4-Nitro-N-(4-pyridinio)benzene-sulfonamidate monohydrate.

The title compound, C(11)H(9)N(3)O(4)S·H(2)O, contains both an acid and a base centre, and displays a zwitterionic structure in the solid state. The benzene ring makes an angle of 109.1 (2)° with the pyridinium ring. The crystal structure is stabilized by O-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Allen et al. (1987 ▶); Li et al. (2007 ▶); Damiano et al. (2007 ▶); Yu & Li (2007 ▶).

Experimental

Crystal data

C11H9N3O4S·H2O

M = 297.29

Monoclinic,

a = 6.7766 (14) Å

b = 8.3932 (17) Å

c = 21.717 (4) Å

β = 92.35 (3)°

V = 1234.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 113 (2) K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.932, T max = 0.963

9708 measured reflections

2908 independent reflections

2022 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.136

S = 1.17

2908 reflections

193 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032273/at2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032273/at2641Isup2.hkl

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

C11H9N3O4S·H2O	F(000) = 616
Mr = 297.29	Dx = 1.600 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3340 reflections
a = 6.7766 (14) Å	θ = 1.9–27.9°
b = 8.3932 (17) Å	µ = 0.29 mm−1
c = 21.717 (4) Å	T = 113 K
β = 92.35 (3)°	Block, colourless
V = 1234.2 (4) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	2908 independent reflections
Radiation source: rotating anode	2022 reflections with I > 2σ(I)
confocal	Rint = 0.061
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 1.9°
ω and φ scans	h = −8→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −11→10
Tmin = 0.932, Tmax = 0.963	l = −19→28
9708 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.031P)2 + 1.5168P] where P = (Fo2 + 2Fc2)/3
2908 reflections	(Δ/σ)max = 0.002
193 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.45 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
S1	0.89206 (11)	0.18818 (8)	0.12547 (3)	0.01574 (18)
N1	0.7145 (4)	0.7176 (3)	0.00969 (13)	0.0228 (6)
H1A	0.707 (6)	0.823 (5)	−0.0019 (19)	0.048 (12)*
N2	0.8061 (4)	0.2477 (3)	0.06005 (11)	0.0166 (5)
N3	0.2350 (4)	0.1341 (3)	0.29976 (12)	0.0236 (6)
O1	1.0378 (3)	0.2937 (2)	0.15368 (9)	0.0197 (5)
O2	0.9523 (3)	0.0240 (2)	0.11577 (10)	0.0208 (5)
O3	0.2477 (4)	0.2106 (3)	0.34777 (10)	0.0332 (6)
O4	0.0934 (4)	0.0497 (3)	0.28506 (13)	0.0401 (7)
C1	0.7738 (4)	0.4058 (3)	0.04742 (13)	0.0151 (6)
C2	0.7618 (5)	0.5312 (3)	0.09068 (14)	0.0203 (6)
H2	0.7736	0.5099	0.1336	0.024*
C3	0.7329 (5)	0.6835 (4)	0.06978 (16)	0.0259 (7)
H3	0.7257	0.7677	0.0989	0.031*
C4	0.7199 (5)	0.6006 (4)	−0.03300 (14)	0.0204 (6)
H4	0.7053	0.6265	−0.0755	0.024*
C5	0.7463 (4)	0.4454 (3)	−0.01543 (14)	0.0176 (6)
H5	0.7462	0.3638	−0.0458	0.021*
C6	0.6953 (4)	0.1762 (3)	0.17671 (13)	0.0150 (6)
C7	0.5306 (5)	0.0811 (3)	0.16067 (13)	0.0182 (6)
H7	0.5230	0.0275	0.1221	0.022*
C8	0.3798 (5)	0.0659 (3)	0.20114 (14)	0.0180 (6)
H8	0.2678	0.0013	0.1912	0.022*
C9	0.3961 (4)	0.1475 (3)	0.25685 (13)	0.0171 (6)
C10	0.5550 (5)	0.2447 (3)	0.27298 (14)	0.0199 (6)
H10	0.5598	0.3011	0.3109	0.024*
C11	0.7072 (5)	0.2580 (3)	0.23239 (13)	0.0189 (6)
H11	0.8189	0.3226	0.2426	0.023*
O5	0.7268 (4)	0.0224 (2)	−0.03361 (11)	0.0216 (5)
H5A	0.763 (6)	0.079 (5)	−0.003 (2)	0.046 (13)*
H5B	0.815 (7)	0.027 (5)	−0.060 (2)	0.049 (14)*

