Crystal structure of 4,4′-bipyridine-1,1'-diium naphthalene-2,6-di­sulfonate dihydrate

Çevik, S.; Sarı, M.; Sarı, M.; Tunç, T.

doi:10.1107/S160053681401784X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o989-o990

doi:10.1107/S160053681401784X

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Crystal structure of 4,4′-bipyridine-1,1'-diium naphthalene-2,6-disulfonate dihydrate

Sabri Çevik,^a Musa Sarı,^b ^* Murat Sarı ^a and Tuncay Tunç ^c

^aDepartment of Chemistry, Faculty of Sciences, Afyon Kocatepe University, 03200 Afyonkarahisar, Turkey, ^bGazi University, Department of Physics Education, Beşevler 06500 Ankara, Turkey, and ^cAksaray University, Faculty of Education, 68100 Aksaray, Turkey
^*Correspondence e-mail: msari@gazi.edu.tr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 24 July 2014; accepted 2 August 2014; online 9 August 2014)

The title hydrated molecular organic salt, C₁₀H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O, crystallized with half a bipyridinium cation, half a naphthalene-2,6-disulfonate anion and a water molecule in the asymmetric unit. The whole cation and anion are generated by inversion symmetry, the inversion centers being at the center of the bridging C—C bond of the cation, and at the center of the fused C—C bond of the naphthalene group of the anion. In the crystal, the anions and cations stack alternately along the a axis with π–π interactions [inter-centroid distance = 3.491 (1) Å]. The anions are linked via O—H⋯O(sulfonate) hydrogen bonds involving two inversion-related water molecules, forming chains along [10-1]. These chains are bridged by bifurcated N—H⋯(O,O) hydrogen bonds, forming a three-dimensional framework structure. There are also C—H⋯O hydrogen bonds present, reinforcing the framework structure.

Keywords: crystal structure; molecular salt; bipyridine; nathphalenedisulfonate; dihydrate.

CCDC reference: 1006095

1. Related literature

For the use of 4,4′-bipyridine in the construction of metal-organic frameworks, see: Batten et al. (2012 ); Burd et al. (2012 ); Jeazet & Janiak (2012 ). For the use of naphthalene-2,6-disulfonate in the preparation of metal-organic frameworks, exploiting its different coordination modes, see: Zhao et al. (2013 ); Borodkin et al. (2013 ); Chen et al. (2001 ); Song et al. (2010 ); Pereira Silva et al. (2006 ).

2. Experimental

2.1. Crystal data

C₁₀H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O
M_r = 480.50
Monoclinic, P 2₁ /n
a = 7.4022 (2) Å
b = 10.9390 (3) Å
c = 12.6500 (4) Å
β = 99.908 (1)°
V = 1009.03 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.35 × 0.24 × 0.15 mm

2.2. Data collection

Bruker SMART BREEZE CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.912, T_max = 0.953
39553 measured reflections
2551 independent reflections
2340 reflections with I > 2σ(I)
R_int = 0.033

2.3. Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.103
S = 1.04
2551 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O1ⁱ	0.82 (3)	2.01 (3)	2.8293 (18)	176 (2)
O1W—H1B⋯O3ⁱⁱ	0.82 (3)	2.04 (3)	2.8484 (18)	172 (2)
N1—H3⋯O2ⁱⁱⁱ	0.86	2.55	3.0212 (18)	116
N1—H3⋯O1W^iv	0.86	1.98	2.7948 (19)	157
C1—H1⋯O1^v	0.93	2.51	3.1946 (17)	130
C10—H10⋯O1^vi	0.93	2.60	3.294 (2)	132
C11—H11⋯O2^vii	0.93	2.47	3.2036 (19)	136
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y+1, z+1; (iii) -x, -y, -z+1; (iv) x, y-1, z; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) x, y, z+1; (vii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 and SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009).

Supporting information

CCDC reference: 1006095

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681401784X/su2764sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401784X/su2764Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681401784X/su2764Isup3.cml

