Dimethyl­ammonium guanidinium naphthalene-1,5-disulfonate

Wei, B.

doi:10.1107/S1600536812011099

organic compounds

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Volume 68| Part 4| April 2012| Page o1123

doi:10.1107/S1600536812011099

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Dimethylammonium guanidinium naphthalene-1,5-disulfonate

Bin Wei ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: seuwei@126.com

(Received 28 February 2012; accepted 14 March 2012; online 21 March 2012)

The asymmetric unit of the title salt, CH₆N₃⁺·C₂H₈N⁺·C₁₀H₆O₆S₂²⁻, consists of one dimethylammonium 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⁺·C₁₀H₆O₆S₂²⁻
M_r = 392.45
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.04
4168 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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⋯O1^iv	0.90	2.60	3.152 (3)	121
N4—H4B⋯O2^iv	0.90	2.04	2.914 (3)	163
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x, y-1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812011099/yk2047sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812011099/yk2047Isup3.cml

checkCIF report

Comment top

Recently a series of nanoporous materials has been reported, which have two-dimensional hydrogen-bond networks and adjustable porosity (Russell et al., 1997). Guanidinium ions and the sulfonate groups of arenedisulfonate ions can form rich variety of H-bonds. We prepared the title compound in attempts to find new hydrogen-bonded dielectric materials consisting of guanidinium and naphthalene-1,5-disulfonate ions. Unfortunately, the study of dielectric permeability of the title compound indicated that its dielectric constant is essentially temperature-independent below its melting point (388 — 390 K). Thus we have found that the title compound has no dielectric disuniform from 80 K to 405 K.

At room temperature (25°C), the asymmetric unit of the title compound consists of one dimethylammonium cation, one guanidinium cation, and two halves of naphthalene-1,5-disulfonate anions, which lie at inversion centers (Fig. 1). The N—H···O hydrogen bonds join cations and anions into layers parallel to the ab plane. Layers have sandwich-like structure: sulfonate groups and cations form outer slices and naphthalene bicycles are inside. (Fig. 2).

Related literature top

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 top

The 1,5-naphthalenedisulfonic acid (1.824 g 8 mmol) and guanidinium tetrafluoroborate (0.588 g 4 mmol) were combined in 30 ml aqueous solution, and methanol solution of dimethylamine (0.326 g 4 mmol) was added to the mixture. The solution was stirred for 30 min to complete the reaction, and good quality blocky single crystals were obtained by slow evaporation of the filtrate after two weeks (chemical yield is 62%).

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. Asymmetric unit of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the packing of the title compound. Dashed lines indicate hydrogen bonds.

Dimethylammonium guanidinium naphthalene-1,5-disulfonate top

Crystal data top

CH₆N₃⁺·C₂H₈N⁺·C₁₀H₆O₆S₂²⁻	Z = 2
M_r = 392.45	F(000) = 412
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0492P)² + 0.289P] where P = (F_o² + 2F_c²)/3
4168 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

CH₆N₃⁺·C₂H₈N⁺·C₁₀H₆O₆S₂²⁻	γ = 88.77 (3)°
M_r = 392.45	V = 910.7 (3) Å³
Triclinic, P1	Z = 2
a = 8.7782 (18) Å	Mo Kα radiation
b = 9.0316 (18) Å	µ = 0.33 mm⁻¹
c = 11.923 (2) Å	T = 293 K
α = 87.10 (3)°	0.20 × 0.20 × 0.20 mm
β = 74.74 (3)°

Data collection top

Rigaku SCXmini diffractometer	4168 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3097 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.937	R_int = 0.031
9502 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
4168 reflections	Δρ_min = −0.29 e Å⁻³
228 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

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···O6^iv	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···O6^v	0.90	2.12	3.011 (3)	168
N4—H4A···O5^v	0.90	2.50	3.133 (3)	128
N4—H4B···O1^vi	0.90	2.60	3.152 (3)	121
N4—H4B···O2^vi	0.90	2.04	2.914 (3)	163

Symmetry codes: (iii) x−1, y, z; (iv) x, y+1, z; (v) x+1, y, z; (vi) x, y−1, z.

Experimental details

Crystal data
Chemical formula	CH₆N₃⁺·C₂H₈N⁺·C₁₀H₆O₆S₂²⁻
M_r	392.45
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.7782 (18), 9.0316 (18), 11.923 (2)
α, β, γ (°)	87.10 (3), 74.74 (3), 88.77 (3)
V (Å³)	910.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.936, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	9502, 4168, 3097
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.04
No. of reflections	4168
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1ⁱ	0.86	2.10	2.916 (3)	158.8
N1—H1E···O5	0.86	2.02	2.825 (3)	156.5
N2—H2D···O6ⁱⁱ	0.86	2.12	2.942 (3)	160.4
N2—H2E···O2	0.86	2.08	2.921 (3)	164.1
N3—H3A···O4	0.86	2.24	3.084 (3)	167.0
N3—H3B···O3	0.86	2.11	2.940 (3)	163.1
N4—H4A···O6ⁱⁱⁱ	0.90	2.12	3.011 (3)	168.2
N4—H4A···O5ⁱⁱⁱ	0.90	2.50	3.133 (3)	128.0
N4—H4B···O1^iv	0.90	2.60	3.152 (3)	120.7
N4—H4B···O2^iv	0.90	2.04	2.914 (3)	162.7

Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x, y−1, z.

Acknowledgements

The author is grateful to the starter fund of Southeast University for the purchase of the diffractometer.

References

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