2-Amino-3-nitro-pyridinium 4-hy-droxy-benzene-sulfonate.

In the crystal structure of the title salt, C(5)H(6)N(3)O(2) (+)·C(6)H(5)O(4)S(-), N-H⋯O and O-H⋯O hydrogen bonds link the cations and anions. The dihedral angle between the rings of the cation and anion is 79.91 (6)°.

Related literature

For related structures, see: Nicoud et al. (1997 ▶); Akriche & Rzaigui (2009 ▶); Toumi Akriche et al. (2010 ▶); Koshima et al. (2004 ▶). For the design of second-order non-linear optical materials, see: Fur et al. (1998 ▶); Aakeröy et al. (1998 ▶). For information on the determination of non-linear optical properties, see: Kurtz & Perry (1968 ▶).

Experimental

Crystal data

C5H6N3O2 +·C6H5O4S−

M = 313.29

Monoclinic,

a = 9.0683 (19) Å

b = 13.5177 (16) Å

c = 10.9203 (17) Å

β = 94.042 (14)°

V = 1335.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.48 × 0.31 × 0.22 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.879, T max = 0.942

4067 measured reflections

2005 independent reflections

1989 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.063

S = 1.07

2005 reflections

194 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 825 Friedel pairs

Flack parameter: 0.05 (6)

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027651/pk2420sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027651/pk2420Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027651/pk2420Isup3.cml

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

C5H6N3O2+·C6H5O4S−	2-Amino-3-nitropyridine 4-hydroxybenzenesulfonate
Mr = 313.29	Dx = 1.558 Mg m−3
Monoclinic, Cc	Melting point: 481 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 9.0683 (19) Å	Cell parameters from 1991 reflections
b = 13.5177 (16) Å	θ = 3.0–27.5°
c = 10.9203 (17) Å	µ = 0.28 mm−1
β = 94.042 (14)°	T = 293 K
V = 1335.3 (4) Å3	Block, yellow
Z = 4	0.48 × 0.31 × 0.22 mm
F(000) = 648

Rigaku Mercury CCD diffractometer	2005 independent reflections
Radiation source: fine-focus sealed tube	1989 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
ω and φ scans'	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −10→10
Tmin = 0.879, Tmax = 0.942	k = −16→16
4067 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.3606P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2005 reflections	Δρmax = 0.12 e Å−3
194 parameters	Δρmin = −0.20 e Å−3
2 restraints	Absolute structure: Flack (1983), 825 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (6)

