Dimethyl-ammonium guanidinium naphthalene-1,5-disulfonate.

The asymmetric unit of the title salt, CH(6)N(3) (+)·C(2)H(8)N(+)·C(10)H(6)O(6)S(2) (2-), consists of one dimethyl-ammonium cation, one guanidinium cation, and two half naphthalene-1,5-disulfonate anions, which lie on inversion centers. N-H⋯O hydrogen bonds link the cations and anions into layers parallel to the ab plane. The layers have a sandwich-like structure, with the sulfonate groups and cations forming outer slices and the naphthalene ring systems inside.

Related literature

For nanoporous materials with two-dimensional hydrogen-bonded networks, see: Russell et al. (1997 ▶). For recent studies of organic and organic–inorganic salts with ferroelectric properties, see: Fu et al. (2009 ▶); Wu et al. (2011 ▶). For general background to structure phase transitions in closely related compounds, see: Ye et al. (2009 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

CH6N3 +·C2H8N+·C10H6O6S2 2−

M = 392.45

Triclinic,

a = 8.7782 (18) Å

b = 9.0316 (18) Å

c = 11.923 (2) Å

α = 87.10 (3)°

β = 74.74 (3)°

γ = 88.77 (3)°

V = 910.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.936, T max = 0.937

9502 measured reflections

4168 independent reflections

3097 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.121

S = 1.04

4168 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011099/yk2047sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011099/yk2047Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011099/yk2047Isup3.cml

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

CH6N3+·C2H8N+·C10H6O6S22−	Z = 2
Mr = 392.45	F(000) = 412
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7782 (18) Å	Cell parameters from 3638 reflections
b = 9.0316 (18) Å	θ = 3.0–27.5°
c = 11.923 (2) Å	µ = 0.33 mm−1
α = 87.10 (3)°	T = 293 K
β = 74.74 (3)°	Block, colourless
γ = 88.77 (3)°	0.20 × 0.20 × 0.20 mm
V = 910.7 (3) Å3

