4-Amino-pyridinium 2-chloro-4-nitro-benzoate monohydrate.

In the title hydrated mol-ecular salt, C5H7N2(+)·C7H3ClNO4(-)·H2O, the ions and water mol-ecules assemble into ribbons of R6(5)(22) rings along the c axis via O(water)-H⋯O(-), N(+)-H⋯O(water) and N-H⋯O(-) hydrogen bonds. N-H⋯O(-) hydrogen bonds connect adjacent ribbons along the c-axis direction via R4(4)(12) rings, forming hydrogen-bonded layers. The CO2 and NO2 groups make dihedral angles of 81.8 (2) and 1.4 (2)°, respectively, with the ring in the anion.

Related literature

For related structures, see: Lemmerer et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H7N2 +·C7H3ClNO4 −·H2O

M = 313.7

Monoclinic,

a = 14.4500 (5) Å

b = 14.3300 (5) Å

c = 6.9918 (2) Å

β = 97.804 (2)°

V = 1434.37 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.78 × 0.31 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: integration (XPREP; Bruker, 2004 ▶) T min = 0.896, T max = 0.977

14928 measured reflections

3456 independent reflections

2685 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.04

3456 reflections

210 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.5 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker 2004 ▶); 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 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812046077/fy2073sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046077/fy2073Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046077/fy2073Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046077/fy2073Isup4.cml

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

C5H7N2+·C7H3ClNO4−·H2O	F(000) = 648
Mr = 313.7	Dx = 1.453 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4262 reflections
a = 14.4500 (5) Å	θ = 2.8–27.8°
b = 14.3300 (5) Å	µ = 0.29 mm−1
c = 6.9918 (2) Å	T = 173 K
β = 97.804 (2)°	Plate, colourless
V = 1434.37 (8) Å3	0.78 × 0.31 × 0.09 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2685 reflections with I > 2σ(I)
ω scans	Rint = 0.061
Absorption correction: integration (XPREP; Bruker, 2004)	θmax = 28°, θmin = 1.4°
Tmin = 0.896, Tmax = 0.977	h = −19→19
14928 measured reflections	k = −18→18
3456 independent reflections	l = −8→9

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0662P)2 + 0.1397P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.5 e Å−3
3456 reflections	Δρmin = −0.36 e Å−3
210 parameters

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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.

