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

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812018284

organic compounds

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Volume 68| Part 5| May 2012| Page o1574

doi:10.1107/S1600536812018284

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

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 23 April 2012; accepted 24 April 2012; online 28 April 2012)

In the title salt, C₆H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·CH₃OH·3H₂O, the cation lies on a mirror plane and the anion on a center of inversion. One lattice water molecule is located on a mirror plane, another is equally disordered over two sites. The methanol solvent molecule is disordered about a mirror plane. In the crystal, the cations, anions, water and methanol molecules 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

C₆H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·CH₄O·3H₂O
M_r = 482.52
Monoclinic, P 2₁ /m
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.176
S = 1.13
2503 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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) -x+1, -y+1, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z]$ ; (iii) x, y, z-1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018284/xu5520sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812018284/xu5520Isup3.cml

checkCIF report

Comment top

Naphthalene-1,5-disulfonic acid has been characterized as several diammonium salts, e.g., as the ethane-1,2-diammonium (Zhu et al., 2009), the piperizine-1,4-diium (Wei, 2011) derivatives. In the salt, C₆H₁₀N₂^2+.C₁₀H₆O₆S₂^2–.3H₂O^.CH₃OH (Scheme I, Fig. 1), the cation lies on a mirror plane and the anion on a center-of-inversion. The cation, anion, water and methanol molecules are linked by O–H···O hydrogen bonds to form a three-dimensional network (Table 1).

Related literature top

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

Experimental top

A methanol solution (5 ml) of 1,2-benzenediamine (1 mmol, 108 mg) was added to an aqueous solution (5 ml) of 1,5-naphthalenedisulfonic acid tetrahydrate (0.5 mmol, 180 mg). The mixture was heated at 343 K until the reactants dissolved completely. The solution was filtered; colorless crystals were isolated after several days.suitable for X-ray diffraction were isolated from the filtrate afterfour days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₆H₁₀N₂^2+.C₁₀H₆O₆S₂^2–.3H₂O^.CH₃OH at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The symmetry-related atoms of the anion are not labeled.

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

Crystal data top

C₆H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·CH₄O·3H₂O	F(000) = 508
M_r = 482.52	D_x = 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

Data collection top

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

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0909P)² + 0.6772P] where P = (F_o² + 2F_c²)/3
2503 reflections	(Δ/σ)_max = 0.001
174 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₆H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·CH₄O·3H₂O	V = 1052.8 (3) Å³
M_r = 482.52	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 8.1727 (15) Å	µ = 0.31 mm⁻¹
b = 13.681 (2) Å	T = 293 K
c = 9.5173 (15) Å	0.25 × 0.22 × 0.19 mm
β = 98.390 (5)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2503 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1935 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.943	R_int = 0.044
10378 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.13	Δρ_max = 0.85 e Å⁻³
2503 reflections	Δρ_min = −0.41 e Å⁻³
174 parameters

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

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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···O1w^iv	0.88	1.88	2.735 (4)	164

Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) x, −y+3/2, z; (iv) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₆H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·CH₄O·3H₂O
M_r	482.52
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	293
a, b, c (Å)	8.1727 (15), 13.681 (2), 9.5173 (15)
β (°)	98.390 (5)
V (Å³)	1052.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.926, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	10378, 2503, 1935
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.176, 1.13
No. of reflections	2503
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.41

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z; (iii) x, y, z−1.

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (Nos. 12511z023 and 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 td03), Heilongjiang University (Hdtd2010–04), and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12).

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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References

organic compounds

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