Bis(butan-1-aminium) naphthalene-1,5-disulfonate

Jin, Y.

doi:10.1107/S1600536812018880

organic compounds

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Volume 68| Part 6| June 2012| Page o1595

doi:10.1107/S1600536812018880

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Bis(butan-1-aminium) naphthalene-1,5-disulfonate

Yu Jin ^a ^*

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

(Received 16 April 2012; accepted 26 April 2012; online 2 May 2012)

In the title compound, 2C₄H₁₂N⁺·C₁₀H₆O₆S₂²⁻, the anion lies on an inversion center, so the asymmetric unit contains half an anion and one cation which are linked by a strong N—H⋯O hydrogen bond. The crystal structure comprises discrete ions, which are linked into centrosymmetric R₄⁴(12) loops by N—H⋯O interactions.

Related literature

For related structures, see: Jin (2011a ,b , 2012 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

2C₄H₁₂N⁺·C₁₀H₆O₆S₂²⁻
M_r = 434.56
Monoclinic, P 2₁ /c
a = 8.1532 (16) Å
b = 9.2582 (19) Å
c = 14.108 (5) Å
β = 108.02 (3)°
V = 1012.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.30 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
10171 measured reflections
2316 independent reflections
2039 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.094
S = 1.14
2316 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.89	1.95	2.840 (2)	177
N1—H1C⋯O2ⁱ	0.89	1.97	2.857 (2)	177
N1—H1B⋯O3ⁱⁱ	0.89	2.05	2.911 (2)	162
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018880/bx2406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018880/bx2406Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018880/bx2406Isup3.cml

checkCIF report

Comment top

As an extension of the research about naphthalene-1,5-disulfonate salts (Jin, 2011a; Jin, 2011b; Jin, 2012), I report here the synthesis and the crystal structure of the title complex, 2C₄H₁₂N⁺C₁₀H₆S₂O₆^2-. In the title compound 2 C₄H₁₂N⁺. C₁₀H₆S₂O₆² , the anion lies on inversion center, so the asymmetric unit contains one-half anion and one cation which are linked by one strong N—H···O hydrogen bond interaction, Fig 1. The crystal structure comprises discrete ions which are linked into centrosymmetric R₄⁴(12) dimers by simple N—H···O interactions, (Bernstein, et al., 1995), Fig 2, Table1.

Related literature top

For related structures, see: Jin (2011a,b, 2012). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

2C₄H₁₂N⁺•C₁₀H₆S₂O₆^2- was synthetized from a mixture of CH₃(CH₂)₃NH₂ (146.28 mg, 2.00 mmol), C₁₀H₈O₆S₂ (288.28 mg, 1.00 mmol), and distilled water (10 ml), which was stirred a few minutes at room temperature, giving a clear transparent solution. After evaporation for a few days, block colorless crystals suitable for X-ray diffraction were obtained in about 88% yield and filtered and washed with distilled water.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound showing the labelling of the non-H atoms. Displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (a) 1-x, 2-y, 2-z]
	Fig. 2. Part of the crystal structure of (I) , showing discrete ions which are linked into centrosymmetric R₄⁴(12) dimers.[Symmetry codes : (i) x, 3/2-y, -1/2+z; (ii) -x, 1/2+y, 3/2-z; (iii) -x,2-y,1-z]

Bis(butan-1-aminium) naphthalene-1,5-disulfonate top

Crystal data top

2C₄H₁₂N⁺·C₁₀H₆O₆S₂²⁻	F(000) = 464
M_r = 434.56	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3450 reflections
a = 8.1532 (16) Å	θ = 6.2–55.3°
b = 9.2582 (19) Å	µ = 0.30 mm⁻¹
c = 14.108 (5) Å	T = 293 K
β = 108.02 (3)°	Block, colourless
V = 1012.7 (5) Å³	0.3 × 0.3 × 0.2 mm
Z = 2

Data collection top

Rigaku Mercury CCD diffractometer	2316 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −10→10
T_min = 0.489, T_max = 1.000	k = −12→12
10171 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0379P)² + 0.4216P] where P = (F_o² + 2F_c²)/3
2316 reflections	(Δ/σ)_max = 0.001
128 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

