Benzene-1,2-di(aminium) naphthalene-1,5-disulfonate methanol monosolvate trihydrate.

In the title salt, C(6)H(10)N(2) (2+)·C(10)H(6)O(6)S(2) (2-)·CH(3)OH·3H(2)O, the cation lies on a mirror plane and the anion on a center of inversion. One lattice water mol-ecule is located on a mirror plane, another is equally disordered over two sites. The methanol solvent mol-ecule is disordered about a mirror plane. In the crystal, the cations, anions, water and methanol mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For other diammonium napthalene-1,5-disulfonates, see: Wei (2011 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C6H10N2 2+·C10H6O6S2 2−·CH4O·3H2O

M = 482.52

Monoclinic,

a = 8.1727 (15) Å

b = 13.681 (2) Å

c = 9.5173 (15) Å

β = 98.390 (5)°

V = 1052.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.926, T max = 0.943

10378 measured reflections

2503 independent reflections

1935 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.176

S = 1.13

2503 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.41 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018284/xu5520sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018284/xu5520Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018284/xu5520Isup3.cml

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

C6H10N22+·C10H6O6S22−·CH4O·3H2O	F(000) = 508
Mr = 482.52	Dx = 1.522 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 6427 reflections
a = 8.1727 (15) Å	θ = 3.1–27.5°
b = 13.681 (2) Å	µ = 0.31 mm−1
c = 9.5173 (15) Å	T = 293 K
β = 98.390 (5)°	Prism, colorless
V = 1052.8 (3) Å3	0.25 × 0.22 × 0.19 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	2503 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
ω scan	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.926, Tmax = 0.943	k = −16→17
10378 measured reflections	l = −12→12

