1-(5-Amino-2,4-dinitro-phen-yl)pyridinium chloride monohydrate.

In the cation of the title hydrated salt, C(11)H(9)N(4)O(4) (+)·Cl(-)·H(2)O, the six-membered rings are inclined to each other at 79.0 (1)° and an intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, N-H⋯Cl hydrogen bonds link two cations and two anions into centrosymmetric group, and O-H⋯Cl hydrogen bonds involving the water mol-ecules further link these groups into chains in [101]. An O-H⋯O inter-action is also present. The water mol-ecule is disordered over two sets of sites in a 0.555 (13):0.445 (13) ratio.

Related literature

For applications of N-substituted pyridinium salts, see: Sliwa (1996 ▶); Ali et al. (2005 ▶); Chelossi et al. (2006 ▶); Azzouz et al. (2008 ▶). For related structures, see: Shmidt et al. (2005 ▶); Wojtas et al. (2006 ▶); Manickkam & Kalaivani (2011 ▶); Chernyshev et al. (2011 ▶); Sridevi & Kalaivani (2012 ▶).

Experimental

Crystal data

C11H9N4O4 +·Cl−·H2O

M = 314.69

Monoclinic,

a = 5.4312 (4) Å

b = 21.493 (2) Å

c = 11.3892 (9) Å

β = 92.362 (3)°

V = 1328.33 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.871, T max = 0.939

14754 measured reflections

3125 independent reflections

2288 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.112

S = 1.03

3125 reflections

224 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038834/cv5319sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038834/cv5319Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038834/cv5319Isup3.cml

