2,2'-Bipyridin-1-ium 3-nitro-benzene-sulfonate.

In the title compound, C(10)H(9)N(2) (+)·C(6)H(4)NO(5)S(-), the dihedral angle between the aromatic rings of the cation is 9.42 (7)°. In the crystal, the anions and cations are linked by C-H⋯O and N-H⋯O hydrogen bonds, generating R(2) (1)(5) and R(4) (4)(14) rings, respectively. These hydrogen bonds also provide packing along [110].

Related literature

For 2,2′-bipyridinium, see: Grummt et al. (2004 ▶); Branowska et al. (2005 ▶); Zhang et al. (2007 ▶); Kavitha et al. (2006 ▶). For aromatic sulfonates, see: Sharma et al. (2004 ▶); Vembu et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H9N2 +·C6H4NO5S−

M = 359.36

Triclinic,

a = 5.9527 (3) Å

b = 7.4674 (3) Å

c = 17.8800 (7) Å

α = 79.085 (3)°

β = 89.121 (4)°

γ = 87.939 (3)°

V = 779.87 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.60 × 0.51 × 0.38 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32, Stoe & Cie, 2002 ▶) T min = 0.859, T max = 0.935

17821 measured reflections

3069 independent reflections

2997 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.05

3069 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.39 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003909/fj2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003909/fj2270Isup2.hkl

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

C10H9N2+·C6H4NO5S−	Z = 2
Mr = 359.36	F(000) = 372
Triclinic, P1	Dx = 1.529 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9527 (3) Å	Cell parameters from 3236 reflections
b = 7.4674 (3) Å	θ = 2.3–28.1°
c = 17.8800 (7) Å	µ = 0.24 mm−1
α = 79.085 (3)°	T = 296 K
β = 89.121 (4)°	Prism, colourless
γ = 87.939 (3)°	0.60 × 0.51 × 0.38 mm
V = 779.87 (6) Å3