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0909P)2 + 0.6772P] where P = (Fo2 + 2Fc2)/3
2503 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.71163 (7)	0.51770 (5)	0.72850 (6)	0.0322 (2)
O1	0.6469 (2)	0.61258 (14)	0.6776 (2)	0.0425 (5)
O2	0.6097 (2)	0.43755 (15)	0.6701 (2)	0.0443 (5)
O3	0.7450 (3)	0.51585 (15)	0.8836 (2)	0.0433 (5)
O1w	0.5509 (5)	0.7500	1.2108 (4)	0.0707 (10)
H1w	0.4934	0.6998	1.1902	0.106*
N1	0.4198 (5)	0.7500	0.7729 (4)	0.0509 (9)
H11	0.3788	0.7500	0.8535	0.076*
H12	0.4809	0.8025	0.7685	0.076*
N2	0.4862 (4)	0.7500	0.4847 (3)	0.0368 (7)
H21	0.4867	0.7500	0.3923	0.055*
H22	0.5374	0.6975	0.5221	0.055*
C1	0.9077 (3)	0.50513 (18)	0.6689 (3)	0.0300 (5)
C2	0.9198 (3)	0.50489 (17)	0.5204 (3)	0.0292 (5)
C3	0.7803 (3)	0.51357 (19)	0.4131 (3)	0.0338 (6)
H3	0.6752	0.5191	0.4388	0.041*
C4	0.7984 (3)	0.5140 (2)	0.2731 (3)	0.0387 (6)
H4A	0.7057	0.5207	0.2045	0.046*
C5	0.9552 (3)	0.5044 (2)	0.2309 (3)	0.0373 (6)
H5	0.9659	0.5044	0.1349	0.045*
C6	0.2850 (5)	0.7500	0.6545 (4)	0.0354 (8)
C7	0.1240 (5)	0.7500	0.6818 (5)	0.0453 (10)
H7	0.1025	0.7500	0.7751	0.054*
C8	−0.0050 (5)	0.7500	0.5712 (6)	0.0527 (11)
H8	−0.1133	0.7500	0.5904	0.063*
C9	0.0245 (6)	0.7500	0.4325 (5)	0.0499 (10)
H9	−0.0631	0.7500	0.3582	0.060*
C10	0.1866 (5)	0.7500	0.4045 (4)	0.0431 (9)
H10	0.2077	0.7500	0.3111	0.052*
C11	0.3153 (4)	0.7500	0.5139 (4)	0.0315 (7)
O4	0.7361 (8)	0.6961 (4)	1.0177 (6)	0.0782 (17)	0.50
H4	0.7426	0.6406	0.9812	0.117*	0.50
C12	0.8778 (11)	0.751 (2)	1.0006 (8)	0.090 (3)	0.5
H12A	0.8778	0.8110	1.0533	0.135*	0.50
H12B	0.8767	0.7658	0.9018	0.135*	0.50
H12C	0.9753	0.7143	1.0351	0.135*	0.50
O2w	0.4770 (6)	0.6054 (4)	0.9855 (5)	0.0635 (13)	0.50
H2w1	0.3897	0.6342	0.9987	0.095*	0.50
H2w2	0.4637	0.5451	0.9955	0.095*	0.50
O2w'	0.2979 (7)	0.6729 (4)	1.0117 (5)	0.0657 (13)	0.50
H2w3	0.3789	0.6375	1.0001	0.099*	0.50
H2w4	0.2196	0.6366	1.0271	0.099*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0272 (4)	0.0378 (4)	0.0335 (4)	0.0033 (2)	0.0108 (2)	0.0024 (2)
O1	0.0421 (11)	0.0428 (11)	0.0451 (10)	0.0138 (9)	0.0152 (8)	0.0056 (9)
O2	0.0313 (10)	0.0483 (12)	0.0553 (12)	−0.0061 (8)	0.0127 (8)	−0.0051 (10)
O3	0.0434 (11)	0.0557 (12)	0.0333 (10)	0.0051 (9)	0.0143 (8)	0.0054 (9)
O1w	0.086 (3)	0.083 (3)	0.0472 (18)	0.000	0.0224 (18)	0.000
N1	0.044 (2)	0.074 (3)	0.0366 (17)	0.000	0.0125 (15)	0.000
N2	0.0354 (17)	0.0422 (17)	0.0341 (16)	0.000	0.0096 (13)	0.000
C1	0.0241 (12)	0.0339 (12)	0.0335 (13)	0.0028 (9)	0.0096 (9)	0.0008 (10)
C2	0.0265 (13)	0.0297 (12)	0.0314 (12)	0.0016 (9)	0.0045 (9)	0.0021 (10)
C3	0.0219 (12)	0.0428 (14)	0.0367 (13)	0.0009 (10)	0.0050 (10)	0.0003 (11)
C4	0.0281 (13)	0.0520 (17)	0.0343 (14)	0.0034 (11)	−0.0007 (10)	0.0015 (11)
C5	0.0339 (14)	0.0480 (15)	0.0299 (12)	0.0026 (11)	0.0045 (10)	0.0024 (11)
C6	0.038 (2)	0.0342 (18)	0.0360 (18)	0.000	0.0101 (15)	0.000
C7	0.043 (2)	0.044 (2)	0.054 (2)	0.000	0.0200 (19)	0.000
C8	0.032 (2)	0.048 (2)	0.081 (3)	0.000	0.016 (2)	0.000
C9	0.038 (2)	0.045 (2)	0.064 (3)	0.000	−0.0007 (19)	0.000
C10	0.043 (2)	0.045 (2)	0.040 (2)	0.000	0.0021 (17)	0.000
C11	0.0317 (18)	0.0271 (16)	0.0372 (18)	0.000	0.0100 (14)	0.000
O4	0.098 (4)	0.069 (3)	0.079 (4)	−0.002 (3)	0.050 (3)	−0.012 (3)
C12	0.097 (6)	0.093 (6)	0.086 (5)	0.035 (14)	0.031 (4)	−0.009 (16)
O2w	0.067 (3)	0.060 (3)	0.066 (3)	0.004 (2)	0.020 (2)	0.002 (2)
O2w'	0.071 (3)	0.077 (3)	0.051 (3)	−0.010 (3)	0.015 (2)	0.011 (2)

