Crystal structure of 4,4′-(ethene-1,2-di­yl)dipyridinium bis­(3-carb­oxy­benzene­sulfonate)

Wu, J.; Zhu, L.-G.

doi:10.1107/S1600536814022673

organic compounds

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Volume 70| Part 11| November 2014| Page o1170

doi:10.1107/S1600536814022673

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Crystal structure of 4,4′-(ethene-1,2-diyl)dipyridinium bis(3-carboxybenzenesulfonate)

Jing Wu ^a and Long-Guan Zhu ^a ^*

^aDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
^*Correspondence e-mail: chezlg@zju.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 October 2014; accepted 15 October 2014; online 18 October 2014)

In the title molecular salt, C₁₂H₁₂N₂²⁺·2C₇H₅O₅S⁻, the complete dication is generated by crystallographic inversion symmetry. In the anion, the sulfonic acid group is deprotonated and the dihedral angle between the planes of the carboxylic acid group and the benzene ring is 12.41 (11)°. In the crystal, the anions are linked into inversion dimers by pairs of O—H⋯O hydrogen bonds, which generate R₂²(16) loops. The dications link the anion dimers into [10-2] chains via N—H⋯O hydrogen bonds.

Keywords: crystal structure; 3-sulfobenzoate; 1,2-bis(pyridin-4-yl)ethylene; hydrogen bonding; 4,4′-(ethane-1,2-diyl)dipyridinium.

CCDC reference: 1029402

1. Related literature

For general background to salts of 1,2-bis(pyridin-4-yl)ethylene and sulfobenzoates and their applications, see: Ma & Zhu (2014 ); Zheng & Zhu (2014 ); Lesniewska et al. (2014 ); Danylyuk et al. (2010 ); Zhang & Zhu (2006 , 2007 ).

2. Experimental

2.1. Crystal data

C₁₂H₁₂N₂²⁺·2C₇H₅O₅S⁻
M_r = 586.58
Triclinic, $[P \overline 1]$
a = 7.4573 (5) Å
b = 7.8381 (6) Å
c = 11.3111 (9) Å
α = 85.525 (6)°
β = 86.634 (6)°
γ = 69.545 (7)°
V = 617.22 (8) Å³
Z = 1
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 170 K
0.43 × 0.29 × 0.18 mm

2.2. Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini Ultra CCD) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.888, T_max = 0.951
3834 measured reflections
2182 independent reflections
1899 reflections with I > 2σ(I)
R_int = 0.025

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 0.98
2182 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O3ⁱ	0.86 (1)	1.85 (1)	2.683 (2)	163 (3)
N1—H1A⋯O1ⁱⁱ	0.83 (1)	1.91 (1)	2.727 (2)	172 (4)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y-1, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1029402

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814022673/hb7296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022673/hb7296Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022673/hb7296Isup3.cml

checkCIF report

Comment top

Sulfobenzoate derivatives and their organic or coordination compounds are very interesting in material science, such as potential applications in fluorescence and catalytic fields (Ma & Zhu, 2014; Zheng & Zhu, 2014). Sulfobenzoates have two functional groups, sulfonate and carboxylate, and can coordinate to metal ions via versatile coordination modes or can form abundant hydrogen bonds due to they have five donors or acceptors. The 1,2-bis(pyridin-4-yl)ethylene derivatives have been widely used as bridge linkers in the coordination chemistry. several organic complexes with the 1,2-bis(pyridin-4-yl)ethylene and sulfobenzoate ligands have been reported, such as, 4,4'-ethylene-1,2-diyldipyridinium bis(4-carboxybenzenesulfonate) dihydrate (Zheng & Zhu, 2014), bis(4-(2-(pyridin-4-yl)vinyl)pyridinium) 4-sulfonatobenzoate trihydrate (Zhang & Zhu, 2006), and 4-(2-(pyridin-4-yl)ethenyl)pyridinium 2-carboxybenzenesulfonate (Zhang & Zhu, 2007). The title complound has 1:2 ratio of cation to anion without any water molecule (Fig. 1). The cation is protonated and the anion is partly deprotonated. Two pyridyl rings of the 4-(2-(pyridin-4-yl)ethenyl)pyridinium anion are coplanar and the whole cation is a big pi-conjugated system. Two anions are linked by O—H···O between sulfonate and carboxylate groups into a dimer and these anionic dimers interact with cations by N—H···O hydrogen bonds, generating a chain (Fig. 2).