checkCIF report

Synthesis and crystallization top

The title compound was prepared by a hydrothermal reaction using a 23 ml Parr Teflon-lined acid digestion bomb, heated in a Nuve brand FN300 model programmable electric oven. A mixture of VOSO₄·xH₂O, naphthalene-2,6-dicarboxylic acid, 4,4'-bipyridine and water (in molar ratio 1:1:1:55.6 mmol) was placed in a 23 ml Parr Teflon-lined autoclave which was subsequently heated for 90 h inside the oven at 473 K. After, the acid digestion bomb was cooled to room temperature over a period of 4 h. Very-light-yellow–green prismatic single crystals of the title compound and a dark-green unidentified vanadium oxide powder were filtered from the light-blue–green mother liquor. The crystals were separated from the powder under an optical microscope. Analysis calculated for C₂₀H₂₀N₂O₈V₂: C 49.991, H 4.195, N 5.831, S 13.346%; found: C 48.670, H 3.929, N 5.857, S 13.670%. Selected FT–IR peaks between 1650 and 400 cm^-1: 1635 (m), 1624 (m), 1591 (m), 1591 (w), 1502 (w), 1487 (m), 1372 (m), 1333 (w), 1314 (w), 1276 (w), 1244 (m), 1210 (s, sh), 1200 (s), 1194 (s, sh), 1183 (m, sh), 1144 (m), 1092 (s), 1029 (s), 1005 (m), 979 (m), 914 (m), 832 (m), 791 (m), 706 (w), 665 (s), 656 (s), 618 (s), 554 (m), 546 (m), 507 (w), 440 (m), 411 (m) cm^-1. Thermogravimetric analysis results supported the X-ray single-crystal structure analysis by giving a 7.5% weight loss in the range 393–413 K, corresponding to two water molecules per molecular formula.

Refinement top

The water molecule H atoms were located in a difference Fourier map and freely refined. The N- and C-bound H atoms were placed geometrically and refined using a riding model, with N—H = 0.86 and C—H = 0.93 Å and with U_iso(H) = 1.2U_eq(N,C).

Related literature top

For the use of 4,4'-bipyridine in the construction of metal-organic frameworks, see: Batten et al. (2012); Burd et al. (2012); Jeazet & Janiak (2012). For the use of naphthalene-2,6-disulfonate in the preparation of metal-organic frameworks, exploiting its different coordination modes, see: Zhao et al. (2013); Borodkin et al. (2013); Chen et al. (2001); Song et al. (2010); Pereira Silva et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 and SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title hydrated molecular salt, with the atom labelling. Displacement ellipsoids are drawn at the 40% probability level. [Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+1.] The inversion related water molecule is not shown.
	Fig. 2. A view along the a axis of the crystal packing of the title compound, showing the hydrogen bonds as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonds have been omitted for clarity).

4,4'-Bipyridine-1,1'-diium naphthalene-2,6-disulfonate dihydrate top

Crystal data top

C₁₀H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O	F(000) = 500
M_r = 480.50	D_x = 1.581 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4022 (2) Å	Cell parameters from 39513 reflections
b = 10.9390 (3) Å	θ = 2.5–28.5°
c = 12.6500 (4) Å	µ = 0.32 mm⁻¹
β = 99.908 (1)°	T = 296 K
V = 1009.03 (5) Å³	Plate, colourless
Z = 2	0.35 × 0.24 × 0.15 mm

Data collection top

Bruker SMART BREEZE CCD diffractometer	2551 independent reflections
Radiation source: fine-focus sealed X-ray tube	2340 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
ω–scans	θ_max = 28.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −9→9
T_min = 0.912, T_max = 0.953	k = −14→14
39553 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: mixed
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0614P)² + 0.3867P] where P = (F_o² + 2F_c²)/3
2551 reflections	(Δ/σ)_max < 0.001
153 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₁₀N₂²⁺·C₁₀H₆O₆S₂²⁻·2H₂O	V = 1009.03 (5) Å³
M_r = 480.50	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4022 (2) Å	µ = 0.32 mm⁻¹
b = 10.9390 (3) Å	T = 296 K
c = 12.6500 (4) Å	0.35 × 0.24 × 0.15 mm
β = 99.908 (1)°

