 (7)	0.0206 (7)	−0.0011 (6)	0.0081 (6)	0.0008 (5)
C7	0.0212 (7)	0.0202 (7)	0.0204 (7)	−0.0037 (6)	0.0073 (6)	0.0008 (6)
C8	0.0282 (8)	0.0166 (7)	0.0333 (8)	−0.0006 (6)	0.0101 (7)	0.0011 (6)
C9	0.0225 (8)	0.0235 (8)	0.0400 (9)	0.0052 (6)	0.0100 (7)	0.0025 (7)
N1	0.0363 (8)	0.0338 (8)	0.0320 (8)	0.0092 (6)	0.0116 (6)	0.0033 (6)
O1	0.0318 (7)	0.0443 (8)	0.0306 (7)	−0.0089 (6)	−0.0010 (5)	0.0079 (5)
O2	0.0315 (6)	0.0355 (7)	0.0417 (7)	−0.0059 (5)	0.0198 (6)	−0.0001 (5)
O3	0.0332 (7)	0.0219 (6)	0.0481 (8)	−0.0085 (5)	0.0084 (6)	−0.0019 (5)
S1	0.0220 (2)	0.0218 (2)	0.0267 (2)	−0.00585 (14)	0.00604 (15)	0.00118 (15)

C1—N1	1.491 (2)	C5—H5	0.9300
C1—C2	1.505 (3)	C6—C7	1.433 (2)
C1—H1D	0.9700	C6—C6i	1.436 (3)
C1—H1E	0.9700	C7—C8	1.363 (2)
C2—C3	1.517 (3)	C7—S1	1.7847 (15)
C2—H2A	0.9700	C8—C9i	1.403 (2)
C2—H2B	0.9700	C8—H8	0.9300
C3—C4	1.516 (3)	C9—C8i	1.403 (2)
C3—H3A	0.9700	C9—H9	0.9300
C3—H3B	0.9700	N1—H1A	0.8900
C4—H4A	0.9600	N1—H1B	0.8900
C4—H4B	0.9600	N1—H1C	0.8900
C4—H4C	0.9600	O1—S1	1.4464 (14)
C5—C9	1.358 (2)	O2—S1	1.4493 (13)
C5—C6	1.416 (2)	O3—S1	1.4550 (13)
N1—C1—C2	110.73 (15)	C6—C5—H5	119.6
N1—C1—H1D	109.5	C5—C6—C7	123.16 (14)
C2—C1—H1D	109.5	C5—C6—C6i	118.93 (17)
N1—C1—H1E	109.5	C7—C6—C6i	117.91 (17)
C2—C1—H1E	109.5	C8—C7—C6	120.99 (14)
H1D—C1—H1E	108.1	C8—C7—S1	118.08 (12)
C1—C2—C3	112.76 (16)	C6—C7—S1	120.93 (11)
C1—C2—H2A	109.0	C7—C8—C9i	120.22 (15)
C3—C2—H2A	109.0	C7—C8—H8	119.9
C1—C2—H2B	109.0	C9i—C8—H8	119.9
C3—C2—H2B	109.0	C5—C9—C8i	121.16 (15)
H2A—C2—H2B	107.8	C5—C9—H9	119.4
C4—C3—C2	112.72 (18)	C8i—C9—H9	119.4
C4—C3—H3A	109.0	C1—N1—H1A	109.5
C2—C3—H3A	109.0	C1—N1—H1B	109.5
C4—C3—H3B	109.0	H1A—N1—H1B	109.5
C2—C3—H3B	109.0	C1—N1—H1C	109.5
H3A—C3—H3B	107.8	H1A—N1—H1C	109.5
C3—C4—H4A	109.5	H1B—N1—H1C	109.5
C3—C4—H4B	109.5	O1—S1—O2	112.83 (9)
H4A—C4—H4B	109.5	O1—S1—O3	112.40 (8)
C3—C4—H4C	109.5	O2—S1—O3	111.89 (8)
H4A—C4—H4C	109.5	O1—S1—C7	106.27 (8)
H4B—C4—H4C	109.5	O2—S1—C7	106.42 (8)
C9—C5—C6	120.77 (15)	O3—S1—C7	106.46 (7)
C9—C5—H5	119.6
N1—C1—C2—C3	−179.79 (15)	S1—C7—C8—C9i	177.76 (13)
C1—C2—C3—C4	−175.79 (16)	C6—C5—C9—C8i	−0.3 (3)
C9—C5—C6—C7	−179.48 (15)	C8—C7—S1—O1	−119.32 (13)
C9—C5—C6—C6i	0.9 (3)	C6—C7—S1—O1	59.88 (14)
C5—C6—C7—C8	−178.83 (15)	C8—C7—S1—O2	120.19 (13)
C6i—C6—C7—C8	0.8 (3)	C6—C7—S1—O2	−60.61 (14)
C5—C6—C7—S1	2.0 (2)	C8—C7—S1—O3	0.70 (15)
C6i—C6—C7—S1	−178.37 (13)	C6—C7—S1—O3	179.90 (12)
C6—C7—C8—C9i	−1.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.89	1.95	2.840 (2)	177
N1—H1C···O2ii	0.89	1.97	2.857 (2)	177
N1—H1B···O3iii	0.89	2.05	2.911 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.89	1.95	2.840 (2)	177
N1—H1C⋯O2i	0.89	1.97	2.857 (2)	177
N1—H1B⋯O3ii	0.89	2.05	2.911 (2)	162

Symmetry codes: (i) ; (ii) .