Bis(trimethyl-ammonium) naphthalene-1,5-disulfonate.

The asymmetric unit of the title compound, 2C(3)H(10)N(+)·C(10)H(6)S(2)O(6) (2-), contains a half-anion, which is completed by inversion symmetry, and one cation. The cations and anions are associated via strong N-H⋯O(sulfonate) hydrogen-bonding inter-actions, forming cation-anion-cation groups. Secondary inter-actions such as C-H(ammonium)⋯O(sulf-on-ate) and van der Waals inter-actions link the cations and anions together in a three-dimensional crystal structure, with zigzag rows of cations lying between layers of anions.

Related literature

The title compound was investigated as part of our search for simple ferroelectric compounds. For general background to ferroelectric metal-organic frameworks, see: Ye et al. (2006 ▶); Zhang et al. (2008 ▶, 2009 ▶, 2010 ▶); Fu et al. (2009 ▶). For a related structure, see: Wang & Yang (2011 ▶).

Experimental

Crystal data

2C3H10N+·C10H6O6S2 2−

M = 406.51

Monoclinic,

a = 8.3428 (17) Å

b = 10.502 (2) Å

c = 11.742 (2) Å

β = 105.81 (3)°

V = 989.8 (3) 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

10031 measured reflections

2265 independent reflections

2016 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.10

2265 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.36 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/S1600536811052718/bh2404sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052718/bh2404Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052718/bh2404Isup3.cml

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

2C3H10N+·C10H6O6S22−	F(000) = 432
Mr = 406.51	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3450 reflections
a = 8.3428 (17) Å	θ = 6.2–55.3°
b = 10.502 (2) Å	µ = 0.30 mm−1
c = 11.742 (2) Å	T = 293 K
β = 105.81 (3)°	Block, colourless
V = 989.8 (3) Å3	0.3 × 0.3 × 0.2 mm
Z = 2

Rigaku Mercury CCD diffractometer	2265 independent reflections
Radiation source: fine-focus sealed tube	2016 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −10→10
Tmin = 0.489, Tmax = 1.000	k = −13→13
10031 measured reflections	l = −15→15

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.3652P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2265 reflections	Δρmax = 0.28 e Å−3
119 parameters	Δρmin = −0.36 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.055 (4)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.7732 (3)	0.1761 (3)	0.4624 (2)	0.0783 (8)
H1B	0.7949	0.2389	0.4090	0.117*
H1C	0.6593	0.1826	0.4647	0.117*
H1D	0.7929	0.0927	0.4357	0.117*
C2	0.8549 (4)	0.1033 (3)	0.6651 (3)	0.0926 (10)
H2B	0.9280	0.1194	0.7423	0.139*
H2C	0.8760	0.0197	0.6395	0.139*
H2D	0.7413	0.1087	0.6683	0.139*
C3	0.8748 (4)	0.3266 (3)	0.6265 (3)	0.0824 (9)
H3B	0.9491	0.3339	0.7046	0.124*
H3C	0.7629	0.3436	0.6293	0.124*
H3D	0.9061	0.3868	0.5749	0.124*
C4	0.4055 (2)	0.39604 (16)	0.66437 (14)	0.0336 (4)
H4A	0.3567	0.3452	0.7105	0.040*
C5	0.37869 (18)	0.37009 (14)	0.54673 (13)	0.0279 (3)
C6	0.44909 (18)	0.44781 (14)	0.47321 (13)	0.0258 (3)
C7	0.4218 (2)	0.42584 (15)	0.35041 (14)	0.0315 (4)
H7A	0.3535	0.3589	0.3146	0.038*
C8	0.4940 (2)	0.50113 (16)	0.28418 (14)	0.0353 (4)
H8A	0.4764	0.4842	0.2040	0.042*
N1	0.88425 (18)	0.19790 (16)	0.58184 (15)	0.0444 (4)
H1E	0.9904	0.1864	0.5772	0.053*
O1	0.3624 (2)	0.15499 (14)	0.43979 (16)	0.0635 (5)
O2	0.21016 (15)	0.17580 (12)	0.58538 (12)	0.0406 (3)
O3	0.11286 (19)	0.28226 (17)	0.39993 (14)	0.0646 (5)
S1	0.25686 (5)	0.23499 (4)	0.48711 (4)	0.03500 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0441 (12)	0.127 (3)	0.0569 (15)	−0.0063 (14)	0.0017 (11)	−0.0125 (16)
C2	0.112 (2)	0.086 (2)	0.0729 (18)	−0.0519 (19)	0.0134 (17)	0.0023 (15)
C3	0.0762 (18)	0.0563 (15)	0.104 (2)	0.0190 (13)	0.0066 (16)	−0.0161 (14)
C4	0.0363 (8)	0.0363 (8)	0.0301 (8)	−0.0014 (7)	0.0123 (7)	0.0050 (6)
C5	0.0247 (7)	0.0274 (7)	0.0310 (8)	0.0002 (6)	0.0068 (6)	0.0011 (6)
C6	0.0256 (7)	0.0249 (7)	0.0265 (7)	0.0029 (6)	0.0064 (6)	0.0005 (6)
C7	0.0347 (8)	0.0298 (8)	0.0285 (8)	−0.0014 (6)	0.0061 (6)	−0.0041 (6)
C8	0.0423 (9)	0.0385 (9)	0.0254 (7)	−0.0014 (7)	0.0100 (7)	−0.0011 (6)
N1	0.0267 (7)	0.0521 (10)	0.0534 (10)	−0.0035 (6)	0.0092 (7)	−0.0075 (8)
O1	0.0751 (11)	0.0409 (8)	0.0925 (12)	−0.0193 (7)	0.0537 (10)	−0.0242 (8)
O2	0.0332 (6)	0.0420 (7)	0.0471 (7)	−0.0069 (5)	0.0118 (5)	0.0085 (5)
O3	0.0455 (8)	0.0811 (11)	0.0533 (9)	−0.0226 (8)	−0.0101 (7)	0.0189 (8)
S1	0.0322 (2)	0.0350 (3)	0.0379 (3)	−0.00957 (16)	0.00984 (17)	−0.00121 (16)

