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

In the title compound, 2C(6)H(16)N(+)·C(10)H(6)O(6)S(2) (2-), the cations and anions are associated via N-H⋯O and C-H⋯O hydrogen-bonding inter-actions.

Related literature

For general background on ferroelectric metal–organic frameworks, see: Fu et al. (2009 ▶); Wu et al. (2011 ▶); Ye et al. (2006 ▶); Zhang et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

2C6H16N+·C10H6O6S2 2−

M = 490.66

Triclinic,

a = 7.9518 (16) Å

b = 9.1215 (18) Å

c = 9.4319 (19) Å

α = 74.33 (3)°

β = 88.60 (3)°

γ = 74.74 (3)°

V = 634.7 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.25 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

6562 measured reflections

2904 independent reflections

2621 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.129

S = 1.12

2904 reflections

150 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.45 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/S1600536811043492/mw2025sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043492/mw2025Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043492/mw2025Isup3.cml

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

2C6H16N+·C10H6O6S22−	Z = 1
Mr = 490.66	F(000) = 264
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9518 (16) Å	Cell parameters from 3450 reflections
b = 9.1215 (18) Å	θ = 3.1–27.6°
c = 9.4319 (19) Å	µ = 0.25 mm−1
α = 74.33 (3)°	T = 293 K
β = 88.60 (3)°	Block, colorless
γ = 74.74 (3)°	0.3 × 0.3 × 0.2 mm
V = 634.7 (2) Å3

Rigaku Mercury CCD diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	2621 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −10→10
Tmin = 0.489, Tmax = 1.000	k = −11→11
6562 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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0558P)2 + 0.2055P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2904 reflections	Δρmax = 0.50 e Å−3
150 parameters	Δρmin = −0.45 e Å−3
0 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: 0.85 (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	−0.0351 (2)	0.2895 (2)	0.7281 (2)	0.0369 (4)
H1B	−0.0197	0.2081	0.8148	0.044*
C2	0.1044 (2)	0.34189 (18)	0.66995 (17)	0.0283 (3)
C3	0.08495 (18)	0.46559 (17)	0.53574 (17)	0.0259 (3)
C4	0.2268 (2)	0.5223 (2)	0.47013 (19)	0.0337 (4)
H4A	0.3383	0.4773	0.5148	0.040*
C5	0.2021 (2)	0.6413 (2)	0.3430 (2)	0.0406 (4)
H5A	0.2965	0.6774	0.3026	0.049*
C6	0.1682 (3)	0.0620 (3)	0.2747 (3)	0.0628 (7)
H6A	0.2490	−0.0343	0.3287	0.094*
H6B	0.1388	0.0527	0.1800	0.094*
H6C	0.0643	0.0818	0.3284	0.094*
C7	0.2506 (2)	0.1971 (2)	0.2543 (2)	0.0429 (4)
H7A	0.2742	0.2097	0.3512	0.052*
C8	0.1320 (3)	0.3506 (3)	0.1613 (3)	0.0607 (6)
H8A	0.1903	0.4329	0.1461	0.091*
H8B	0.0266	0.3784	0.2112	0.091*
H8C	0.1040	0.3377	0.0677	0.091*
C9	0.6308 (4)	0.2023 (4)	0.3419 (3)	0.0714 (8)
H9A	0.5432	0.2048	0.4137	0.107*
H9B	0.7008	0.2709	0.3505	0.107*
H9C	0.7036	0.0964	0.3585	0.107*
C10	0.5439 (3)	0.2570 (2)	0.1895 (2)	0.0437 (5)
H10A	0.4767	0.3676	0.1709	0.052*
C11	0.6760 (3)	0.2441 (4)	0.0729 (3)	0.0661 (7)
H11A	0.7547	0.3062	0.0787	0.099*
H11B	0.6168	0.2822	−0.0227	0.099*
H11C	0.7404	0.1356	0.0886	0.099*
N1	0.42071 (17)	0.15825 (17)	0.18060 (16)	0.0335 (3)
H1C	0.3967	0.1694	0.0849	0.040*
H1D	0.4761	0.0560	0.2216	0.040*
O1	0.28340 (19)	0.14639 (18)	0.90458 (15)	0.0519 (4)
O2	0.3674 (2)	0.38559 (19)	0.79367 (18)	0.0585 (4)
O3	0.42442 (18)	0.17516 (17)	0.67405 (16)	0.0517 (4)
S1	0.31154 (5)	0.25661 (5)	0.76799 (5)	0.0357 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0390 (9)	0.0366 (9)	0.0327 (9)	−0.0133 (7)	0.0020 (7)	−0.0025 (7)
C2	0.0264 (7)	0.0285 (7)	0.0287 (8)	−0.0033 (6)	−0.0008 (6)	−0.0096 (6)
C3	0.0231 (7)	0.0279 (7)	0.0276 (7)	−0.0059 (6)	−0.0001 (6)	−0.0101 (6)
C4	0.0227 (7)	0.0399 (9)	0.0384 (9)	−0.0087 (6)	−0.0004 (6)	−0.0101 (7)
C5	0.0328 (9)	0.0468 (10)	0.0426 (10)	−0.0186 (8)	0.0049 (7)	−0.0054 (8)
C6	0.0394 (11)	0.0591 (14)	0.0805 (17)	−0.0143 (10)	0.0068 (11)	−0.0030 (12)
C7	0.0350 (9)	0.0497 (11)	0.0442 (10)	−0.0058 (8)	0.0055 (7)	−0.0187 (8)
C8	0.0441 (12)	0.0442 (11)	0.0883 (18)	0.0052 (9)	0.0023 (11)	−0.0255 (12)
C9	0.0689 (16)	0.118 (2)	0.0499 (13)	−0.0474 (16)	0.0010 (11)	−0.0383 (14)
C10	0.0414 (10)	0.0422 (10)	0.0495 (11)	−0.0152 (8)	−0.0024 (8)	−0.0114 (8)
C11	0.0519 (13)	0.105 (2)	0.0431 (12)	−0.0390 (13)	0.0018 (10)	−0.0054 (12)
N1	0.0291 (7)	0.0354 (7)	0.0345 (7)	−0.0038 (6)	−0.0022 (5)	−0.0115 (6)
O1	0.0527 (9)	0.0584 (9)	0.0318 (7)	−0.0073 (7)	−0.0081 (6)	0.0023 (6)
O2	0.0545 (9)	0.0595 (9)	0.0644 (10)	−0.0164 (7)	−0.0242 (7)	−0.0182 (8)
O3	0.0412 (8)	0.0515 (8)	0.0456 (8)	0.0119 (6)	0.0027 (6)	−0.0090 (6)
S1	0.0306 (3)	0.0390 (3)	0.0310 (3)	−0.00070 (17)	−0.00660 (16)	−0.00666 (18)