Data collection top

Bruker SMART BREEZE CCD diffractometer	2551 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	2340 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.953	R_int = 0.033
39553 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.41 e Å⁻³
2551 reflections	Δρ_min = −0.23 e Å⁻³
153 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
S1	0.21510 (4)	−0.06706 (3)	0.18311 (2)	0.02743 (12)
O1	0.14850 (17)	0.05494 (9)	0.15242 (9)	0.0398 (3)
O2	0.06807 (15)	−0.14963 (10)	0.19836 (9)	0.0421 (3)
O3	0.33036 (17)	−0.11776 (14)	0.11235 (9)	0.0513 (3)
C1	0.55029 (19)	0.16047 (12)	0.64530 (11)	0.0305 (3)
H1	0.5516	0.2306	0.6870	0.037*
C2	0.45657 (18)	0.15973 (11)	0.54200 (10)	0.0291 (3)
H2	0.3943	0.2295	0.5138	0.035*
C3	0.45389 (16)	0.05348 (10)	0.47790 (10)	0.0230 (2)
C4	0.35783 (17)	0.05061 (11)	0.37022 (10)	0.0254 (2)
H4	0.2972	0.1200	0.3400	0.030*
C5	0.35503 (17)	−0.05470 (11)	0.31137 (10)	0.0254 (3)
N1	0.30960 (19)	0.21624 (13)	0.91922 (12)	0.0454 (3)
H3	0.2627	0.1463	0.8994	0.054*
C6	0.46027 (17)	0.43924 (12)	0.98236 (11)	0.0282 (3)
C7	0.3717 (2)	0.41942 (15)	0.87696 (13)	0.0412 (3)
H7	0.3633	0.4821	0.8267	0.049*
C8	0.2972 (2)	0.30668 (18)	0.84798 (14)	0.0493 (4)
H8	0.2375	0.2935	0.7780	0.059*
C10	0.3922 (3)	0.23110 (15)	1.01926 (15)	0.0479 (4)
H10	0.3989	0.1662	1.0673	0.057*
C11	0.4686 (2)	0.34212 (14)	1.05306 (12)	0.0398 (3)
H11	0.5261	0.3519	1.1239	0.048*
O1W	0.23786 (19)	0.96590 (12)	0.89658 (11)	0.0447 (3)
H1A	0.126 (4)	0.958 (2)	0.8846 (19)	0.058 (7)*
H1B	0.275 (3)	0.940 (2)	0.957 (2)	0.061 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03049 (19)	0.02730 (19)	0.02227 (18)	−0.00197 (11)	−0.00176 (12)	−0.00094 (10)
O1	0.0471 (6)	0.0292 (5)	0.0372 (6)	−0.0022 (4)	−0.0096 (5)	0.0062 (4)
O2	0.0435 (6)	0.0385 (6)	0.0391 (6)	−0.0158 (4)	−0.0076 (4)	0.0034 (4)
O3	0.0470 (7)	0.0765 (9)	0.0290 (5)	0.0134 (6)	0.0025 (5)	−0.0100 (5)
C1	0.0381 (7)	0.0221 (6)	0.0293 (6)	0.0007 (5)	0.0005 (5)	−0.0037 (5)
C2	0.0352 (6)	0.0200 (5)	0.0301 (6)	0.0036 (5)	−0.0003 (5)	0.0002 (5)
C3	0.0241 (5)	0.0198 (5)	0.0246 (6)	−0.0009 (4)	0.0024 (4)	0.0014 (4)
C4	0.0269 (6)	0.0217 (5)	0.0259 (6)	−0.0003 (4)	0.0002 (4)	0.0024 (4)
C5	0.0270 (6)	0.0258 (6)	0.0219 (6)	−0.0028 (4)	0.0001 (4)	0.0006 (4)
N1	0.0439 (7)	0.0390 (7)	0.0573 (8)	−0.0149 (6)	0.0200 (6)	−0.0172 (6)
C6	0.0250 (6)	0.0320 (7)	0.0291 (6)	−0.0030 (5)	0.0085 (5)	−0.0050 (5)
C7	0.0474 (9)	0.0421 (8)	0.0324 (7)	−0.0079 (6)	0.0019 (6)	−0.0050 (6)
C8	0.0510 (9)	0.0537 (10)	0.0417 (8)	−0.0144 (8)	0.0037 (7)	−0.0167 (7)
C10	0.0582 (10)	0.0366 (8)	0.0531 (10)	−0.0097 (7)	0.0217 (8)	0.0011 (7)
C11	0.0468 (8)	0.0393 (8)	0.0336 (7)	−0.0079 (6)	0.0081 (6)	0.0003 (6)
O1W	0.0425 (7)	0.0486 (7)	0.0417 (7)	−0.0014 (5)	0.0037 (5)	0.0042 (5)

Geometric parameters (Å, º) top

S1—O3	1.4489 (12)	N1—C10	1.317 (2)
S1—O1	1.4523 (11)	N1—C8	1.331 (3)
S1—O2	1.4525 (11)	N1—H3	0.8595
S1—C5	1.7735 (12)	C6—C11	1.383 (2)
C1—C2	1.3700 (18)	C6—C7	1.398 (2)
C1—C5ⁱ	1.4136 (17)	C6—C6ⁱⁱ	1.491 (2)
C1—H1	0.9300	C7—C8	1.375 (2)
C2—C3	1.4154 (17)	C7—H7	0.9300
C2—H2	0.9300	C8—H8	0.9300
C3—C3ⁱ	1.420 (2)	C10—C11	1.376 (2)
C3—C4	1.4244 (17)	C10—H10	0.9300
C4—C5	1.3698 (17)	C11—H11	0.9300
C4—H4	0.9300	O1W—H1A	0.82 (3)
C5—C1ⁱ	1.4135 (17)	O1W—H1B	0.82 (3)

