3-Amino­pyridinium 3,5-dinitro­benzoate monohydrate

Wei, L.-H.

doi:10.1107/S1600536807046740

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3-Aminopyridinium 3,5-dinitrobenzoate monohydrate

L.-H. Wei

In the title compound, C₅H₇N₂⁺·C₇H₃N₂O₆⁻·H₂O, the components are connected by N—H

O and O—H

O hydrogen bonds into an infinite two-dimensional network running parallel to the (10 $\overline{2}$ ) plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046740/hb2550sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046740/hb2550Isup2.hkl Contains datablock I

CCDC reference: 663845

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R factor = 0.045
wR factor = 0.116
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         16

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

This work continues our previous synthetic and structural studies of supramolecular salts (Wang & Wei, 2007). Herein we present the crystal structure of the title salt, (I).

The title salt contains one 3-aminopyridinium cation, one 3,5-dinitrobenzoate anion and one crystallization water molecule. These components are connected by N—H···O and O—H···O hydrogen bonds, in which the water oxygen atom, two nitrogen atoms of 3-aminopyridinium cation act as the hydrogen-bond acceptor and 3-aminopyridinium cation acts as the hydrogen-bond donor (Table 1). This results in an infinite two-dimensional network runing parallel to the plane (102) (Fig. 2).

Related literature top

For a related structure, see: Wang & Wei (2007).

Experimental top

A 5-ml ethanol soloution of 3-aminopyridine (1.0 mmol, 0.094 g) was added to an aqueous solution (25 ml) of 3,5-dinitrobenzoic acid (1.0 mmol, 0.210 g). The mixture was stirred for 10 minutes at 373 K. The solution was filtered, and the filtrate was kept at room temperature. After a week, yellow crystals of (I) were obtained.

Structure description top

This work continues our previous synthetic and structural studies of supramolecular salts (Wang & Wei, 2007). Herein we present the crystal structure of the title salt, (I).

For a related structure, see: Wang & Wei (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of (I) shoiwng part of a (102) sheet. Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in hydrogen bonds are omitted.

3-Aminopyridinium 3,5-dinitrobenzoate monohydrate top

Crystal data top

C₅H₇N₂⁺·C₇H₃N₂O₆⁻·H₂O	F(000) = 672
M_r = 324.26	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2386 reflections
a = 8.904 (2) Å	θ = 2.3–26°
b = 7.0683 (16) Å	µ = 0.13 mm⁻¹
c = 22.331 (5) Å	T = 298 K
β = 90.002 (3)°	Block, yellow
V = 1405.3 (5) Å³	0.40 × 0.11 × 0.09 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2743 independent reflections
Radiation source: fine-focus sealed tube	2110 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
T_min = 0.950, T_max = 0.989	k = −8→8
7329 measured reflections	l = −14→27