Related literature top

For general background to salts of 1,2-bis(pyridin-4-yl)ethylene and sulfobenzoates and their applications, see: Ma & Zhu (2014); Zheng & Zhu (2014); Lesniewska et al. (2014); Danylyuk et al. (2010); Zhang & Zhu (2006, 2007).

Experimental top

A mixed solution of 3-sulfobenzoate sodium (0.224 g,1 mmol) in 10 ml CH₃OH and 1,2-bis(pyridin-4-yl)ethylene(0.091 g, 0.5 mmol) in 8 ml of CH₃CN was stirred for one hour and set aside for slow evaporation at room tempereture. After two days, yellow plates were obtained and collected by filtration.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. View of the asymmetry unit of (I) showing displacement ellipsoids at the 50% probability level. Symmetry code: (i) 2–x, –y, 1–z.

Fig. 2 The hydrogen-bonded chain of (I).

4,4'-(Ethene-1,2-diyl)dipyridinium bis(3-carboxybenzenesulfonate) top

Crystal data top

C₁₂H₁₂N₂²⁺·2C₇H₅O₅S⁻	Z = 1
M_r = 586.58	F(000) = 304
Triclinic, P1	D_x = 1.578 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4573 (5) Å	Cell parameters from 1621 reflections
b = 7.8381 (6) Å	θ = 3.3–29.4°
c = 11.3111 (9) Å	µ = 0.28 mm⁻¹
α = 85.525 (6)°	T = 170 K
β = 86.634 (6)°	Plate, yellow
γ = 69.545 (7)°	0.43 × 0.29 × 0.18 mm
V = 617.22 (8) Å³