Rigaku SCXmini diffractometer	4168 independent reflections
Radiation source: fine-focus sealed tube	3097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −11→11
Tmin = 0.936, Tmax = 0.937	k = −11→11
9502 measured reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.289P] where P = (Fo2 + 2Fc2)/3
4168 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
S1	0.56454 (6)	0.60040 (6)	0.20852 (5)	0.04580 (17)
O1	0.72470 (18)	0.64764 (18)	0.19535 (15)	0.0537 (4)
O2	0.47542 (19)	0.71224 (18)	0.15867 (15)	0.0554 (4)
O3	0.5537 (2)	0.45431 (18)	0.16728 (16)	0.0605 (5)
C4	0.4733 (2)	0.5921 (2)	0.3610 (2)	0.0444 (5)
C5	0.3440 (3)	0.6794 (3)	0.4035 (2)	0.0574 (6)
H5	0.3017	0.7376	0.3523	0.069*
C6	0.2749 (3)	0.6819 (3)	0.5227 (3)	0.0650 (7)
H6	0.1878	0.7430	0.5500	0.078*
C7	0.3320 (3)	0.5973 (3)	0.5998 (2)	0.0523 (6)
H7	0.2843	0.6018	0.6791	0.063*
C8	0.4640 (2)	0.5017 (2)	0.5607 (2)	0.0427 (5)
C3	0.1383 (3)	0.4844 (2)	0.12679 (19)	0.0427 (5)
C1	0.6168 (4)	0.1027 (3)	0.0828 (3)	0.0689 (7)
H1A	0.5056	0.1163	0.0916	0.103*
H1B	0.6669	0.0753	0.0049	0.103*
H1C	0.6613	0.1934	0.0978	0.103*
C2	0.5666 (4)	0.0162 (4)	0.2865 (3)	0.0827 (9)
H2A	0.6138	0.1018	0.3077	0.124*
H2B	0.5807	−0.0678	0.3355	0.124*
H2C	0.4559	0.0344	0.2961	0.124*
N1	−0.0065 (2)	0.4450 (2)	0.1321 (2)	0.0606 (6)
H1D	−0.0779	0.5115	0.1317	0.073*
H1E	−0.0300	0.3526	0.1361	0.073*
N2	0.1747 (3)	0.6261 (2)	0.12075 (19)	0.0590 (5)
H2D	0.1034	0.6928	0.1203	0.071*
H2E	0.2697	0.6517	0.1173	0.071*
N3	0.2482 (2)	0.3819 (2)	0.12657 (18)	0.0556 (5)
H3A	0.2247	0.2896	0.1299	0.067*
H3B	0.3432	0.4077	0.1231	0.067*
N4	0.6420 (3)	−0.0140 (2)	0.1648 (2)	0.0598 (6)
H4A	0.7465	−0.0261	0.1558	0.072*
H4B	0.6042	−0.0995	0.1478	0.072*
C9	−0.0137 (2)	−0.0556 (2)	0.3530 (2)	0.0429 (5)
C10	−0.0994 (3)	−0.1839 (2)	0.3832 (2)	0.0513 (6)
H10	−0.1247	−0.2368	0.3256	0.062*
C11	−0.1487 (3)	−0.2353 (3)	0.4988 (2)	0.0553 (6)
H11	−0.2053	−0.3231	0.5174	0.066*
C12	−0.1155 (3)	−0.1596 (2)	0.5852 (2)	0.0471 (5)
H12	−0.1513	−0.1950	0.6622	0.057*
C13	−0.0266 (2)	−0.0268 (2)	0.55895 (19)	0.0400 (5)
S2	0.03040 (7)	0.01286 (6)	0.20605 (5)	0.04819 (17)