2C₄H₁₂N⁺·C₁₀H₆O₆S₂²⁻	V = 1012.7 (5) Å³
M_r = 434.56	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1532 (16) Å	µ = 0.30 mm⁻¹
b = 9.2582 (19) Å	T = 293 K
c = 14.108 (5) Å	0.3 × 0.3 × 0.2 mm
β = 108.02 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	2316 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2039 reflections with I > 2σ(I)
T_min = 0.489, T_max = 1.000	R_int = 0.034
10171 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.14	Δρ_max = 0.24 e Å⁻³
2316 reflections	Δρ_min = −0.43 e Å⁻³
128 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.2319 (2)	1.0297 (2)	0.69402 (14)	0.0364 (4)
H1D	0.2261	1.0939	0.7473	0.044*
H1E	0.2235	1.0880	0.6356	0.044*
C2	0.4015 (2)	0.95077 (19)	0.72490 (13)	0.0332 (4)
H2A	0.4062	0.8866	0.6714	0.040*
H2B	0.4085	0.8919	0.7829	0.040*
C3	0.5553 (3)	1.0519 (2)	0.74938 (15)	0.0405 (5)
H3A	0.5439	1.1157	0.6932	0.049*
H3B	0.5553	1.1112	0.8061	0.049*
C4	0.7256 (3)	0.9722 (3)	0.77313 (17)	0.0524 (6)
H4A	0.7286	0.9168	0.7161	0.079*
H4B	0.7376	0.9087	0.8286	0.079*
H4C	0.8186	1.0406	0.7896	0.079*
C5	0.2728 (2)	1.06642 (17)	0.97032 (12)	0.0253 (3)
H5	0.1617	1.0294	0.9555	0.030*
C6	0.41452 (18)	0.97062 (16)	0.98793 (11)	0.0198 (3)
C7	0.39614 (19)	0.81664 (16)	0.98343 (11)	0.0204 (3)
C8	0.5368 (2)	0.72878 (17)	1.00271 (12)	0.0259 (3)
H8	0.5228	0.6290	1.0009	0.031*
C9	0.2973 (2)	1.21166 (18)	0.97477 (13)	0.0286 (4)
H9	0.2025	1.2727	0.9627	0.034*
N1	0.0850 (2)	0.92591 (16)	0.67115 (11)	0.0338 (3)
H1A	0.0840	0.8815	0.7269	0.041*
H1B	−0.0136	0.9735	0.6455	0.041*
H1C	0.0971	0.8608	0.6274	0.041*
O1	0.09524 (16)	0.78595 (15)	0.85199 (9)	0.0380 (3)
O2	0.11042 (16)	0.77995 (14)	1.02545 (9)	0.0343 (3)
O3	0.21663 (16)	0.57911 (13)	0.95327 (10)	0.0353 (3)
S1	0.18812 (5)	0.73440 (4)	0.95082 (3)	0.02387 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0436 (11)	0.0273 (9)	0.0380 (10)	0.0057 (8)	0.0123 (8)	0.0024 (7)
C2	0.0409 (10)	0.0277 (9)	0.0313 (9)	0.0033 (7)	0.0118 (8)	−0.0002 (7)
C3	0.0491 (12)	0.0362 (10)	0.0351 (10)	−0.0046 (9)	0.0113 (9)	0.0010 (8)
C4	0.0407 (12)	0.0699 (16)	0.0470 (12)	−0.0053 (11)	0.0139 (10)	−0.0027 (11)
C5	0.0186 (7)	0.0255 (8)	0.0320 (8)	−0.0005 (6)	0.0078 (6)	0.0015 (6)
C6	0.0197 (7)	0.0203 (7)	0.0206 (7)	−0.0011 (6)	0.0081 (6)	0.0008 (5)
C7	0.0212 (7)	0.0202 (7)	0.0204 (7)	−0.0037 (6)	0.0073 (6)	0.0008 (6)
C8	0.0282 (8)	0.0166 (7)	0.0333 (8)	−0.0006 (6)	0.0101 (7)	0.0011 (6)
C9	0.0225 (8)	0.0235 (8)	0.0400 (9)	0.0052 (6)	0.0100 (7)	0.0025 (7)
N1	0.0363 (8)	0.0338 (8)	0.0320 (8)	0.0092 (6)	0.0116 (6)	0.0033 (6)
O1	0.0318 (7)	0.0443 (8)	0.0306 (7)	−0.0089 (6)	−0.0010 (5)	0.0079 (5)
O2	0.0315 (6)	0.0355 (7)	0.0417 (7)	−0.0059 (5)	0.0198 (6)	−0.0001 (5)
O3	0.0332 (7)	0.0219 (6)	0.0481 (8)	−0.0085 (5)	0.0084 (6)	−0.0019 (5)
S1	0.0220 (2)	0.0218 (2)	0.0267 (2)	−0.00585 (14)	0.00604 (15)	0.00118 (15)