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

C11H9N4O4+·Cl−·H2O	F(000) = 648
Mr = 314.69	Dx = 1.574 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4581 reflections
a = 5.4312 (4) Å	θ = 2.6–25.4°
b = 21.493 (2) Å	µ = 0.32 mm−1
c = 11.3892 (9) Å	T = 293 K
β = 92.362 (3)°	Block, red
V = 1328.33 (19) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3125 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 27.9°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→6
Tmin = 0.871, Tmax = 0.939	k = −28→28
14754 measured reflections	l = −11→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.2604P] where P = (Fo2 + 2Fc2)/3
3125 reflections	(Δ/σ)max = 0.001
224 parameters	Δρmax = 0.20 e Å−3
9 restraints	Δρmin = −0.27 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	Occ. (<1)
C1	0.3483 (3)	0.66419 (8)	0.10183 (14)	0.0449 (4)
H1	0.4780	0.6878	0.1336	0.054*
C2	0.3105 (3)	0.66065 (9)	−0.01760 (15)	0.0531 (4)
H2	0.4149	0.6814	−0.0671	0.064*
C3	0.1174 (4)	0.62626 (9)	−0.06342 (15)	0.0563 (5)
H3	0.0871	0.6242	−0.1443	0.068*
C4	−0.0302 (4)	0.59508 (11)	0.01082 (17)	0.0663 (6)
H4	−0.1607	0.5712	−0.0194	0.080*
C5	0.0137 (3)	0.59893 (10)	0.12967 (16)	0.0613 (5)
H5	−0.0855	0.5773	0.1803	0.074*
C6	0.2469 (3)	0.63860 (8)	0.29921 (13)	0.0403 (4)
C7	0.1136 (3)	0.67842 (8)	0.37070 (14)	0.0414 (4)
C8	0.1804 (3)	0.68200 (8)	0.48832 (14)	0.0441 (4)
H8	0.0915	0.7076	0.5370	0.053*
C9	0.3760 (3)	0.64842 (8)	0.53520 (13)	0.0432 (4)
C10	0.5080 (3)	0.60594 (8)	0.46686 (13)	0.0439 (4)
C11	0.4326 (3)	0.60318 (8)	0.34576 (14)	0.0446 (4)
H11	0.5138	0.5761	0.2969	0.054*
N2	−0.0913 (3)	0.71602 (7)	0.32853 (13)	0.0493 (4)
N1	0.1997 (2)	0.63388 (6)	0.17294 (11)	0.0404 (3)
N3	0.4403 (3)	0.65911 (7)	0.65862 (12)	0.0517 (4)
O1	−0.1404 (2)	0.71820 (7)	0.22235 (12)	0.0628 (4)
O2	−0.2092 (3)	0.74376 (8)	0.40064 (13)	0.0787 (5)
O3	0.3182 (3)	0.69609 (7)	0.71230 (11)	0.0676 (4)
O4	0.6154 (3)	0.63139 (8)	0.70329 (11)	0.0740 (4)
N4	0.6928 (3)	0.57003 (8)	0.50422 (14)	0.0560 (4)
O5	0.3996 (12)	0.4960 (2)	0.1460 (6)	0.0653 (17)	0.555 (13)
O5'	0.4978 (12)	0.5075 (2)	0.0942 (7)	0.0622 (16)	0.445 (13)
Cl1	0.88637 (9)	0.47657 (2)	0.30769 (4)	0.06455 (18)
H5A	0.274 (7)	0.487 (3)	0.196 (5)	0.15 (2)*	0.555 (13)
H5B	0.556 (4)	0.494 (4)	0.174 (5)	0.15 (2)*	0.555 (13)
H5C	0.520 (14)	0.481 (3)	0.156 (4)	0.08 (3)*	0.445 (13)
H5D	0.554 (9)	0.499 (3)	0.022 (2)	0.064 (16)*	0.445 (13)
H4A	0.747 (3)	0.5711 (10)	0.5766 (14)	0.063 (6)*
H4B	0.759 (4)	0.5437 (9)	0.4563 (18)	0.071 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0445 (9)	0.0485 (9)	0.0413 (8)	−0.0051 (7)	−0.0018 (7)	0.0032 (7)
C2	0.0619 (11)	0.0584 (11)	0.0389 (9)	−0.0033 (8)	0.0029 (8)	0.0053 (8)
C3	0.0658 (12)	0.0667 (12)	0.0356 (8)	0.0059 (9)	−0.0056 (8)	0.0004 (8)
C4	0.0556 (11)	0.0906 (15)	0.0512 (11)	−0.0181 (10)	−0.0147 (9)	−0.0037 (10)
C5	0.0503 (10)	0.0871 (15)	0.0460 (9)	−0.0243 (10)	−0.0043 (8)	0.0058 (9)
C6	0.0384 (8)	0.0504 (9)	0.0318 (7)	−0.0074 (7)	−0.0034 (6)	0.0046 (6)
C7	0.0376 (8)	0.0440 (9)	0.0423 (8)	−0.0045 (6)	−0.0038 (6)	0.0045 (7)
C8	0.0464 (9)	0.0448 (9)	0.0412 (8)	−0.0039 (7)	0.0016 (7)	0.0002 (7)
C9	0.0481 (9)	0.0496 (9)	0.0315 (7)	−0.0067 (7)	−0.0022 (6)	0.0051 (7)
C10	0.0417 (8)	0.0514 (9)	0.0380 (8)	−0.0035 (7)	−0.0038 (7)	0.0073 (7)
C11	0.0418 (8)	0.0567 (10)	0.0353 (8)	0.0023 (7)	−0.0001 (6)	0.0029 (7)
N2	0.0442 (8)	0.0472 (8)	0.0556 (9)	−0.0020 (6)	−0.0096 (7)	0.0005 (7)
N1	0.0377 (6)	0.0501 (8)	0.0328 (6)	−0.0028 (6)	−0.0047 (5)	0.0041 (5)
N3	0.0631 (9)	0.0549 (9)	0.0365 (7)	−0.0051 (7)	−0.0052 (7)	0.0035 (7)
O1	0.0581 (8)	0.0727 (9)	0.0557 (8)	0.0073 (6)	−0.0222 (6)	−0.0006 (7)
O2	0.0757 (10)	0.0902 (11)	0.0696 (9)	0.0342 (8)	−0.0052 (8)	−0.0106 (8)
O3	0.0897 (10)	0.0747 (9)	0.0384 (7)	0.0102 (8)	0.0017 (7)	−0.0052 (6)
O4	0.0846 (10)	0.0864 (11)	0.0486 (8)	0.0167 (8)	−0.0252 (7)	−0.0053 (7)
N4	0.0577 (9)	0.0683 (11)	0.0409 (8)	0.0125 (8)	−0.0111 (7)	0.0022 (8)
O5	0.066 (3)	0.075 (2)	0.054 (3)	0.0075 (19)	−0.014 (2)	−0.0065 (17)
O5'	0.057 (3)	0.079 (2)	0.050 (3)	0.0092 (19)	0.001 (2)	0.002 (2)
Cl1	0.0775 (3)	0.0563 (3)	0.0576 (3)	0.0081 (2)	−0.0250 (2)	0.0010 (2)