O3—S1—O1	113.29 (8)	C1ⁱ—C5—S1	117.70 (9)
O3—S1—O2	112.23 (8)	C10—N1—C8	121.70 (14)
O1—S1—O2	112.29 (7)	C10—N1—H3	119.2
O3—S1—C5	106.32 (7)	C8—N1—H3	119.1
O1—S1—C5	107.01 (6)	C11—C6—C7	117.33 (13)
O2—S1—C5	105.01 (6)	C11—C6—C6ⁱⁱ	121.33 (16)
C2—C1—C5ⁱ	120.06 (11)	C7—C6—C6ⁱⁱ	121.33 (16)
C2—C1—H1	120.0	C8—C7—C6	119.63 (15)
C5ⁱ—C1—H1	120.0	C8—C7—H7	120.2
C1—C2—C3	120.41 (11)	C6—C7—H7	120.2
C1—C2—H2	119.8	N1—C8—C7	120.56 (15)
C3—C2—H2	119.8	N1—C8—H8	119.7
C2—C3—C3ⁱ	119.52 (14)	C7—C8—H8	119.7
C2—C3—C4	121.43 (11)	N1—C10—C11	120.35 (16)
C3ⁱ—C3—C4	119.05 (13)	N1—C10—H10	119.8
C5—C4—C3	119.78 (11)	C11—C10—H10	119.8
C5—C4—H4	120.1	C10—C11—C6	120.44 (15)
C3—C4—H4	120.1	C10—C11—H11	119.8
C4—C5—C1ⁱ	121.17 (11)	C6—C11—H11	119.8
C4—C5—S1	120.87 (9)	H1A—O1W—H1B	107 (2)

C5ⁱ—C1—C2—C3	−0.1 (2)	O1—S1—C5—C1ⁱ	−174.50 (11)
C1—C2—C3—C3ⁱ	1.3 (2)	O2—S1—C5—C1ⁱ	65.99 (12)
C1—C2—C3—C4	−179.84 (12)	C11—C6—C7—C8	0.2 (2)
C2—C3—C4—C5	−178.61 (12)	C6ⁱⁱ—C6—C7—C8	−178.78 (17)
C3ⁱ—C3—C4—C5	0.3 (2)	C10—N1—C8—C7	0.3 (3)
C3—C4—C5—C1ⁱ	−1.51 (19)	C6—C7—C8—N1	−0.4 (3)
C3—C4—C5—S1	172.51 (9)	C8—N1—C10—C11	0.1 (3)
O3—S1—C5—C4	132.64 (12)	N1—C10—C11—C6	−0.3 (3)
O1—S1—C5—C4	11.27 (13)	C7—C6—C11—C10	0.1 (2)
O2—S1—C5—C4	−108.24 (12)	C6ⁱⁱ—C6—C11—C10	179.13 (16)
O3—S1—C5—C1ⁱ	−53.13 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1ⁱⁱⁱ	0.82 (3)	2.01 (3)	2.8293 (18)	176 (2)
O1W—H1B···O3^iv	0.82 (3)	2.04 (3)	2.8484 (18)	172 (2)
N1—H3···O2^v	0.86	2.55	3.0212 (18)	116
N1—H3···O1W^vi	0.86	1.98	2.7948 (19)	157
C1—H1···O1^vii	0.93	2.51	3.1946 (17)	130
C10—H10···O1^viii	0.93	2.60	3.294 (2)	132
C11—H11···O2^ix	0.93	2.47	3.2036 (19)	136

Symmetry codes: (iii) −x, −y+1, −z+1; (iv) x, y+1, z+1; (v) −x, −y, −z+1; (vi) x, y−1, z; (vii) x+1/2, −y+1/2, z+1/2; (viii) x, y, z+1; (ix) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1ⁱ	0.82 (3)	2.01 (3)	2.8293 (18)	176 (2)
O1W—H1B···O3ⁱⁱ	0.82 (3)	2.04 (3)	2.8484 (18)	172 (2)
N1—H3···O2ⁱⁱⁱ	0.86	2.55	3.0212 (18)	116
N1—H3···O1W^iv	0.86	1.98	2.7948 (19)	157
C1—H1···O1^v	0.93	2.51	3.1946 (17)	130
C10—H10···O1^vi	0.93	2.60	3.294 (2)	132
C11—H11···O2^vii	0.93	2.47	3.2036 (19)	136

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

Acknowledgements

The authors acknowledge Afyon Kocatepe University (grant BAPK 09.FENED.03 of the University Research Fund) and Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010 K120480 of the State of Planning Organization).

References

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Volume 70| Part 9| September 2014| Pages o989-o990

doi:10.1107/S160053681401784X

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

Crystal structure of 4,4′-bi­pyridine-1,1'-diium naphthalene-2,6-di­sulfonate dihydrate

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′-bipyridine-1,1'-diium naphthalene-2,6-disulfonate dihydrate