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
S1	0.61553 (5)	0.16714 (3)	0.00229 (4)	0.03441 (13)
O1	0.27111 (18)	0.05257 (12)	−0.51298 (15)	0.0525 (4)
O2	0.35055 (19)	0.09208 (11)	−0.68818 (14)	0.0566 (4)
O3	1.09361 (18)	−0.09220 (13)	0.20630 (15)	0.0517 (4)
O4	0.57072 (19)	0.22726 (11)	0.10356 (14)	0.0554 (5)
O5	0.49921 (15)	0.10255 (11)	−0.04791 (14)	0.0475 (4)
O6	0.67629 (17)	0.22667 (11)	−0.09397 (13)	0.0468 (4)
N1	0.4364 (2)	0.09853 (13)	−0.30840 (16)	0.0513 (5)
H1A	0.4637	0.1008	−0.2314	0.062*
H1B	0.3651	0.0603	−0.3342	0.062*
N2	0.35713 (19)	0.09660 (12)	−0.57633 (16)	0.0417 (4)
N3	0.61555 (19)	0.21303 (12)	−0.34220 (15)	0.0407 (4)
H3A	0.6404	0.2109	−0.2648	0.049*
C3	0.9047 (3)	−0.05629 (15)	0.0470 (2)	0.0453 (5)
H1C	0.9272	−0.1133	0.0045	0.054*
C4	0.9832 (2)	−0.03311 (14)	0.15597 (17)	0.0369 (4)
C10	0.6574 (3)	0.28190 (19)	−0.5342 (2)	0.0583 (6)
H3B	0.7071	0.3261	−0.5819	0.070*
C6	0.8393 (2)	0.11399 (14)	0.17267 (17)	0.0400 (5)
H4A	0.8172	0.1712	0.2149	0.048*
C11	0.6903 (3)	0.27529 (18)	−0.4120 (2)	0.0514 (6)
H5A	0.7657	0.3142	−0.3753	0.062*
C9	0.5476 (3)	0.22104 (17)	−0.58661 (19)	0.0485 (5)
H6A	0.5247	0.2231	−0.6709	0.058*
C2	0.7930 (2)	0.00511 (15)	0.00116 (18)	0.0417 (5)
H7A	0.7403	−0.0106	−0.0724	0.050*
C7	0.5037 (2)	0.15357 (14)	−0.38655 (17)	0.0356 (4)
C8	0.4725 (2)	0.15784 (13)	−0.51561 (17)	0.0348 (4)
C5	0.9519 (2)	0.05312 (16)	0.21828 (18)	0.0451 (5)
H10A	1.0069	0.0697	0.2905	0.054*
C1	0.7585 (2)	0.09035 (13)	0.06404 (17)	0.0303 (4)
H3	1.099 (3)	−0.136 (2)	0.164 (3)	0.073 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0370 (3)	0.0340 (2)	0.0317 (2)	0.0036 (2)	−0.00145 (17)	0.00220 (19)
O1	0.0457 (9)	0.0554 (9)	0.0561 (10)	−0.0104 (7)	0.0020 (8)	−0.0067 (8)
O2	0.0704 (12)	0.0594 (9)	0.0378 (8)	0.0024 (8)	−0.0123 (8)	−0.0111 (7)
O3	0.0527 (10)	0.0561 (9)	0.0451 (8)	0.0195 (7)	−0.0039 (7)	0.0041 (7)
O4	0.0701 (12)	0.0529 (9)	0.0430 (9)	0.0280 (8)	0.0026 (8)	−0.0038 (7)
O5	0.0361 (8)	0.0538 (8)	0.0510 (9)	−0.0047 (6)	−0.0078 (7)	0.0087 (7)
O6	0.0572 (10)	0.0455 (8)	0.0361 (8)	−0.0100 (7)	−0.0073 (7)	0.0109 (6)
N1	0.0538 (11)	0.0628 (11)	0.0362 (9)	−0.0152 (9)	−0.0041 (8)	0.0116 (8)
N2	0.0412 (10)	0.0407 (9)	0.0418 (10)	0.0083 (7)	−0.0063 (8)	−0.0073 (7)
N3	0.0378 (10)	0.0541 (9)	0.0295 (8)	−0.0040 (7)	−0.0038 (7)	0.0022 (7)
C3	0.0538 (14)	0.0403 (10)	0.0411 (11)	0.0096 (9)	−0.0008 (10)	−0.0083 (9)
C4	0.0339 (11)	0.0417 (9)	0.0350 (10)	0.0063 (8)	0.0006 (8)	0.0049 (8)
C10	0.0507 (14)	0.0799 (16)	0.0439 (13)	−0.0221 (12)	0.0014 (10)	0.0151 (11)
C6	0.0438 (12)	0.0407 (10)	0.0345 (10)	0.0071 (8)	−0.0045 (9)	−0.0081 (8)
C11	0.0420 (12)	0.0671 (14)	0.0444 (12)	−0.0167 (11)	−0.0025 (10)	0.0023 (10)
C9	0.0490 (13)	0.0655 (14)	0.0304 (11)	−0.0046 (11)	−0.0022 (10)	0.0068 (10)
C2	0.0472 (12)	0.0412 (10)	0.0352 (10)	0.0068 (8)	−0.0081 (9)	−0.0083 (8)
C7	0.0335 (11)	0.0386 (9)	0.0341 (10)	0.0037 (7)	−0.0020 (8)	0.0016 (8)
C8	0.0303 (11)	0.0424 (9)	0.0312 (9)	0.0028 (7)	−0.0017 (8)	0.0002 (7)
C5	0.0461 (13)	0.0551 (11)	0.0326 (10)	0.0060 (9)	−0.0067 (9)	−0.0069 (9)
C1	0.0305 (10)	0.0322 (8)	0.0281 (9)	0.0021 (7)	0.0019 (7)	0.0017 (7)