Stoe IPDS II diffractometer	3069 independent reflections
Radiation source: fine-focus sealed tube	2997 reflections with I > 2σ(I)
plane graphite	Rint = 0.042
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.3°
rotation method scans	h = −7→7
Absorption correction: integration (X-RED32, Stoe & Cie, 2002)	k = −9→9
Tmin = 0.859, Tmax = 0.935	l = −22→22
17821 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.2343P] where P = (Fo2 + 2Fc2)/3
3069 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.9249 (3)	0.6631 (2)	0.55700 (9)	0.0472 (3)
H1	0.7963	0.6145	0.5410	0.057*
C2	1.0720 (3)	0.7523 (2)	0.50459 (9)	0.0518 (4)
H2	1.0453	0.7652	0.4527	0.062*
C3	1.2602 (3)	0.8224 (2)	0.53019 (10)	0.0551 (4)
H3	1.3633	0.8815	0.4953	0.066*
C4	1.2977 (3)	0.8059 (2)	0.60717 (9)	0.0495 (4)
H4	1.4235	0.8563	0.6241	0.059*
C5	1.1473 (2)	0.71416 (19)	0.65879 (8)	0.0393 (3)
C6	1.1649 (2)	0.68668 (19)	0.74248 (8)	0.0399 (3)
C7	1.3558 (3)	0.7287 (2)	0.77801 (9)	0.0475 (4)
H7	1.4820	0.7711	0.7497	0.057*
C8	1.3540 (3)	0.7062 (2)	0.85644 (10)	0.0534 (4)
H8	1.4785	0.7354	0.8820	0.064*
C9	1.1657 (3)	0.6399 (2)	0.89627 (9)	0.0554 (4)
H9	1.1601	0.6244	0.9491	0.066*
C10	0.9862 (3)	0.5970 (2)	0.85640 (9)	0.0532 (4)
H10	0.8611	0.5490	0.8838	0.064*
C11	0.2858 (2)	0.1898 (2)	0.87745 (8)	0.0416 (3)
C12	0.4108 (2)	0.24262 (19)	0.81181 (8)	0.0383 (3)
H12	0.5512	0.2924	0.8135	0.046*
C13	0.3213 (2)	0.21927 (18)	0.74351 (8)	0.0362 (3)
C14	0.1093 (2)	0.1485 (2)	0.74167 (9)	0.0416 (3)
H14	0.0484	0.1353	0.6955	0.050*
C15	−0.0112 (2)	0.0977 (2)	0.80866 (10)	0.0475 (4)
H15	−0.1527	0.0497	0.8072	0.057*
C16	0.0758 (3)	0.1174 (2)	0.87731 (9)	0.0476 (4)
H16	−0.0047	0.0828	0.9224	0.057*
N1	0.9666 (2)	0.64630 (17)	0.63119 (7)	0.0415 (3)
N2	0.9811 (2)	0.62032 (18)	0.78077 (7)	0.0467 (3)
N3	0.3810 (3)	0.2146 (2)	0.94976 (7)	0.0536 (3)
O1	0.5688 (2)	0.2735 (2)	0.94961 (8)	0.0795 (5)
O2	0.2667 (3)	0.1770 (3)	1.00732 (8)	0.0897 (5)
O3	0.6150 (2)	0.42572 (17)	0.66965 (7)	0.0617 (3)
O4	0.3309 (2)	0.3147 (2)	0.59711 (7)	0.0657 (4)