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini Ultra CCD) diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	1899 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 25.1°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→8
T_min = 0.888, T_max = 0.951	k = −8→9
3834 measured reflections	l = −13→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0444P)² + 0.4291P] where P = (F_o² + 2F_c²)/3
2182 reflections	(Δ/σ)_max = 0.001
187 parameters	Δρ_max = 0.24 e Å⁻³
2 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₂H₁₂N₂²⁺·2C₇H₅O₅S⁻	γ = 69.545 (7)°
M_r = 586.58	V = 617.22 (8) Å³
Triclinic, P1	Z = 1
a = 7.4573 (5) Å	Mo Kα radiation
b = 7.8381 (6) Å	µ = 0.28 mm⁻¹
c = 11.3111 (9) Å	T = 170 K
α = 85.525 (6)°	0.43 × 0.29 × 0.18 mm
β = 86.634 (6)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini Ultra CCD) diffractometer	2182 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1899 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.951	R_int = 0.025
3834 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	2 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.24 e Å⁻³
2182 reflections	Δρ_min = −0.42 e Å⁻³
187 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET) (compiled Nov 17 2009,16:58:22) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.19563 (7)	1.18509 (7)	0.82396 (4)	0.02058 (17)
N1	1.2183 (2)	0.1796 (3)	0.13817 (15)	0.0249 (4)
H1A	1.254 (5)	0.198 (5)	0.0693 (13)	0.080*
O1	0.3295 (2)	1.2088 (2)	0.90567 (12)	0.0262 (3)
O2	0.0064 (2)	1.2254 (2)	0.87794 (13)	0.0297 (4)
O3	0.1989 (2)	1.2820 (2)	0.70976 (13)	0.0309 (4)
O4	0.6933 (2)	0.4749 (2)	0.56362 (13)	0.0313 (4)
O5	0.5777 (2)	0.7626 (2)	0.48846 (14)	0.0339 (4)
H5A	0.656 (4)	0.725 (5)	0.430 (2)	0.080*
C1	0.2852 (3)	0.9481 (3)	0.79837 (17)	0.0197 (4)
C2	0.2567 (3)	0.8244 (3)	0.88595 (18)	0.0242 (5)
H2	0.1840	0.8660	0.9543	0.029*
C3	0.3371 (3)	0.6395 (3)	0.87079 (19)	0.0271 (5)
H3	0.3179	0.5567	0.9291	0.032*
C4	0.4461 (3)	0.5766 (3)	0.76930 (19)	0.0258 (5)
H4	0.5019	0.4519	0.7603	0.031*
C5	0.4716 (3)	0.7008 (3)	0.68091 (17)	0.0206 (4)
C6	0.3908 (3)	0.8874 (3)	0.69538 (17)	0.0196 (4)
H6	0.4076	0.9706	0.6364	0.024*
C7	0.5925 (3)	0.6311 (3)	0.57261 (18)	0.0231 (5)
C8	1.0500 (3)	0.2889 (3)	0.31413 (18)	0.0246 (5)
H8	0.9812	0.3866	0.3592	0.029*
C9	1.0830 (3)	0.1109 (3)	0.36022 (17)	0.0204 (4)
C10	1.1909 (3)	−0.0318 (3)	0.29100 (18)	0.0233 (5)
H10	1.2187	−0.1522	0.3200	0.028*
C11	1.2553 (3)	0.0070 (3)	0.18050 (18)	0.0255 (5)
H11	1.3260	−0.0879	0.1338	0.031*
C12	1.1187 (3)	0.3205 (3)	0.20264 (19)	0.0269 (5)
H12	1.0961	0.4394	0.1719	0.032*
C13	1.0020 (3)	0.0799 (3)	0.47750 (18)	0.0228 (4)
H13	0.9494	0.1797	0.5238	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0253 (3)	0.0180 (3)	0.0175 (3)	−0.0069 (2)	0.00549 (19)	−0.0025 (2)
N1	0.0229 (9)	0.0334 (11)	0.0187 (9)	−0.0105 (8)	0.0001 (7)	−0.0006 (8)
O1	0.0315 (8)	0.0256 (8)	0.0249 (8)	−0.0138 (6)	0.0056 (6)	−0.0080 (6)
O2	0.0277 (8)	0.0274 (9)	0.0327 (9)	−0.0085 (7)	0.0088 (6)	−0.0058 (7)
O3	0.0460 (9)	0.0195 (8)	0.0206 (8)	−0.0048 (7)	0.0085 (6)	−0.0004 (6)
O4	0.0364 (9)	0.0205 (8)	0.0320 (9)	−0.0030 (7)	0.0022 (6)	−0.0070 (7)
O5	0.0473 (10)	0.0223 (8)	0.0260 (9)	−0.0066 (7)	0.0134 (7)	−0.0033 (7)
C1	0.0201 (10)	0.0190 (10)	0.0202 (10)	−0.0071 (8)	−0.0011 (7)	−0.0009 (8)
C2	0.0275 (11)	0.0283 (12)	0.0199 (11)	−0.0139 (9)	0.0025 (8)	−0.0023 (9)
C3	0.0338 (12)	0.0255 (12)	0.0248 (11)	−0.0153 (9)	0.0001 (9)	0.0047 (9)
C4	0.0311 (12)	0.0181 (11)	0.0291 (12)	−0.0094 (9)	−0.0012 (9)	−0.0030 (9)
C5	0.0199 (10)	0.0221 (11)	0.0211 (11)	−0.0084 (8)	−0.0025 (8)	−0.0025 (8)
C6	0.0224 (10)	0.0199 (11)	0.0180 (10)	−0.0091 (8)	0.0004 (8)	−0.0008 (8)
C7	0.0259 (11)	0.0218 (11)	0.0232 (11)	−0.0098 (9)	−0.0007 (8)	−0.0042 (9)
C8	0.0271 (11)	0.0228 (11)	0.0222 (11)	−0.0063 (9)	0.0012 (8)	−0.0042 (9)
C9	0.0177 (10)	0.0222 (11)	0.0205 (10)	−0.0056 (8)	−0.0024 (7)	−0.0029 (8)
C10	0.0233 (11)	0.0215 (11)	0.0235 (11)	−0.0059 (8)	0.0016 (8)	−0.0027 (9)
C11	0.0226 (11)	0.0289 (12)	0.0238 (11)	−0.0067 (9)	0.0013 (8)	−0.0074 (9)
C12	0.0269 (11)	0.0253 (12)	0.0282 (12)	−0.0089 (9)	−0.0030 (9)	0.0015 (9)
C13	0.0240 (11)	0.0213 (10)	0.0212 (11)	−0.0048 (8)	0.0025 (8)	−0.0060 (8)

Geometric parameters (Å, º) top

S1—O2	1.4426 (15)	C4—C5	1.392 (3)
S1—O3	1.4499 (15)	C4—H4	0.9300
S1—O1	1.4664 (15)	C5—C6	1.393 (3)
S1—C1	1.781 (2)	C5—C7	1.497 (3)
N1—C11	1.338 (3)	C6—H6	0.9300
N1—C12	1.339 (3)	C8—C12	1.370 (3)
N1—H1A	0.827 (10)	C8—C9	1.392 (3)
O4—C7	1.200 (3)	C8—H8	0.9300
O5—C7	1.327 (3)	C9—C10	1.395 (3)
O5—H5A	0.855 (10)	C9—C13	1.464 (3)
C1—C6	1.386 (3)	C10—C11	1.363 (3)
C1—C2	1.392 (3)	C10—H10	0.9300
C2—C3	1.381 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.386 (3)	C13—C13ⁱ	1.324 (4)
C3—H3	0.9300	C13—H13	0.9300