S1—O5	1.4470 (15)	C3—C4	1.379 (3)
S1—O4	1.4532 (15)	C3—H1C	0.9300
S1—O6	1.4622 (15)	C4—C5	1.389 (3)
S1—C1	1.7580 (19)	C10—C11	1.350 (3)
O1—N2	1.232 (2)	C10—C9	1.384 (3)
O2—N2	1.220 (2)	C10—H3B	0.9300
O3—C4	1.365 (2)	C6—C5	1.378 (3)
O3—H3	0.75 (3)	C6—C1	1.387 (3)
N1—C7	1.314 (2)	C6—H4A	0.9300
N1—H1A	0.8600	C11—H5A	0.9300
N1—H1B	0.8601	C9—C8	1.368 (3)
N2—C8	1.456 (2)	C9—H6A	0.9300
N3—C11	1.350 (3)	C2—C1	1.388 (3)
N3—C7	1.357 (2)	C2—H7A	0.9300
N3—H3A	0.8600	C7—C8	1.419 (3)
C3—C2	1.376 (3)	C5—H10A	0.9300
O5—S1—O4	112.97 (10)	C5—C6—C1	120.34 (18)
O5—S1—O6	111.18 (8)	C5—C6—H4A	119.8
O4—S1—O6	112.28 (8)	C1—C6—H4A	119.8
O5—S1—C1	106.70 (8)	N3—C11—C10	121.0 (2)
O4—S1—C1	106.05 (9)	N3—C11—H5A	119.5
O6—S1—C1	107.19 (9)	C10—C11—H5A	119.5
C4—O3—H3	107 (2)	C8—C9—C10	120.65 (19)
C7—N1—H1A	120.0	C8—C9—H6A	119.7
C7—N1—H1B	120.0	C10—C9—H6A	119.7
H1A—N1—H1B	120.0	C3—C2—C1	120.45 (17)
O2—N2—O1	123.34 (18)	C3—C2—H7A	119.8
O2—N2—C8	117.85 (19)	C1—C2—H7A	119.8
O1—N2—C8	118.80 (16)	N1—C7—N3	118.24 (16)
C11—N3—C7	124.10 (18)	N1—C7—C8	126.78 (17)
C11—N3—H3A	117.9	N3—C7—C8	114.98 (17)
C7—N3—H3A	117.9	C9—C8—C7	121.06 (18)
C2—C3—C4	119.90 (18)	C9—C8—N2	117.87 (17)
C2—C3—H1C	120.1	C7—C8—N2	121.05 (17)
C4—C3—H1C	120.1	C6—C5—C4	119.74 (17)
O3—C4—C3	122.25 (18)	C6—C5—H10A	120.1
O3—C4—C5	117.58 (18)	C4—C5—H10A	120.1
C3—C4—C5	120.17 (17)	C6—C1—C2	119.37 (17)
C11—C10—C9	118.2 (2)	C6—C1—S1	121.52 (15)
C11—C10—H3B	120.9	C2—C1—S1	119.10 (14)
C9—C10—H3B	120.9
C2—C3—C4—O3	179.0 (2)	O2—N2—C8—C7	−168.96 (18)
C2—C3—C4—C5	−1.4 (3)	O1—N2—C8—C7	11.4 (3)
C7—N3—C11—C10	−0.3 (4)	C1—C6—C5—C4	−1.0 (3)
C9—C10—C11—N3	−1.8 (4)	O3—C4—C5—C6	−178.49 (19)
C11—C10—C9—C8	1.6 (4)	C3—C4—C5—C6	1.9 (3)
C4—C3—C2—C1	−0.1 (3)	C5—C6—C1—C2	−0.5 (3)
C11—N3—C7—N1	−177.9 (2)	C5—C6—C1—S1	−179.21 (16)
C11—N3—C7—C8	2.4 (3)	C3—C2—C1—C6	1.0 (3)
C10—C9—C8—C7	0.6 (3)	C3—C2—C1—S1	179.78 (18)
C10—C9—C8—N2	179.3 (2)	O5—S1—C1—C6	−141.59 (17)
N1—C7—C8—C9	177.7 (2)	O4—S1—C1—C6	−20.9 (2)
N3—C7—C8—C9	−2.6 (3)	O6—S1—C1—C6	99.23 (19)
N1—C7—C8—N2	−0.9 (3)	O5—S1—C1—C2	39.69 (19)
N3—C7—C8—N2	178.80 (16)	O4—S1—C1—C2	160.38 (17)
O2—N2—C8—C9	12.3 (3)	O6—S1—C1—C2	−79.49 (18)
O1—N2—C8—C9	−167.30 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5	0.86	2.01	2.862 (2)	172
N1—H1B···O1	0.86	2.08	2.674 (2)	126
N3—H3A···O6	0.86	1.88	2.734 (2)	170
N1—H1B···O3i	0.86	2.57	3.125 (3)	123
O3—H3···O4ii	0.75 (3)	1.98 (3)	2.688 (2)	158 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5	0.86	2.01	2.862 (2)	172
N1—H1B⋯O1	0.86	2.08	2.674 (2)	126
N3—H3A⋯O6	0.86	1.88	2.734 (2)	170
N1—H1B⋯O3i	0.86	2.57	3.125 (3)	123
O3—H3⋯O4ii	0.75 (3)	1.98 (3)	2.688 (2)	158 (3)

Symmetry codes: (i) ; (ii) .