O5	0.62591 (19)	0.11015 (17)	0.65774 (7)	0.0547 (3)
S1	0.48694 (6)	0.27252 (5)	0.659004 (19)	0.04088 (12)
H1A	0.875 (3)	0.581 (3)	0.6636 (12)	0.062 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0479 (8)	0.0537 (9)	0.0416 (8)	−0.0113 (7)	−0.0061 (6)	−0.0109 (6)
C2	0.0611 (10)	0.0582 (9)	0.0368 (8)	−0.0129 (8)	−0.0020 (7)	−0.0086 (7)
C3	0.0602 (10)	0.0616 (10)	0.0444 (9)	−0.0224 (8)	0.0095 (7)	−0.0093 (7)
C4	0.0476 (8)	0.0567 (9)	0.0473 (8)	−0.0203 (7)	0.0024 (7)	−0.0145 (7)
C5	0.0392 (7)	0.0404 (7)	0.0405 (7)	−0.0068 (6)	−0.0010 (6)	−0.0123 (6)
C6	0.0417 (7)	0.0395 (7)	0.0406 (7)	−0.0033 (6)	−0.0011 (6)	−0.0121 (6)
C7	0.0434 (8)	0.0533 (9)	0.0489 (9)	−0.0038 (7)	−0.0046 (7)	−0.0166 (7)
C8	0.0551 (9)	0.0565 (9)	0.0522 (9)	0.0040 (7)	−0.0161 (7)	−0.0191 (7)
C9	0.0696 (11)	0.0583 (10)	0.0394 (8)	0.0060 (8)	−0.0064 (8)	−0.0130 (7)
C10	0.0582 (10)	0.0587 (10)	0.0422 (8)	−0.0048 (8)	0.0049 (7)	−0.0085 (7)
C11	0.0433 (7)	0.0448 (8)	0.0365 (7)	0.0007 (6)	0.0016 (6)	−0.0077 (6)
C12	0.0339 (7)	0.0437 (7)	0.0381 (7)	−0.0040 (6)	0.0000 (5)	−0.0089 (6)
C13	0.0337 (6)	0.0380 (7)	0.0367 (7)	−0.0052 (5)	−0.0001 (5)	−0.0060 (5)
C14	0.0347 (7)	0.0449 (8)	0.0461 (8)	−0.0053 (6)	−0.0030 (6)	−0.0096 (6)
C15	0.0332 (7)	0.0481 (8)	0.0604 (10)	−0.0075 (6)	0.0055 (6)	−0.0080 (7)
C16	0.0436 (8)	0.0489 (8)	0.0486 (8)	−0.0032 (6)	0.0121 (7)	−0.0055 (7)
N1	0.0404 (6)	0.0464 (7)	0.0389 (6)	−0.0118 (5)	0.0005 (5)	−0.0087 (5)
N2	0.0470 (7)	0.0523 (7)	0.0417 (7)	−0.0082 (6)	0.0016 (5)	−0.0103 (5)
N3	0.0599 (9)	0.0650 (9)	0.0364 (7)	−0.0018 (7)	0.0023 (6)	−0.0109 (6)
O1	0.0639 (8)	0.1318 (14)	0.0470 (7)	−0.0203 (9)	−0.0070 (6)	−0.0242 (8)
O2	0.1000 (11)	0.1333 (14)	0.0388 (7)	−0.0341 (10)	0.0193 (7)	−0.0201 (8)
O3	0.0661 (7)	0.0675 (8)	0.0542 (7)	−0.0363 (6)	0.0115 (6)	−0.0130 (6)
O4	0.0549 (7)	0.1012 (10)	0.0376 (6)	−0.0137 (7)	−0.0108 (5)	−0.0014 (6)
O5	0.0484 (6)	0.0670 (7)	0.0517 (7)	−0.0053 (5)	0.0090 (5)	−0.0189 (5)
S1	0.03790 (19)	0.0538 (2)	0.03193 (18)	−0.01426 (15)	−0.00014 (13)	−0.00822 (14)