	U11	U22	U33	U12	U13	U23
S1	0.0176 (4)	0.0143 (3)	0.0154 (3)	0.0017 (3)	0.0016 (3)	0.0006 (3)
N1	0.0216 (15)	0.0139 (11)	0.0326 (15)	−0.0023 (10)	−0.0021 (12)	0.0047 (11)
N2	0.0213 (14)	0.0133 (11)	0.0152 (11)	0.0014 (10)	0.0005 (10)	0.0005 (9)
N3	0.0253 (15)	0.0227 (13)	0.0231 (14)	0.0026 (11)	0.0061 (12)	0.0037 (11)
O1	0.0175 (11)	0.0213 (10)	0.0203 (11)	−0.0013 (9)	−0.0007 (8)	−0.0004 (9)
O2	0.0254 (12)	0.0151 (10)	0.0222 (11)	0.0054 (8)	0.0056 (9)	0.0025 (8)
O3	0.0445 (16)	0.0358 (13)	0.0202 (11)	−0.0024 (11)	0.0134 (11)	−0.0026 (10)
O4	0.0294 (15)	0.0468 (15)	0.0452 (16)	−0.0171 (12)	0.0146 (13)	−0.0081 (13)
C1	0.0116 (15)	0.0138 (12)	0.0201 (14)	−0.0010 (10)	0.0029 (12)	0.0012 (11)
C2	0.0251 (17)	0.0172 (13)	0.0184 (14)	0.0024 (12)	−0.0027 (13)	−0.0017 (12)
C3	0.0309 (19)	0.0169 (14)	0.0292 (17)	0.0010 (13)	−0.0068 (14)	−0.0050 (13)
C4	0.0158 (16)	0.0244 (14)	0.0211 (15)	0.0013 (12)	0.0026 (12)	0.0048 (12)
C5	0.0135 (15)	0.0199 (13)	0.0196 (14)	0.0005 (11)	0.0037 (12)	−0.0003 (12)
C6	0.0155 (15)	0.0147 (12)	0.0148 (13)	0.0028 (11)	0.0008 (11)	0.0019 (11)
C7	0.0204 (16)	0.0189 (13)	0.0150 (13)	0.0013 (12)	−0.0024 (12)	−0.0021 (11)
C8	0.0164 (16)	0.0166 (13)	0.0207 (14)	0.0005 (11)	−0.0012 (12)	−0.0003 (12)
C9	0.0180 (15)	0.0170 (13)	0.0165 (14)	0.0022 (11)	0.0033 (12)	0.0033 (11)
C10	0.0241 (17)	0.0205 (13)	0.0151 (13)	0.0021 (12)	0.0000 (12)	−0.0035 (12)
C11	0.0221 (16)	0.0190 (13)	0.0156 (13)	−0.0026 (12)	−0.0008 (12)	−0.0012 (11)
O5	0.0292 (14)	0.0158 (10)	0.0199 (11)	−0.0026 (9)	0.0037 (10)	−0.0011 (9)