O4	0.1966 (2)	0.0447 (2)	0.16779 (16)	0.0668 (5)
O5	−0.0671 (2)	0.14568 (17)	0.20878 (16)	0.0590 (5)
O6	−0.0188 (2)	−0.10150 (18)	0.14233 (15)	0.0602 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0427 (3)	0.0350 (3)	0.0622 (4)	−0.0011 (2)	−0.0178 (3)	−0.0047 (2)
O1	0.0424 (9)	0.0513 (10)	0.0678 (11)	−0.0067 (7)	−0.0152 (8)	−0.0002 (8)
O2	0.0584 (10)	0.0448 (9)	0.0686 (11)	0.0028 (7)	−0.0273 (9)	0.0006 (8)
O3	0.0678 (11)	0.0400 (9)	0.0772 (12)	−0.0006 (8)	−0.0229 (9)	−0.0146 (8)
C4	0.0360 (11)	0.0324 (11)	0.0651 (15)	0.0022 (8)	−0.0140 (10)	−0.0035 (10)
C5	0.0471 (13)	0.0504 (14)	0.0751 (18)	0.0144 (11)	−0.0185 (12)	0.0007 (12)
C6	0.0512 (14)	0.0605 (16)	0.0755 (19)	0.0291 (12)	−0.0060 (13)	−0.0005 (13)
C7	0.0422 (12)	0.0445 (13)	0.0643 (16)	0.0123 (10)	−0.0045 (11)	−0.0032 (11)
C8	0.0332 (10)	0.0270 (10)	0.0672 (14)	0.0005 (8)	−0.0113 (9)	−0.0049 (9)
C3	0.0430 (12)	0.0413 (12)	0.0410 (12)	−0.0017 (9)	−0.0073 (9)	0.0038 (9)
C1	0.083 (2)	0.0507 (16)	0.0703 (19)	0.0003 (14)	−0.0156 (15)	−0.0022 (13)
C2	0.091 (2)	0.087 (2)	0.069 (2)	−0.0184 (18)	−0.0177 (17)	−0.0047 (16)
N1	0.0445 (11)	0.0447 (11)	0.0905 (16)	−0.0045 (9)	−0.0166 (11)	0.0133 (11)
N2	0.0546 (12)	0.0397 (11)	0.0831 (16)	−0.0032 (9)	−0.0198 (11)	0.0034 (10)
N3	0.0431 (11)	0.0402 (11)	0.0812 (15)	−0.0005 (8)	−0.0131 (10)	0.0006 (10)
N4	0.0527 (12)	0.0479 (12)	0.0803 (16)	0.0023 (9)	−0.0204 (11)	−0.0036 (10)
C9	0.0386 (11)	0.0312 (10)	0.0617 (14)	0.0016 (8)	−0.0181 (10)	−0.0046 (9)
C10	0.0539 (13)	0.0364 (12)	0.0693 (17)	−0.0070 (10)	−0.0249 (12)	−0.0084 (11)
C11	0.0559 (14)	0.0379 (12)	0.0763 (18)	−0.0165 (10)	−0.0238 (13)	−0.0006 (11)
C12	0.0428 (12)	0.0356 (11)	0.0636 (15)	−0.0065 (9)	−0.0151 (10)	−0.0003 (10)
C13	0.0296 (10)	0.0284 (10)	0.0645 (14)	0.0024 (8)	−0.0162 (9)	−0.0051 (9)
S2	0.0479 (3)	0.0357 (3)	0.0614 (4)	−0.0034 (2)	−0.0142 (3)	−0.0054 (2)
O4	0.0489 (10)	0.0736 (13)	0.0720 (12)	−0.0070 (9)	−0.0026 (8)	−0.0166 (10)
O5	0.0647 (11)	0.0373 (9)	0.0733 (12)	0.0020 (8)	−0.0168 (9)	0.0048 (8)
O6	0.0807 (12)	0.0417 (9)	0.0647 (11)	−0.0087 (8)	−0.0296 (9)	−0.0050 (8)