C1—C2	1.366 (2)	C8—H8A	0.9600
C1—C5i	1.409 (3)	C8—H8B	0.9600
C1—H1B	0.9300	C8—H8C	0.9600
C2—C3	1.430 (2)	C9—C10	1.507 (3)
C2—S1	1.7844 (17)	C9—H9A	0.9600
C3—C4	1.422 (2)	C9—H9B	0.9600
C3—C3i	1.430 (3)	C9—H9C	0.9600
C4—C5	1.360 (3)	C10—C11	1.508 (3)
C4—H4A	0.9300	C10—N1	1.513 (2)
C5—C1i	1.409 (3)	C10—H10A	0.9800
C5—H5A	0.9300	C11—H11A	0.9600
C6—C7	1.508 (3)	C11—H11B	0.9600
C6—H6A	0.9600	C11—H11C	0.9600
C6—H6B	0.9600	N1—H1C	0.9000
C6—H6C	0.9600	N1—H1D	0.9000
C7—N1	1.508 (2)	O1—S1	1.4578 (15)
C7—C8	1.517 (3)	O2—S1	1.4401 (16)
C7—H7A	0.9800	O3—S1	1.4521 (15)
C2—C1—C5i	120.17 (16)	H8B—C8—H8C	109.5
C2—C1—H1B	119.9	C10—C9—H9A	109.5
C5i—C1—H1B	119.9	C10—C9—H9B	109.5
C1—C2—C3	121.06 (15)	H9A—C9—H9B	109.5
C1—C2—S1	118.57 (13)	C10—C9—H9C	109.5
C3—C2—S1	120.34 (12)	H9A—C9—H9C	109.5
C4—C3—C3i	118.72 (18)	H9B—C9—H9C	109.5
C4—C3—C2	123.01 (14)	C9—C10—C11	111.56 (19)
C3i—C3—C2	118.28 (17)	C9—C10—N1	109.39 (17)
C5—C4—C3	121.05 (15)	C11—C10—N1	109.33 (17)
C5—C4—H4A	119.5	C9—C10—H10A	108.8
C3—C4—H4A	119.5	C11—C10—H10A	108.8
C4—C5—C1i	120.72 (16)	N1—C10—H10A	108.8
C4—C5—H5A	119.6	C10—C11—H11A	109.5
C1i—C5—H5A	119.6	C10—C11—H11B	109.5
C7—C6—H6A	109.5	H11A—C11—H11B	109.5
C7—C6—H6B	109.5	C10—C11—H11C	109.5
H6A—C6—H6B	109.5	H11A—C11—H11C	109.5
C7—C6—H6C	109.5	H11B—C11—H11C	109.5
H6A—C6—H6C	109.5	C7—N1—C10	115.64 (14)
H6B—C6—H6C	109.5	C7—N1—H1C	108.4
N1—C7—C6	108.75 (16)	C10—N1—H1C	108.4
N1—C7—C8	109.60 (17)	C7—N1—H1D	108.4
C6—C7—C8	111.47 (19)	C10—N1—H1D	108.4
N1—C7—H7A	109.0	H1C—N1—H1D	107.4
C6—C7—H7A	109.0	O2—S1—O3	113.49 (10)
C8—C7—H7A	109.0	O2—S1—O1	112.42 (10)
C7—C8—H8A	109.5	O3—S1—O1	111.45 (9)
C7—C8—H8B	109.5	O2—S1—C2	106.31 (8)
H8A—C8—H8B	109.5	O3—S1—C2	106.05 (8)
C7—C8—H8C	109.5	O1—S1—C2	106.53 (8)
H8A—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1ii	0.90	2.03	2.887 (2)	159
N1—H1D···O3iii	0.90	2.02	2.916 (2)	174
C9—H9A···O3	0.96	2.58	3.480 (3)	156
C6—H6A···O3iii	0.96	2.58	3.351 (3)	138
C11—H11C···O1iii	0.96	2.61	3.439 (4)	144
C11—H11B···O2ii	0.96	2.47	3.382 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1i	0.90	2.03	2.887 (2)	159
N1—H1D⋯O3ii	0.90	2.02	2.916 (2)	174
C9—H9A⋯O3	0.96	2.58	3.480 (3)	156
C6—H6A⋯O3ii	0.96	2.58	3.351 (3)	138
C11—H11C⋯O1ii	0.96	2.61	3.439 (4)	144
C11—H11B⋯O2i	0.96	2.47	3.382 (3)	158

Symmetry codes: (i) ; (ii) .