	x	y	z	Uiso*/Ueq
C1	0.69246 (11)	0.61389 (11)	0.2594 (2)	0.0261 (3)
C2	0.61757 (12)	0.55610 (11)	0.2858 (2)	0.0271 (3)
C3	0.52758 (11)	0.57500 (11)	0.2008 (2)	0.0284 (3)
H3	0.4772	0.5348	0.2188	0.034*
C4	0.51347 (11)	0.65438 (12)	0.0887 (2)	0.0290 (4)
C5	0.58469 (12)	0.71419 (12)	0.0592 (2)	0.0325 (4)
H5	0.5725	0.7687	−0.0176	0.039*
C6	0.67437 (12)	0.69317 (12)	0.1438 (2)	0.0311 (4)
H6	0.7245	0.7332	0.1232	0.037*
C7	0.79130 (11)	0.59307 (11)	0.3515 (2)	0.0291 (3)
N1	0.41775 (10)	0.67644 (11)	0.0004 (2)	0.0349 (3)
O1	0.84325 (9)	0.55490 (9)	0.24589 (19)	0.0412 (3)
O2	0.81313 (9)	0.61801 (10)	0.52270 (17)	0.0424 (3)
O3	0.35519 (9)	0.62315 (10)	0.0282 (2)	0.0462 (3)
O4	0.40575 (10)	0.74821 (11)	−0.0962 (2)	0.0513 (4)
Cl1	0.63660 (3)	0.45679 (3)	0.42817 (7)	0.04119 (15)
C8	0.96351 (14)	0.15836 (13)	0.3659 (2)	0.0361 (4)
H8	1.0019	0.1049	0.3936	0.043*
C9	1.00312 (12)	0.24412 (13)	0.3780 (2)	0.0341 (4)
H9	1.0687	0.2506	0.4123	0.041*
C10	0.94613 (12)	0.32426 (12)	0.3393 (2)	0.0293 (4)
C11	0.84995 (12)	0.30971 (12)	0.2835 (2)	0.0309 (4)
H11	0.8095	0.3614	0.2527	0.037*
C12	0.81509 (13)	0.22161 (13)	0.2739 (2)	0.0352 (4)
H12	0.75	0.2124	0.237	0.042*
N2	0.87086 (12)	0.14714 (11)	0.3155 (2)	0.0357 (3)
N3	0.98294 (12)	0.40973 (11)	0.3540 (2)	0.0368 (4)
H2	0.8439 (17)	0.0887 (18)	0.322 (3)	0.061 (7)*
H3A	0.9432 (16)	0.4610 (15)	0.322 (3)	0.045 (6)*
H3B	1.0408 (17)	0.4127 (15)	0.391 (3)	0.048 (6)*
O1W	0.8108 (2)	0.52435 (14)	0.8618 (3)	0.1094 (11)
H1W	0.817 (2)	0.541 (2)	0.965 (5)	0.080 (10)*
H2W	0.806 (2)	0.562 (2)	0.781 (5)	0.096 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0257 (8)	0.0296 (8)	0.0228 (7)	0.0026 (6)	0.0032 (6)	−0.0001 (6)
C2	0.0310 (8)	0.0261 (8)	0.0245 (7)	0.0017 (6)	0.0048 (6)	0.0017 (6)
C3	0.0268 (8)	0.0306 (8)	0.0281 (8)	−0.0034 (6)	0.0046 (6)	−0.0036 (6)
C4	0.0241 (8)	0.0377 (9)	0.0244 (7)	0.0046 (6)	0.0007 (6)	−0.0018 (6)
C5	0.0319 (9)	0.0339 (9)	0.0312 (8)	0.0036 (7)	0.0030 (7)	0.0082 (7)
C6	0.0265 (9)	0.0340 (9)	0.0325 (8)	−0.0007 (7)	0.0033 (6)	0.0062 (7)
C7	0.0260 (8)	0.0281 (8)	0.0319 (8)	0.0004 (6)	−0.0007 (6)	0.0059 (6)
N1	0.0256 (8)	0.0466 (9)	0.0316 (7)	0.0043 (6)	−0.0001 (6)	−0.0049 (7)
O1	0.0307 (7)	0.0477 (8)	0.0437 (7)	0.0115 (6)	−0.0002 (5)	−0.0040 (6)
O2	0.0367 (7)	0.0580 (8)	0.0302 (6)	−0.0009 (6)	−0.0039 (5)	−0.0001 (6)
O3	0.0254 (7)	0.0589 (9)	0.0530 (8)	−0.0023 (6)	0.0004 (6)	−0.0042 (7)
O4	0.0382 (8)	0.0584 (9)	0.0541 (8)	0.0136 (7)	−0.0054 (6)	0.0154 (7)
Cl1	0.0433 (3)	0.0341 (2)	0.0463 (3)	0.00160 (18)	0.0065 (2)	0.01473 (18)
C8	0.0429 (11)	0.0369 (9)	0.0287 (8)	0.0107 (8)	0.0059 (7)	0.0010 (7)
C9	0.0295 (9)	0.0400 (10)	0.0323 (8)	0.0069 (7)	0.0027 (7)	0.0002 (7)
C10	0.0306 (9)	0.0360 (9)	0.0214 (7)	0.0035 (7)	0.0037 (6)	−0.0002 (6)
C11	0.0282 (9)	0.0381 (9)	0.0262 (8)	0.0056 (7)	0.0033 (6)	0.0018 (7)
C12	0.0316 (9)	0.0472 (10)	0.0266 (8)	−0.0011 (7)	0.0030 (7)	0.0004 (7)
N2	0.0440 (9)	0.0359 (8)	0.0275 (7)	−0.0008 (7)	0.0060 (6)	0.0002 (6)
N3	0.0289 (8)	0.0361 (8)	0.0435 (9)	0.0021 (7)	−0.0018 (7)	−0.0013 (7)
O1W	0.249 (4)	0.0447 (10)	0.0407 (10)	0.0464 (14)	0.0425 (14)	0.0092 (9)