Geometric parameters (Å, º) top

C1—N1	1.491 (2)	C5—H5	0.9300
C1—C2	1.505 (3)	C6—C7	1.433 (2)
C1—H1D	0.9700	C6—C6ⁱ	1.436 (3)
C1—H1E	0.9700	C7—C8	1.363 (2)
C2—C3	1.517 (3)	C7—S1	1.7847 (15)
C2—H2A	0.9700	C8—C9ⁱ	1.403 (2)
C2—H2B	0.9700	C8—H8	0.9300
C3—C4	1.516 (3)	C9—C8ⁱ	1.403 (2)
C3—H3A	0.9700	C9—H9	0.9300
C3—H3B	0.9700	N1—H1A	0.8900
C4—H4A	0.9600	N1—H1B	0.8900
C4—H4B	0.9600	N1—H1C	0.8900
C4—H4C	0.9600	O1—S1	1.4464 (14)
C5—C9	1.358 (2)	O2—S1	1.4493 (13)
C5—C6	1.416 (2)	O3—S1	1.4550 (13)

N1—C1—C2	110.73 (15)	C6—C5—H5	119.6
N1—C1—H1D	109.5	C5—C6—C7	123.16 (14)
C2—C1—H1D	109.5	C5—C6—C6ⁱ	118.93 (17)
N1—C1—H1E	109.5	C7—C6—C6ⁱ	117.91 (17)
C2—C1—H1E	109.5	C8—C7—C6	120.99 (14)
H1D—C1—H1E	108.1	C8—C7—S1	118.08 (12)
C1—C2—C3	112.76 (16)	C6—C7—S1	120.93 (11)
C1—C2—H2A	109.0	C7—C8—C9ⁱ	120.22 (15)
C3—C2—H2A	109.0	C7—C8—H8	119.9
C1—C2—H2B	109.0	C9ⁱ—C8—H8	119.9
C3—C2—H2B	109.0	C5—C9—C8ⁱ	121.16 (15)
H2A—C2—H2B	107.8	C5—C9—H9	119.4
C4—C3—C2	112.72 (18)	C8ⁱ—C9—H9	119.4
C4—C3—H3A	109.0	C1—N1—H1A	109.5
C2—C3—H3A	109.0	C1—N1—H1B	109.5
C4—C3—H3B	109.0	H1A—N1—H1B	109.5
C2—C3—H3B	109.0	C1—N1—H1C	109.5
H3A—C3—H3B	107.8	H1A—N1—H1C	109.5
C3—C4—H4A	109.5	H1B—N1—H1C	109.5
C3—C4—H4B	109.5	O1—S1—O2	112.83 (9)
H4A—C4—H4B	109.5	O1—S1—O3	112.40 (8)
C3—C4—H4C	109.5	O2—S1—O3	111.89 (8)
H4A—C4—H4C	109.5	O1—S1—C7	106.27 (8)
H4B—C4—H4C	109.5	O2—S1—C7	106.42 (8)
C9—C5—C6	120.77 (15)	O3—S1—C7	106.46 (7)
C9—C5—H5	119.6

N1—C1—C2—C3	−179.79 (15)	S1—C7—C8—C9ⁱ	177.76 (13)
C1—C2—C3—C4	−175.79 (16)	C6—C5—C9—C8ⁱ	−0.3 (3)
C9—C5—C6—C7	−179.48 (15)	C8—C7—S1—O1	−119.32 (13)
C9—C5—C6—C6ⁱ	0.9 (3)	C6—C7—S1—O1	59.88 (14)
C5—C6—C7—C8	−178.83 (15)	C8—C7—S1—O2	120.19 (13)
C6ⁱ—C6—C7—C8	0.8 (3)	C6—C7—S1—O2	−60.61 (14)
C5—C6—C7—S1	2.0 (2)	C8—C7—S1—O3	0.70 (15)
C6ⁱ—C6—C7—S1	−178.37 (13)	C6—C7—S1—O3	179.90 (12)
C6—C7—C8—C9ⁱ	−1.4 (2)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.89	1.95	2.840 (2)	177
N1—H1C···O2ⁱⁱ	0.89	1.97	2.857 (2)	177
N1—H1B···O3ⁱⁱⁱ	0.89	2.05	2.911 (2)	162

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

Experimental details

Crystal data
Chemical formula	2C₄H₁₂N⁺·C₁₀H₆O₆S₂²⁻
M_r	434.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1532 (16), 9.2582 (19), 14.108 (5)
β (°)	108.02 (3)
V (Å³)	1012.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.3 × 0.3 × 0.2

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.489, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10171, 2316, 2039
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.094, 1.14
No. of reflections	2316
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.43

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.89	1.95	2.840 (2)	176.9
N1—H1C···O2ⁱ	0.89	1.97	2.857 (2)	176.6
N1—H1B···O3ⁱⁱ	0.89	2.05	2.911 (2)	161.8

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

Acknowledgements

The author thanks Ordered Matter Science Research Center, Southeast University for its excellent experimental conditions and its generous financial support.

References

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