C1—N1	1.473 (3)	C4—H4A	0.9300
C1—H1B	0.9600	C5—C6	1.426 (2)
C1—H1C	0.9600	C5—S1	1.7744 (16)
C1—H1D	0.9600	C6—C7	1.416 (2)
C2—N1	1.460 (3)	C6—C6i	1.424 (3)
C2—H2B	0.9600	C7—C8	1.359 (2)
C2—H2C	0.9600	C7—H7A	0.9300
C2—H2D	0.9600	C8—C4i	1.400 (2)
C3—N1	1.459 (3)	C8—H8A	0.9300
C3—H3B	0.9600	N1—H1E	0.9100
C3—H3C	0.9600	O1—S1	1.4338 (15)
C3—H3D	0.9600	O2—S1	1.4541 (13)
C4—C5	1.365 (2)	O3—S1	1.4379 (16)
C4—C8i	1.400 (2)
N1—C1—H1B	109.5	C6—C5—S1	120.33 (11)
N1—C1—H1C	109.5	C7—C6—C6i	119.11 (17)
H1B—C1—H1C	109.5	C7—C6—C5	123.01 (14)
N1—C1—H1D	109.5	C6i—C6—C5	117.88 (16)
H1B—C1—H1D	109.5	C8—C7—C6	120.95 (15)
H1C—C1—H1D	109.5	C8—C7—H7A	119.5
N1—C2—H2B	109.5	C6—C7—H7A	119.5
N1—C2—H2C	109.5	C7—C8—C4i	120.58 (15)
H2B—C2—H2C	109.5	C7—C8—H8A	119.7
N1—C2—H2D	109.5	C4i—C8—H8A	119.7
H2B—C2—H2D	109.5	C3—N1—C2	110.7 (2)
H2C—C2—H2D	109.5	C3—N1—C1	113.8 (2)
N1—C3—H3B	109.5	C2—N1—C1	110.8 (2)
N1—C3—H3C	109.5	C3—N1—H1E	107.0
H3B—C3—H3C	109.5	C2—N1—H1E	107.0
N1—C3—H3D	109.5	C1—N1—H1E	107.0
H3B—C3—H3D	109.5	O1—S1—O3	114.11 (11)
H3C—C3—H3D	109.5	O1—S1—O2	112.49 (9)
C5—C4—C8i	120.29 (15)	O3—S1—O2	111.10 (8)
C5—C4—H4A	119.9	O1—S1—C5	105.98 (8)
C8i—C4—H4A	119.9	O3—S1—C5	106.41 (9)
C4—C5—C6	121.16 (14)	O2—S1—C5	106.10 (8)
C4—C5—S1	118.50 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1E···O2ii	0.91	1.81	2.718 (2)	173.
C1—H1C···O1	0.96	2.43	3.372 (3)	166
C2—H2B···O3iii	0.96	2.31	3.232 (4)	162
N1—H1E···S1ii	0.91	2.76	3.5967 (18)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1E⋯O2i	0.91	1.81	2.718 (2)	173
C1—H1C⋯O1	0.96	2.43	3.372 (3)	166
C2—H2B⋯O3ii	0.96	2.31	3.232 (4)	162

Symmetry codes: (i) ; (ii) .