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0558P)² + 0.2499P] where P = (F_o² + 2F_c²)/3
2743 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.23 e Å⁻³
16 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₅H₇N₂⁺·C₇H₃N₂O₆⁻·H₂O	V = 1405.3 (5) Å³
M_r = 324.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.904 (2) Å	µ = 0.13 mm⁻¹
b = 7.0683 (16) Å	T = 298 K
c = 22.331 (5) Å	0.40 × 0.11 × 0.09 mm
β = 90.002 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2743 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2110 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.989	R_int = 0.022
7329 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	16 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.23 e Å⁻³
2743 reflections	Δρ_min = −0.18 e Å⁻³
220 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.37418 (18)	0.5123 (2)	0.56099 (7)	0.0332 (4)
C2	0.39107 (18)	0.3634 (2)	0.60046 (8)	0.0355 (4)
H2	0.3353	0.2532	0.5957	0.043*
C3	0.49144 (19)	0.3802 (2)	0.64695 (8)	0.0366 (4)
C4	0.57995 (19)	0.5379 (2)	0.65486 (8)	0.0389 (4)
H4	0.6487	0.5459	0.6861	0.047*
C5	0.56233 (19)	0.6822 (2)	0.61467 (8)	0.0372 (4)
C6	0.46031 (19)	0.6747 (2)	0.56834 (8)	0.0369 (4)
H6	0.4492	0.7767	0.5424	0.044*
C7	0.26189 (19)	0.4982 (2)	0.51025 (7)	0.0349 (4)
N1	0.50348 (18)	0.2256 (2)	0.69057 (7)	0.0469 (4)
N2	0.65549 (18)	0.8523 (2)	0.62170 (8)	0.0508 (4)
O1	0.23633 (16)	0.64928 (17)	0.48228 (6)	0.0499 (4)
O2	0.20429 (15)	0.34363 (17)	0.49949 (6)	0.0480 (4)
O3	0.41038 (18)	0.1002 (2)	0.68925 (7)	0.0700 (5)
O4	0.60686 (18)	0.2298 (2)	0.72611 (7)	0.0693 (5)
O5	0.74764 (18)	0.8530 (2)	0.66225 (8)	0.0729 (5)
O6	0.63675 (19)	0.9837 (2)	0.58748 (8)	0.0705 (5)
O7	0.1604 (2)	−0.0161 (2)	0.54961 (7)	0.0738 (5)
H7A	0.165 (3)	0.0858 (17)	0.5317 (9)	0.081 (5)*
H7B	0.174 (3)	−0.102 (2)	0.5251 (8)	0.079 (5)*
C8	−0.00521 (19)	0.4146 (3)	0.38708 (8)	0.0382 (4)
H8	0.0140	0.3229	0.4160	0.046*
C9	−0.09708 (18)	0.3720 (2)	0.33890 (8)	0.0361 (4)
C10	−0.1206 (2)	0.5150 (3)	0.29727 (8)	0.0415 (4)
H10	−0.1807	0.4919	0.2640	0.050*
C11	−0.0566 (2)	0.6896 (3)	0.30467 (9)	0.0456 (5)
H11	−0.0740	0.7846	0.2767	0.055*
C12	0.0329 (2)	0.7240 (3)	0.35310 (9)	0.0475 (5)
H12	0.0771	0.8420	0.3585	0.057*
N3	0.05566 (17)	0.5854 (2)	0.39239 (7)	0.0417 (4)
H3	0.114 (2)	0.611 (3)	0.4234 (7)	0.060 (6)*
N4	−0.15849 (18)	0.1961 (2)	0.33348 (7)	0.0526 (5)
H4A	−0.1402	0.1110	0.3601	0.063*
H4B	−0.2155	0.1701	0.3035	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0364 (9)	0.0323 (9)	0.0310 (9)	0.0002 (7)	0.0005 (7)	−0.0019 (7)
C2	0.0363 (9)	0.0357 (9)	0.0345 (9)	−0.0023 (7)	−0.0010 (7)	−0.0011 (8)
C3	0.0399 (9)	0.0378 (9)	0.0321 (9)	0.0040 (8)	−0.0020 (7)	0.0001 (8)
C4	0.0368 (9)	0.0442 (10)	0.0358 (10)	0.0041 (8)	−0.0074 (8)	−0.0103 (8)
C5	0.0364 (9)	0.0337 (9)	0.0414 (10)	−0.0021 (7)	0.0001 (8)	−0.0091 (8)
C6	0.0416 (10)	0.0328 (9)	0.0362 (10)	0.0012 (7)	0.0020 (8)	−0.0016 (8)
C7	0.0401 (9)	0.0342 (9)	0.0303 (9)	−0.0022 (8)	−0.0027 (7)	−0.0007 (7)
N1	0.0528 (10)	0.0477 (10)	0.0401 (9)	0.0066 (8)	−0.0099 (8)	0.0034 (8)
N2	0.0517 (10)	0.0409 (10)	0.0597 (11)	−0.0054 (8)	−0.0030 (8)	−0.0135 (9)
O1	0.0694 (9)	0.0347 (7)	0.0456 (8)	−0.0054 (6)	−0.0234 (6)	0.0066 (6)
O2	0.0595 (8)	0.0364 (7)	0.0481 (8)	−0.0112 (6)	−0.0187 (6)	0.0030 (6)
O3	0.0768 (11)	0.0651 (10)	0.0682 (11)	−0.0215 (9)	−0.0165 (8)	0.0279 (8)
O4	0.0827 (11)	0.0648 (10)	0.0606 (10)	0.0067 (8)	−0.0370 (8)	0.0070 (8)
O5	0.0684 (10)	0.0626 (10)	0.0878 (13)	−0.0155 (8)	−0.0312 (9)	−0.0163 (9)
O6	0.0879 (12)	0.0435 (9)	0.0802 (12)	−0.0195 (8)	−0.0087 (9)	0.0015 (8)
O7	0.1287 (15)	0.0409 (9)	0.0519 (10)	−0.0040 (10)	−0.0016 (10)	0.0062 (7)
C8	0.0405 (10)	0.0402 (10)	0.0340 (10)	0.0025 (8)	−0.0032 (8)	0.0027 (8)
C9	0.0355 (9)	0.0399 (10)	0.0331 (9)	0.0003 (8)	−0.0011 (7)	−0.0012 (8)
C10	0.0407 (10)	0.0510 (11)	0.0327 (10)	0.0004 (8)	−0.0062 (8)	0.0009 (8)
C11	0.0499 (11)	0.0442 (11)	0.0428 (11)	−0.0006 (9)	−0.0036 (9)	0.0109 (9)
C12	0.0504 (11)	0.0415 (11)	0.0508 (12)	−0.0069 (9)	−0.0012 (9)	0.0013 (9)
N3	0.0418 (9)	0.0454 (9)	0.0379 (9)	−0.0029 (7)	−0.0077 (7)	−0.0034 (7)
N4	0.0662 (11)	0.0430 (9)	0.0487 (10)	−0.0114 (8)	−0.0167 (8)	0.0024 (8)