O2—S1—O3	113.77 (9)	C1—C6—C5	119.45 (18)
O2—S1—O1	111.53 (9)	C1—C6—H6	120.3
O3—S1—O1	112.10 (9)	C5—C6—H6	120.3
O2—S1—C1	107.31 (9)	O4—C7—O5	123.92 (19)
O3—S1—C1	106.65 (9)	O4—C7—C5	123.93 (19)
O1—S1—C1	104.84 (9)	O5—C7—C5	112.14 (17)
C11—N1—C12	121.56 (18)	C12—C8—C9	120.2 (2)
C11—N1—H1A	118 (3)	C12—C8—H8	119.9
C12—N1—H1A	120 (3)	C9—C8—H8	119.9
C7—O5—H5A	112 (2)	C8—C9—C10	118.08 (18)
C6—C1—C2	120.52 (19)	C8—C9—C13	119.46 (18)
C6—C1—S1	120.31 (15)	C10—C9—C13	122.45 (19)
C2—C1—S1	119.08 (15)	C11—C10—C9	119.4 (2)
C3—C2—C1	119.64 (19)	C11—C10—H10	120.3
C3—C2—H2	120.2	C9—C10—H10	120.3
C1—C2—H2	120.2	N1—C11—C10	121.0 (2)
C2—C3—C4	120.50 (19)	N1—C11—H11	119.5
C2—C3—H3	119.7	C10—C11—H11	119.5
C4—C3—H3	119.7	N1—C12—C8	119.7 (2)
C3—C4—C5	119.72 (19)	N1—C12—H12	120.1
C3—C4—H4	120.1	C8—C12—H12	120.1
C5—C4—H4	120.1	C13ⁱ—C13—C9	124.8 (2)
C4—C5—C6	120.14 (18)	C13ⁱ—C13—H13	117.6
C4—C5—C7	119.23 (18)	C9—C13—H13	117.6
C6—C5—C7	120.59 (18)

O2—S1—C1—C6	140.83 (16)	C7—C5—C6—C1	−177.69 (17)
O3—S1—C1—C6	18.56 (18)	C4—C5—C7—O4	−11.6 (3)
O1—S1—C1—C6	−100.47 (16)	C6—C5—C7—O4	166.22 (19)
O2—S1—C1—C2	−42.65 (18)	C4—C5—C7—O5	169.47 (18)
O3—S1—C1—C2	−164.92 (15)	C6—C5—C7—O5	−12.7 (3)
O1—S1—C1—C2	76.05 (17)	C12—C8—C9—C10	1.6 (3)
C6—C1—C2—C3	1.1 (3)	C12—C8—C9—C13	−177.52 (19)
S1—C1—C2—C3	−175.44 (15)	C8—C9—C10—C11	−1.8 (3)
C1—C2—C3—C4	0.2 (3)	C13—C9—C10—C11	177.25 (18)
C2—C3—C4—C5	−1.3 (3)	C12—N1—C11—C10	0.6 (3)
C3—C4—C5—C6	1.1 (3)	C9—C10—C11—N1	0.8 (3)
C3—C4—C5—C7	178.94 (18)	C11—N1—C12—C8	−0.9 (3)
C2—C1—C6—C5	−1.2 (3)	C9—C8—C12—N1	−0.2 (3)
S1—C1—C6—C5	175.28 (14)	C8—C9—C13—C13ⁱ	169.0 (2)
C4—C5—C6—C1	0.1 (3)	C10—C9—C13—C13ⁱ	−10.1 (4)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3ⁱⁱ	0.86 (1)	1.85 (1)	2.683 (2)	163 (3)
N1—H1A···O1ⁱⁱⁱ	0.83 (1)	1.91 (1)	2.727 (2)	172 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3ⁱ	0.855 (10)	1.854 (14)	2.683 (2)	163 (3)
N1—H1A···O1ⁱⁱ	0.827 (10)	1.907 (12)	2.727 (2)	172 (4)

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

Acknowledgements

We acknowledge support from the National Natural Science Foundation of China (grant No. 21073157).

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Volume 70| Part 11| November 2014| Page o1170

doi:10.1107/S1600536814022673

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

Crystal structure of 4,4′-(ethene-1,2-di­yl)dipyridinium bis­­(3-carb­­oxy­benzene­sulfonate)

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4,4′-(ethene-1,2-diyl)dipyridinium bis(3-carboxybenzenesulfonate)