S1—O2	1.439 (2)	C6—C7	1.377 (5)
S1—O1	1.4578 (19)	C6—C11	1.396 (5)
S1—O3	1.461 (2)	C7—C8	1.377 (7)
S1—C1	1.785 (2)	C7—H7	0.9300
O1w—H1w	0.8391	C8—C9	1.376 (7)
N1—C6	1.456 (5)	C8—H8	0.9300
N1—H11	0.8800	C9—C10	1.389 (6)
N1—H12	0.8800	C9—H9	0.9300
N2—C11	1.463 (4)	C10—C11	1.368 (5)
N2—H21	0.8800	C10—H10	0.9300
N2—H22	0.8800	O4—C12	1.41 (2)
C1—C5i	1.367 (4)	O4—H4	0.8400
C1—C2	1.430 (3)	C12—H12A	0.9600
C2—C3	1.420 (4)	C12—H12B	0.9600
C2—C2i	1.428 (5)	C12—H12C	0.9600
C3—C4	1.362 (4)	O2w—H2w1	0.8401
C3—H3	0.9300	O2w—H2w2	0.8400
C4—C5	1.404 (4)	O2w—H2w3	0.9423
C4—H4A	0.9300	O2w'—H2w1	0.9412
C5—C1i	1.367 (4)	O2w'—H2w3	0.8400
C5—H5	0.9300	O2w'—H2w4	0.8400
O2—S1—O1	112.86 (13)	C1i—C5—H5	120.1
O2—S1—O3	112.92 (12)	C4—C5—H5	120.1
O1—S1—O3	110.88 (12)	C7—C6—C11	119.2 (4)
O2—S1—C1	107.45 (12)	C7—C6—N1	119.3 (3)
O1—S1—C1	106.22 (12)	C11—C6—N1	121.5 (3)
O3—S1—C1	105.98 (12)	C8—C7—C6	120.1 (4)
C6—N1—H11	109.5	C8—C7—H7	119.9
C6—N1—H12	109.5	C6—C7—H7	119.9
H11—N1—H12	109.5	C9—C8—C7	120.8 (4)
C11—N2—H21	109.5	C9—C8—H8	119.6
C11—N2—H22	109.5	C7—C8—H8	119.6
H21—N2—H22	109.5	C8—C9—C10	119.3 (4)
C5i—C1—C2	121.4 (2)	C8—C9—H9	120.3
C5i—C1—S1	118.00 (19)	C10—C9—H9	120.3
C2—C1—S1	120.56 (19)	C11—C10—C9	120.2 (4)
C3—C2—C2i	119.0 (3)	C11—C10—H10	119.9
C3—C2—C1	123.1 (2)	C9—C10—H10	119.9
C2i—C2—C1	117.9 (3)	C10—C11—C6	120.4 (3)
C4—C3—C2	120.9 (2)	C10—C11—N2	120.3 (3)
C4—C3—H3	119.6	C6—C11—N2	119.3 (3)
C2—C3—H3	119.6	H2w1—O2w—H2w2	108.5
C3—C4—C5	120.9 (2)	H2w2—O2w—H2w3	108.3
C3—C4—H4A	119.5	H2w1—O2w'—H2w4	109.5
C5—C4—H4A	119.5	H2w3—O2w'—H2w4	108.5
C1i—C5—C4	119.9 (2)
O2—S1—C1—C5i	−120.4 (2)	C3—C4—C5—C1i	−0.3 (4)
O1—S1—C1—C5i	118.6 (2)	C11—C6—C7—C8	0.000 (2)
O3—S1—C1—C5i	0.6 (3)	N1—C6—C7—C8	180.000 (1)
O2—S1—C1—C2	59.5 (2)	C6—C7—C8—C9	0.000 (2)
O1—S1—C1—C2	−61.5 (2)	C7—C8—C9—C10	0.000 (2)
O3—S1—C1—C2	−179.51 (19)	C8—C9—C10—C11	0.000 (1)
C5i—C1—C2—C3	179.3 (3)	C9—C10—C11—C6	0.0
S1—C1—C2—C3	−0.5 (3)	C9—C10—C11—N2	180.0
C5i—C1—C2—C2i	−0.5 (4)	C7—C6—C11—C10	0.000 (1)
S1—C1—C2—C2i	179.7 (2)	N1—C6—C11—C10	180.000 (1)
C2i—C2—C3—C4	−0.9 (4)	C7—C6—C11—N2	180.000 (1)
C1—C2—C3—C4	179.3 (2)	N1—C6—C11—N2	0.000 (1)
C2—C3—C4—C5	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.84	1.94	2.783 (6)	175
O1w—H1w···O2w	0.84	2.32	2.915 (6)	128
O1w—H1w···O2w′	0.84	2.19	2.799 (7)	130
O2w—H2w2···O3ii	0.84	2.35	2.873 (5)	121
O2w′—H2w4···O3ii	0.84	2.25	2.808 (6)	124
N1—H12···O1iii	0.88	2.07	2.880 (3)	153
N1—H11···O2w′	0.88	2.03	2.816 (5)	149
N2—H22···O1	0.88	1.99	2.815 (3)	156
N2—H21···O1wiv	0.88	1.88	2.735 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.84	1.94	2.783 (6)	175
O1w—H1w⋯O2w	0.84	2.32	2.915 (6)	128
O1w—H1w⋯O2w′	0.84	2.19	2.799 (7)	130
O2w—H2w2⋯O3i	0.84	2.35	2.873 (5)	121
O2w′—H2w4⋯O3i	0.84	2.25	2.808 (6)	124
N1—H12⋯O1ii	0.88	2.07	2.880 (3)	153
N1—H11⋯O2w′	0.88	2.03	2.816 (5)	149
N2—H22⋯O1	0.88	1.99	2.815 (3)	156
N2—H21⋯O1wiii	0.88	1.88	2.735 (4)	164

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