C1—N1	1.336 (2)	C8—H8	0.9300
C1—C2	1.369 (2)	C9—C10	1.414 (2)
C1—H1	0.9300	C9—N3	1.4528 (19)
C2—C3	1.369 (3)	C10—N4	1.323 (2)
C2—H2	0.9300	C10—C11	1.424 (2)
C3—C4	1.365 (3)	C11—H11	0.9300
C3—H3	0.9300	N2—O2	1.2176 (19)
C4—C5	1.367 (3)	N2—O1	1.2285 (18)
C4—H4	0.9300	N3—O4	1.2158 (19)
C5—N1	1.336 (2)	N3—O3	1.216 (2)
C5—H5	0.9300	N4—H4A	0.864 (15)
C6—C11	1.354 (2)	N4—H4B	0.874 (16)
C6—C7	1.403 (2)	O5—H5A	0.930 (19)
C6—N1	1.4540 (19)	O5—H5B	0.90 (2)
C7—C8	1.375 (2)	O5'—H5C	0.916 (19)
C7—N2	1.442 (2)	O5'—H5D	0.913 (19)
C8—C9	1.374 (2)
N1—C1—C2	120.36 (15)	C8—C9—C10	121.78 (14)
N1—C1—H1	119.8	C8—C9—N3	116.37 (15)
C2—C1—H1	119.8	C10—C9—N3	121.85 (14)
C3—C2—C1	119.33 (16)	N4—C10—C9	126.50 (15)
C3—C2—H2	120.3	N4—C10—C11	118.14 (16)
C1—C2—H2	120.3	C9—C10—C11	115.35 (14)
C4—C3—C2	119.29 (16)	C6—C11—C10	122.40 (16)
C4—C3—H3	120.4	C6—C11—H11	118.8
C2—C3—H3	120.4	C10—C11—H11	118.8
C3—C4—C5	120.05 (18)	O2—N2—O1	123.14 (15)
C3—C4—H4	120.0	O2—N2—C7	118.02 (14)
C5—C4—H4	120.0	O1—N2—C7	118.83 (15)
N1—C5—C4	119.83 (17)	C1—N1—C5	121.11 (14)
N1—C5—H5	120.1	C1—N1—C6	118.62 (13)
C4—C5—H5	120.1	C5—N1—C6	120.26 (13)
C11—C6—C7	120.64 (14)	O4—N3—O3	122.92 (14)
C11—C6—N1	116.52 (14)	O4—N3—C9	118.69 (15)
C7—C6—N1	122.83 (14)	O3—N3—C9	118.39 (15)
C8—C7—C6	118.53 (14)	C10—N4—H4A	121.1 (14)
C8—C7—N2	117.52 (15)	C10—N4—H4B	120.2 (15)
C6—C7—N2	123.95 (14)	H4A—N4—H4B	119 (2)
C9—C8—C7	121.18 (15)	H5A—O5—H5B	119 (3)
C9—C8—H8	119.4	H5A—O5—H5C	119 (5)
C7—C8—H8	119.4	H5C—O5'—H5D	122 (4)
N1—C1—C2—C3	0.7 (3)	N4—C10—C11—C6	−179.34 (16)
C1—C2—C3—C4	−1.4 (3)	C9—C10—C11—C6	−0.2 (2)
C2—C3—C4—C5	0.7 (3)	C8—C7—N2—O2	−7.3 (2)
C3—C4—C5—N1	0.8 (3)	C6—C7—N2—O2	172.42 (16)
C11—C6—C7—C8	1.9 (2)	C8—C7—N2—O1	173.29 (15)
N1—C6—C7—C8	−176.69 (14)	C6—C7—N2—O1	−6.9 (2)
C11—C6—C7—N2	−177.90 (15)	C2—C1—N1—C5	0.9 (3)
N1—C6—C7—N2	3.5 (2)	C2—C1—N1—C6	179.68 (16)
C6—C7—C8—C9	1.2 (2)	C4—C5—N1—C1	−1.6 (3)
N2—C7—C8—C9	−178.98 (14)	C4—C5—N1—C6	179.61 (18)
C7—C8—C9—C10	−3.9 (2)	C11—C6—N1—C1	−78.17 (19)
C7—C8—C9—N3	175.86 (15)	C7—C6—N1—C1	100.44 (18)
C8—C9—C10—N4	−177.62 (17)	C11—C6—N1—C5	100.64 (19)
N3—C9—C10—N4	2.6 (3)	C7—C6—N1—C5	−80.8 (2)
C8—C9—C10—C11	3.3 (2)	C8—C9—N3—O4	−178.50 (16)
N3—C9—C10—C11	−176.45 (14)	C10—C9—N3—O4	1.3 (2)
C7—C6—C11—C10	−2.4 (2)	C8—C9—N3—O3	0.6 (2)
N1—C6—C11—C10	176.28 (14)	C10—C9—N3—O3	−179.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O4	0.86 (2)	2.09 (2)	2.671 (2)	124 (2)
N4—H4B···Cl1	0.87 (2)	2.35 (2)	3.2162 (19)	171 (2)
N4—H4A···Cl1i	0.86 (2)	2.56 (2)	3.2268 (16)	135 (2)
O5—H5B···Cl1	0.90 (2)	2.34 (3)	3.187 (3)	158 (5)
O5—H5A···Cl1ii	0.93 (2)	2.51 (2)	3.429 (9)	169 (5)
O5′—H5D···O5iii	0.91 (2)	1.94 (3)	2.815 (16)	160 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O4	0.86 (2)	2.09 (2)	2.671 (2)	124 (2)
N4—H4B⋯Cl1	0.87 (2)	2.35 (2)	3.2162 (19)	171 (2)
N4—H4A⋯Cl1i	0.86 (2)	2.56 (2)	3.2268 (16)	135 (2)
O5—H5B⋯Cl1	0.90 (2)	2.34 (3)	3.187 (3)	158 (5)
O5—H5A⋯Cl1ii	0.93 (2)	2.51 (2)	3.429 (9)	169 (5)
O5′—H5D⋯O5iii	0.91 (2)	1.94 (3)	2.815 (16)	160 (5)

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