S1—O1	1.444 (2)	C4—C5	1.367 (4)
S1—O2	1.455 (2)	C4—H4	0.9500
S1—N2	1.594 (2)	C5—H5	0.9500
S1—C6	1.774 (3)	C6—C11	1.390 (4)
N1—C3	1.337 (4)	C6—C7	1.404 (4)
N1—C4	1.352 (4)	C7—C8	1.381 (4)
N1—H1A	0.92 (4)	C7—H7	0.9500
N2—C1	1.370 (3)	C8—C9	1.391 (4)
N3—O4	1.224 (4)	C8—H8	0.9500
N3—O3	1.225 (3)	C9—C10	1.385 (4)
N3—C9	1.468 (4)	C10—C11	1.388 (4)
C1—C5	1.410 (4)	C10—H10	0.9500
C1—C2	1.416 (4)	C11—H11	0.9500
C2—C3	1.368 (4)	O5—H5A	0.85 (4)
C2—H2	0.9500	O5—H5B	0.85 (5)
C3—H3	0.9500
O1—S1—O2	116.81 (13)	C5—C4—H4	119.8
O1—S1—N2	113.86 (13)	C4—C5—C1	120.4 (3)
O2—S1—N2	105.21 (12)	C4—C5—H5	119.8
O1—S1—C6	106.69 (13)	C1—C5—H5	119.8
O2—S1—C6	105.05 (13)	C11—C6—C7	120.9 (3)
N2—S1—C6	108.69 (13)	C11—C6—S1	120.0 (2)
C3—N1—C4	120.7 (3)	C7—C6—S1	119.1 (2)
C3—N1—H1A	118 (3)	C8—C7—C6	119.8 (3)
C4—N1—H1A	121 (3)	C8—C7—H7	120.1
C1—N2—S1	122.1 (2)	C6—C7—H7	120.1
O4—N3—O3	123.5 (3)	C7—C8—C9	118.2 (3)
O4—N3—C9	118.3 (3)	C7—C8—H8	120.9
O3—N3—C9	118.2 (3)	C9—C8—H8	120.9
N2—C1—C5	115.9 (2)	C10—C9—C8	122.9 (3)
N2—C1—C2	126.9 (3)	C10—C9—N3	118.4 (3)
C5—C1—C2	117.2 (3)	C8—C9—N3	118.7 (3)
C3—C2—C1	119.1 (3)	C9—C10—C11	118.5 (3)
C3—C2—H2	120.5	C9—C10—H10	120.8
C1—C2—H2	120.5	C11—C10—H10	120.8
N1—C3—C2	122.0 (3)	C10—C11—C6	119.6 (3)
N1—C3—H3	119.0	C10—C11—H11	120.2
C2—C3—H3	119.0	C6—C11—H11	120.2
N1—C4—C5	120.5 (3)	H5A—O5—H5B	109 (4)
N1—C4—H4	119.8
O1—S1—N2—C1	−36.5 (3)	O2—S1—C6—C7	−55.7 (3)
O2—S1—N2—C1	−165.6 (2)	N2—S1—C6—C7	56.5 (3)
C6—S1—N2—C1	82.3 (3)	C11—C6—C7—C8	−1.3 (4)
S1—N2—C1—C5	164.4 (2)	S1—C6—C7—C8	177.6 (2)
S1—N2—C1—C2	−16.8 (4)	C6—C7—C8—C9	0.5 (4)
N2—C1—C2—C3	178.6 (3)	C7—C8—C9—C10	1.0 (4)
C5—C1—C2—C3	−2.7 (5)	C7—C8—C9—N3	179.0 (3)
C4—N1—C3—C2	1.4 (5)	O4—N3—C9—C10	179.1 (3)
C1—C2—C3—N1	0.4 (5)	O3—N3—C9—C10	0.6 (4)
C3—N1—C4—C5	−0.6 (5)	O4—N3—C9—C8	0.9 (4)
N1—C4—C5—C1	−1.8 (5)	O3—N3—C9—C8	−177.6 (3)
N2—C1—C5—C4	−177.7 (3)	C8—C9—C10—C11	−1.7 (4)
C2—C1—C5—C4	3.4 (4)	N3—C9—C10—C11	−179.8 (3)
O1—S1—C6—C11	−1.5 (3)	C9—C10—C11—C6	1.0 (4)
O2—S1—C6—C11	123.1 (2)	C7—C6—C11—C10	0.5 (4)
N2—S1—C6—C11	−124.7 (2)	S1—C6—C11—C10	−178.3 (2)
O1—S1—C6—C7	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N2	0.85 (4)	1.97 (4)	2.813 (3)	167 (4)
O5—H5B···O2i	0.85 (5)	2.07 (5)	2.895 (3)	164 (4)
N1—H1A···O5ii	0.92 (4)	1.82 (4)	2.728 (3)	170 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯N2	0.85 (4)	1.97 (4)	2.813 (3)	167 (4)
O5—H5B⋯O2i	0.85 (5)	2.07 (5)	2.895 (3)	164 (4)
N1—H1A⋯O5ii	0.92 (4)	1.82 (4)	2.728 (3)	170 (4)

Symmetry codes: (i) ; (ii) .