Geometric parameters (Å, º) top

C1—C2	1.381 (2)	N2—O5	1.222 (2)
C1—C6	1.390 (2)	O7—H7A	0.825 (10)
C1—C7	1.514 (2)	O7—H7B	0.827 (9)
C2—C3	1.375 (2)	C8—N3	1.329 (2)
C2—H2	0.9300	C8—C9	1.385 (2)
C3—C4	1.376 (2)	C8—H8	0.9300
C3—N1	1.468 (2)	C9—N4	1.364 (2)
C4—C5	1.368 (3)	C9—C10	1.389 (2)
C4—H4	0.9300	C10—C11	1.370 (3)
C5—C6	1.378 (2)	C10—H10	0.9300
C5—N2	1.470 (2)	C11—C12	1.365 (3)
C6—H6	0.9300	C11—H11	0.9300
C7—O2	1.2304 (19)	C12—N3	1.330 (2)
C7—O1	1.258 (2)	C12—H12	0.9300
N1—O3	1.214 (2)	N3—H3	0.883 (10)
N1—O4	1.2157 (19)	N4—H4A	0.8600
N2—O6	1.214 (2)	N4—H4B	0.8600

C2—C1—C6	119.60 (16)	O6—N2—C5	118.76 (17)
C2—C1—C7	119.93 (15)	O5—N2—C5	117.47 (18)
C6—C1—C7	120.47 (15)	H7A—O7—H7B	108.3 (15)
C3—C2—C1	119.12 (16)	N3—C8—C9	120.51 (17)
C3—C2—H2	120.4	N3—C8—H8	119.7
C1—C2—H2	120.4	C9—C8—H8	119.7
C2—C3—C4	122.62 (17)	N4—C9—C8	120.26 (16)
C2—C3—N1	118.96 (16)	N4—C9—C10	122.92 (16)
C4—C3—N1	118.41 (16)	C8—C9—C10	116.81 (16)
C5—C4—C3	117.00 (16)	C11—C10—C9	120.80 (17)
C5—C4—H4	121.5	C11—C10—H10	119.6
C3—C4—H4	121.5	C9—C10—H10	119.6
C4—C5—C6	122.68 (16)	C12—C11—C10	119.96 (18)
C4—C5—N2	118.40 (16)	C12—C11—H11	120.0
C6—C5—N2	118.91 (17)	C10—C11—H11	120.0
C5—C6—C1	118.93 (16)	N3—C12—C11	118.68 (18)
C5—C6—H6	120.5	N3—C12—H12	120.7
C1—C6—H6	120.5	C11—C12—H12	120.7
O2—C7—O1	125.55 (16)	C8—N3—C12	123.24 (17)
O2—C7—C1	118.68 (15)	C8—N3—H3	119.5 (14)
O1—C7—C1	115.77 (15)	C12—N3—H3	117.3 (14)
O3—N1—O4	123.39 (17)	C9—N4—H4A	120.0
O3—N1—C3	118.54 (15)	C9—N4—H4B	120.0
O4—N1—C3	118.07 (17)	H4A—N4—H4B	120.0
O6—N2—O5	123.77 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O2	0.83 (1)	1.99 (1)	2.805 (2)	170 (2)
O7—H7B···O1ⁱ	0.83 (1)	2.08 (1)	2.883 (2)	165 (2)
N3—H3···O1	0.88 (1)	1.73 (1)	2.6116 (19)	176 (2)
N4—H4A···O7ⁱⁱ	0.86	2.13	2.904 (2)	149
N4—H4B···O4ⁱⁱⁱ	0.86	2.45	3.223 (2)	150
N4—H4B···O3ⁱⁱ	0.86	2.59	3.110 (2)	120

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) x−1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₅H₇N₂⁺·C₇H₃N₂O₆⁻·H₂O
M_r	324.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.904 (2), 7.0683 (16), 22.331 (5)
β (°)	90.002 (3)
V (Å³)	1405.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.40 × 0.11 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.950, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	7329, 2743, 2110
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.04
No. of reflections	2743
No. of parameters	220
No. of restraints	16
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O2	0.825 (10)	1.990 (10)	2.805 (2)	170 (2)
O7—H7B···O1ⁱ	0.827 (9)	2.075 (10)	2.883 (2)	165 (2)
N3—H3···O1	0.883 (10)	1.730 (10)	2.6116 (19)	176 (2)
N4—H4A···O7ⁱⁱ	0.86	2.13	2.904 (2)	148.9
N4—H4B···O4ⁱⁱⁱ	0.86	2.45	3.223 (2)	150.4
N4—H4B···O3ⁱⁱ	0.86	2.59	3.110 (2)	120.3

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) x−1, −y+1/2, z−1/2.

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