C1—C2	1.395 (2)	C8—N2	1.347 (2)
C1—C6	1.398 (2)	C8—C9	1.353 (3)
C1—C7	1.515 (2)	C8—H8	0.95
C2—C3	1.381 (2)	C9—C10	1.418 (2)
C2—Cl1	1.7369 (16)	C9—H9	0.95
C3—C4	1.381 (2)	C10—N3	1.334 (2)
C3—H3	0.95	C10—C11	1.407 (2)
C4—C5	1.376 (2)	C11—C12	1.358 (2)
C4—N1	1.471 (2)	C11—H11	0.95
C5—C6	1.383 (2)	C12—N2	1.345 (2)
C5—H5	0.95	C12—H12	0.95
C6—H6	0.95	N2—H2	0.93 (3)
C7—O2	1.248 (2)	N3—H3A	0.94 (2)
C7—O1	1.248 (2)	N3—H3B	0.84 (2)
N1—O3	1.219 (2)	O1W—H1W	0.75 (3)
N1—O4	1.230 (2)	O1W—H2W	0.78 (4)
C2—C1—C6	118.13 (15)	O4—N1—C4	117.71 (15)
C2—C1—C7	122.05 (14)	N2—C8—C9	121.43 (16)
C6—C1—C7	119.83 (14)	N2—C8—H8	119.3
C3—C2—C1	121.91 (15)	C9—C8—H8	119.3
C3—C2—Cl1	118.28 (12)	C8—C9—C10	119.60 (17)
C1—C2—Cl1	119.80 (12)	C8—C9—H9	120.2
C4—C3—C2	117.63 (15)	C10—C9—H9	120.2
C4—C3—H3	121.2	N3—C10—C11	121.74 (16)
C2—C3—H3	121.2	N3—C10—C9	120.92 (16)
C5—C4—C3	122.84 (15)	C11—C10—C9	117.33 (16)
C5—C4—N1	118.88 (15)	C12—C11—C10	119.83 (16)
C3—C4—N1	118.27 (15)	C12—C11—H11	120.1
C4—C5—C6	118.46 (15)	C10—C11—H11	120.1
C4—C5—H5	120.8	N2—C12—C11	121.31 (17)
C6—C5—H5	120.8	N2—C12—H12	119.3
C5—C6—C1	121.02 (16)	C11—C12—H12	119.3
C5—C6—H6	119.5	C12—N2—C8	120.46 (16)
C1—C6—H6	119.5	C12—N2—H2	118.9 (15)
O2—C7—O1	126.79 (16)	C8—N2—H2	120.3 (15)
O2—C7—C1	116.89 (15)	C10—N3—H3A	118.3 (13)
O1—C7—C1	116.28 (14)	C10—N3—H3B	116.1 (15)
O3—N1—O4	124.01 (15)	H3A—N3—H3B	126 (2)
O3—N1—C4	118.28 (15)	H1W—O1W—H2W	117 (3)
C6—C1—C2—C3	0.4 (2)	C2—C1—C7—O1	99.31 (18)
C7—C1—C2—C3	−179.64 (14)	C6—C1—C7—O1	−80.7 (2)
C6—C1—C2—Cl1	179.99 (12)	C5—C4—N1—O3	−179.69 (15)
C7—C1—C2—Cl1	0.0 (2)	C3—C4—N1—O3	−0.8 (2)
C1—C2—C3—C4	−0.6 (2)	C5—C4—N1—O4	−0.2 (2)
Cl1—C2—C3—C4	179.75 (12)	C3—C4—N1—O4	178.68 (15)
C2—C3—C4—C5	0.1 (2)	N2—C8—C9—C10	0.8 (3)
C2—C3—C4—N1	−178.79 (14)	C8—C9—C10—N3	178.61 (16)
C3—C4—C5—C6	0.8 (3)	C8—C9—C10—C11	−1.9 (2)
N1—C4—C5—C6	179.59 (14)	N3—C10—C11—C12	−178.78 (16)
C4—C5—C6—C1	−1.0 (3)	C9—C10—C11—C12	1.8 (2)
C2—C1—C6—C5	0.5 (2)	C10—C11—C12—N2	−0.5 (2)
C7—C1—C6—C5	−179.52 (15)	C11—C12—N2—C8	−0.8 (2)
C2—C1—C7—O2	−82.6 (2)	C9—C8—N2—C12	0.6 (2)
C6—C1—C7—O2	97.40 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1Wi	0.93 (3)	1.72 (3)	2.641 (2)	170 (2)
N3—H3A···O1	0.94 (2)	1.99 (2)	2.926 (2)	171.1 (19)
N3—H3B···O2ii	0.84 (2)	2.16 (3)	2.982 (2)	165 (2)
O1W—H1W···O1iii	0.75 (3)	1.96 (3)	2.698 (2)	166 (3)
O1W—H2W···O2	0.78 (4)	1.99 (4)	2.729 (2)	158 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1W i	0.93 (3)	1.72 (3)	2.641 (2)	170 (2)
N3—H3A⋯O1	0.94 (2)	1.99 (2)	2.926 (2)	171.1 (19)
N3—H3B⋯O2ii	0.84 (2)	2.16 (3)	2.982 (2)	165 (2)
O1W—H1W⋯O1iii	0.75 (3)	1.96 (3)	2.698 (2)	166 (3)
O1W—H2W⋯O2	0.78 (4)	1.99 (4)	2.729 (2)	158 (3)

Symmetry codes: (i) ; (ii) ; (iii) .