S1—O1	1.4442 (16)	C2—H2C	0.9600
S1—O3	1.4448 (17)	N1—H1D	0.8600
S1—O2	1.4614 (17)	N1—H1E	0.8600
S1—C4	1.782 (3)	N2—H2D	0.8600
C4—C5	1.366 (3)	N2—H2E	0.8600
C4—C8i	1.436 (3)	N3—H3A	0.8600
C5—C6	1.392 (4)	N3—H3B	0.8600
C5—H5	0.9300	N4—H4A	0.9000
C6—C7	1.354 (4)	N4—H4B	0.9000
C6—H6	0.9300	C9—C10	1.375 (3)
C7—C8	1.421 (3)	C9—C13ii	1.437 (3)
C7—H7	0.9300	C9—S2	1.774 (2)
C8—C8i	1.421 (5)	C10—C11	1.391 (3)
C8—C4i	1.436 (3)	C10—H10	0.9300
C3—N1	1.312 (3)	C11—C12	1.362 (3)
C3—N2	1.320 (3)	C11—H11	0.9300
C3—N3	1.322 (3)	C12—C13	1.421 (3)
C1—N4	1.454 (3)	C12—H12	0.9300
C1—H1A	0.9600	C13—C13ii	1.422 (4)
C1—H1B	0.9600	C13—C9ii	1.437 (3)
C1—H1C	0.9600	S2—O4	1.4404 (18)
C2—N4	1.465 (4)	S2—O6	1.4496 (17)
C2—H2A	0.9600	S2—O5	1.4552 (17)
C2—H2B	0.9600
O1—S1—O3	113.70 (11)	C3—N1—H1D	120.0
O1—S1—O2	111.13 (10)	C3—N1—H1E	120.0
O3—S1—O2	112.70 (11)	H1D—N1—H1E	120.0
O1—S1—C4	105.95 (10)	C3—N2—H2D	120.0
O3—S1—C4	107.12 (11)	C3—N2—H2E	120.0
O2—S1—C4	105.59 (10)	H2D—N2—H2E	120.0
C5—C4—C8i	120.0 (2)	C3—N3—H3A	120.0
C5—C4—S1	118.99 (19)	C3—N3—H3B	120.0
C8i—C4—S1	121.01 (16)	H3A—N3—H3B	120.0
C4—C5—C6	120.5 (2)	C1—N4—C2	113.6 (2)
C4—C5—H5	119.7	C1—N4—H4A	108.9
C6—C5—H5	119.7	C2—N4—H4A	108.9
C7—C6—C5	121.4 (2)	C1—N4—H4B	108.9
C7—C6—H6	119.3	C2—N4—H4B	108.9
C5—C6—H6	119.3	H4A—N4—H4B	107.7
C6—C7—C8	120.6 (2)	C10—C9—C13ii	120.2 (2)
C6—C7—H7	119.7	C10—C9—S2	118.36 (18)
C8—C7—H7	119.7	C13ii—C9—S2	121.21 (16)
C8i—C8—C7	118.6 (3)	C9—C10—C11	120.6 (2)
C8i—C8—C4i	118.8 (2)	C9—C10—H10	119.7
C7—C8—C4i	122.6 (2)	C11—C10—H10	119.7
N1—C3—N2	120.1 (2)	C12—C11—C10	121.2 (2)
N1—C3—N3	119.9 (2)	C12—C11—H11	119.4
N2—C3—N3	119.9 (2)	C10—C11—H11	119.4
N4—C1—H1A	109.5	C11—C12—C13	120.5 (2)
N4—C1—H1B	109.5	C11—C12—H12	119.7
H1A—C1—H1B	109.5	C13—C12—H12	119.7
N4—C1—H1C	109.5	C12—C13—C13ii	119.2 (2)
H1A—C1—H1C	109.5	C12—C13—C9ii	122.6 (2)
H1B—C1—H1C	109.5	C13ii—C13—C9ii	118.3 (2)
N4—C2—H2A	109.5	O4—S2—O6	113.80 (11)
N4—C2—H2B	109.5	O4—S2—O5	112.38 (11)
H2A—C2—H2B	109.5	O6—S2—O5	111.31 (11)
N4—C2—H2C	109.5	O4—S2—C9	108.35 (11)
H2A—C2—H2C	109.5	O6—S2—C9	105.83 (10)
H2B—C2—H2C	109.5	O5—S2—C9	104.46 (10)
O1—S1—C4—C5	119.8 (2)	C13ii—C9—C10—C11	0.3 (3)
O3—S1—C4—C5	−118.5 (2)	S2—C9—C10—C11	−174.47 (18)
O2—S1—C4—C5	1.8 (2)	C9—C10—C11—C12	0.9 (4)
O1—S1—C4—C8i	−58.72 (19)	C10—C11—C12—C13	−1.2 (4)
O3—S1—C4—C8i	62.98 (19)	C11—C12—C13—C13ii	0.4 (4)
O2—S1—C4—C8i	−176.68 (16)	C11—C12—C13—C9ii	−178.9 (2)
C8i—C4—C5—C6	2.1 (4)	C10—C9—S2—O4	−130.74 (19)
S1—C4—C5—C6	−176.5 (2)	C13ii—C9—S2—O4	54.60 (19)
C4—C5—C6—C7	−0.8 (4)	C10—C9—S2—O6	−8.3 (2)
C5—C6—C7—C8	−0.7 (4)	C13ii—C9—S2—O6	177.01 (16)
C6—C7—C8—C8i	0.8 (4)	C10—C9—S2—O5	109.27 (19)
C6—C7—C8—C4i	−178.7 (2)	C13ii—C9—S2—O5	−65.39 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1iii	0.86	2.10	2.916 (3)	159
N1—H1E···O5	0.86	2.02	2.825 (3)	157
N2—H2D···O6iv	0.86	2.12	2.942 (3)	160
N2—H2E···O2	0.86	2.08	2.921 (3)	164
N3—H3A···O4	0.86	2.24	3.084 (3)	167
N3—H3B···O3	0.86	2.11	2.940 (3)	163
N4—H4A···O6v	0.90	2.12	3.011 (3)	168
N4—H4A···O5v	0.90	2.50	3.133 (3)	128
N4—H4B···O1vi	0.90	2.60	3.152 (3)	121
N4—H4B···O2vi	0.90	2.04	2.914 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O1i	0.86	2.10	2.916 (3)	159
N1—H1E⋯O5	0.86	2.02	2.825 (3)	157
N2—H2D⋯O6ii	0.86	2.12	2.942 (3)	160
N2—H2E⋯O2	0.86	2.08	2.921 (3)	164
N3—H3A⋯O4	0.86	2.24	3.084 (3)	167
N3—H3B⋯O3	0.86	2.11	2.940 (3)	163
N4—H4A⋯O6iii	0.90	2.12	3.011 (3)	168
N4—H4A⋯O5iii	0.90	2.50	3.133 (3)	128
N4—H4B⋯O1iv	0.90	2.60	3.152 (3)	121
N4—H4B⋯O2iv	0.90	2.04	2.914 (3)	163

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