C1—N1	1.335 (2)	C10—H10	0.9300
C1—C2	1.367 (2)	C11—C16	1.380 (2)
C1—H1	0.9300	C11—C12	1.381 (2)
C2—C3	1.373 (2)	C11—N3	1.466 (2)
C2—H2	0.9300	C12—C13	1.383 (2)
C3—C4	1.379 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.3891 (19)
C4—C5	1.379 (2)	C13—S1	1.7798 (14)
C4—H4	0.9300	C14—C15	1.383 (2)
C5—N1	1.3446 (18)	C14—H14	0.9300
C5—C6	1.476 (2)	C15—C16	1.375 (2)
C6—N2	1.3413 (19)	C15—H15	0.9300
C6—C7	1.384 (2)	C16—H16	0.9300
C7—C8	1.380 (2)	N1—H1A	0.88 (2)
C7—H7	0.9300	N3—O1	1.2153 (19)
C8—C9	1.375 (3)	N3—O2	1.2180 (19)
C8—H8	0.9300	O3—S1	1.4406 (12)
C9—C10	1.374 (2)	O4—S1	1.4371 (12)
C9—H9	0.9300	O5—S1	1.4466 (12)
C10—N2	1.331 (2)
N1—C1—C2	119.67 (14)	C16—C11—N3	119.28 (13)
N1—C1—H1	120.2	C12—C11—N3	117.98 (13)
C2—C1—H1	120.2	C11—C12—C13	118.09 (13)
C1—C2—C3	118.59 (15)	C11—C12—H12	121.0
C1—C2—H2	120.7	C13—C12—H12	121.0
C3—C2—H2	120.7	C12—C13—C14	120.33 (13)
C2—C3—C4	120.66 (15)	C12—C13—S1	118.88 (10)
C2—C3—H3	119.7	C14—C13—S1	120.75 (11)
C4—C3—H3	119.7	C15—C14—C13	119.86 (14)
C5—C4—C3	119.53 (14)	C15—C14—H14	120.1
C5—C4—H4	120.2	C13—C14—H14	120.1
C3—C4—H4	120.2	C16—C15—C14	120.79 (14)
N1—C5—C4	117.78 (14)	C16—C15—H15	119.6
N1—C5—C6	116.68 (13)	C14—C15—H15	119.6
C4—C5—C6	125.53 (13)	C15—C16—C11	118.18 (14)
N2—C6—C7	123.11 (14)	C15—C16—H16	120.9
N2—C6—C5	114.67 (13)	C11—C16—H16	120.9
C7—C6—C5	122.21 (14)	C1—N1—C5	123.75 (13)
C8—C7—C6	118.32 (15)	C1—N1—H1A	117.7 (13)
C8—C7—H7	120.8	C5—N1—H1A	118.4 (13)
C6—C7—H7	120.8	C10—N2—C6	117.10 (14)
C9—C8—C7	119.08 (15)	O1—N3—O2	122.94 (16)
C9—C8—H8	120.5	O1—N3—C11	118.79 (13)
C7—C8—H8	120.5	O2—N3—C11	118.26 (15)
C10—C9—C8	118.62 (15)	O4—S1—O3	113.69 (8)
C10—C9—H9	120.7	O4—S1—O5	113.72 (8)
C8—C9—H9	120.7	O3—S1—O5	112.77 (8)
N2—C10—C9	123.73 (16)	O4—S1—C13	106.14 (7)
N2—C10—H10	118.1	O3—S1—C13	104.51 (7)
C9—C10—H10	118.1	O5—S1—C13	104.90 (7)
C16—C11—C12	122.74 (14)
N1—C1—C2—C3	0.0 (3)	C13—C14—C15—C16	0.4 (2)
C1—C2—C3—C4	−1.1 (3)	C14—C15—C16—C11	0.3 (2)
C2—C3—C4—C5	1.6 (3)	C12—C11—C16—C15	−0.1 (2)
C3—C4—C5—N1	−1.0 (2)	N3—C11—C16—C15	179.13 (14)
C3—C4—C5—C6	−179.67 (15)	C2—C1—N1—C5	0.6 (2)
N1—C5—C6—N2	−9.30 (19)	C4—C5—N1—C1	−0.1 (2)
C4—C5—C6—N2	169.42 (15)	C6—C5—N1—C1	178.68 (14)
N1—C5—C6—C7	171.48 (14)	C9—C10—N2—C6	1.2 (3)
C4—C5—C6—C7	−9.8 (2)	C7—C6—N2—C10	0.8 (2)
N2—C6—C7—C8	−2.0 (2)	C5—C6—N2—C10	−178.46 (13)
C5—C6—C7—C8	177.20 (14)	C16—C11—N3—O1	177.87 (16)
C6—C7—C8—C9	1.3 (2)	C12—C11—N3—O1	−2.9 (2)
C7—C8—C9—C10	0.5 (3)	C16—C11—N3—O2	−2.9 (2)
C8—C9—C10—N2	−1.8 (3)	C12—C11—N3—O2	176.31 (16)
C16—C11—C12—C13	−0.8 (2)	C12—C13—S1—O4	−154.95 (12)
N3—C11—C12—C13	179.98 (13)	C14—C13—S1—O4	27.62 (14)
C11—C12—C13—C14	1.5 (2)	C12—C13—S1—O3	−34.49 (13)
C11—C12—C13—S1	−175.98 (11)	C14—C13—S1—O3	148.08 (12)
C12—C13—C14—C15	−1.3 (2)	C12—C13—S1—O5	84.36 (12)
S1—C13—C14—C15	176.12 (11)	C14—C13—S1—O5	−93.07 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4i	0.93	2.55	3.1426 (19)	122
C2—H2···O4i	0.93	2.55	3.142 (2)	122
C4—H4···O5ii	0.93	2.45	3.3089 (19)	153
N1—H1A···O3	0.88 (2)	1.95 (2)	2.7096 (16)	142.9 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4i	0.93	2.55	3.1426 (19)	122
C2—H2⋯O4i	0.93	2.55	3.142 (2)	122
C4—H4⋯O5ii	0.93	2.45	3.3089 (19)	153
N1—H1A⋯O3	0.88 (2)	1.95 (2)	2.7096 (16)	142.9 (18)

Symmetry codes: (i) ; (ii) .