3,5-Dicarboxyanilinium nitrate dihydrate.

In the crystal of the title compound, C(8)H(8)NO(4) (+)·NO(3) (-)·2H(2)O, the 5-ammonio-isophthalic acid cations, the nitrate anions and the water mol-ecules are linked by N-H⋯O, O-H⋯O and C-H ⋯O hydrogen bonds into a three-dimensional network. The structure is further stabilized by aromatic π-π stacking inter-actions, with centroid-centroid separations of 3.827 (2) Å.

Related literature

For the crystal structure of 5-amino­isophthalic acid hemihydrate, see: Dobson et al. (1998 ▶). For the use of 5-amino­isophthalic acid as a ligand, see: Liao et al. (2004 ▶).

Experimental

Crystal data

C8H8NO4 +·NO3 −·2H2O

M = 280.20

Monoclinic,

a = 8.3436 (17) Å

b = 8.6234 (17) Å

c = 16.862 (3) Å

β = 97.31 (3)°

V = 1203.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.35 × 0.25 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.960, T max = 0.986

12169 measured reflections

2753 independent reflections

1905 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.129

S = 1.07

2753 reflections

190 parameters

?

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005362/rz2414sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005362/rz2414Isup2.hkl

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

C8H8NO4+·NO3−·2H2O	F(000) = 584
Mr = 280.20	Dx = 1.547 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1753 reflections
a = 8.3436 (17) Å	θ = 3.1–27.5°
b = 8.6234 (17) Å	µ = 0.14 mm−1
c = 16.862 (3) Å	T = 293 K
β = 97.31 (3)°	Prism, colourless
V = 1203.4 (4) Å3	0.35 × 0.25 × 0.10 mm
Z = 4

Rigaku SCXmini diffractometer	2753 independent reflections
Radiation source: fine-focus sealed tube	1905 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD profile fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.960, Tmax = 0.986	l = −21→21
12169 measured reflections

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)] = 0.054	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.7735P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.129	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.28 e Å−3
2753 reflections	Δρmin = −0.24 e Å−3
190 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 restraints	Extinction coefficient: 0.0014 (1)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O4	0.4952 (2)	0.14675 (19)	0.42859 (10)	0.0442 (5)
H4	0.5275	0.0603	0.4432	0.066*
N1	0.3108 (2)	0.6452 (2)	0.29415 (11)	0.0328 (5)
H1A	0.3651	0.5813	0.2658	0.049*
H1B	0.3632	0.7350	0.3010	0.049*
H1C	0.2126	0.6614	0.2682	0.049*
C2	0.3575 (3)	0.4279 (2)	0.38793 (13)	0.0280 (5)
H2	0.4070	0.3744	0.3498	0.034*
O1	0.1136 (3)	0.6025 (2)	0.62566 (11)	0.0545 (6)
H1	0.0669	0.6559	0.6558	0.082*
O3	0.3885 (3)	0.1368 (2)	0.54276 (11)	0.0513 (5)
C4	0.2667 (3)	0.4405 (2)	0.51780 (13)	0.0296 (5)
H4A	0.2556	0.3946	0.5667	0.036*
C1	0.2969 (3)	0.5756 (2)	0.37216 (13)	0.0264 (5)
C5	0.2069 (3)	0.5891 (3)	0.50071 (14)	0.0299 (5)
C6	0.2225 (3)	0.6570 (2)	0.42699 (13)	0.0300 (5)
H6	0.1830	0.7563	0.4152	0.036*
O2	0.0772 (3)	0.8101 (2)	0.54705 (12)	0.0605 (6)
C3	0.3432 (3)	0.3610 (2)	0.46132 (13)	0.0275 (5)
C7	0.1260 (3)	0.6799 (3)	0.55994 (14)	0.0356 (6)
O5	0.2218 (2)	−0.0029 (2)	0.30373 (12)	0.0461 (5)
O6	0.4607 (2)	−0.06093 (19)	0.27628 (11)	0.0441 (5)
O7	0.3495 (2)	0.15470 (19)	0.23390 (12)	0.0460 (5)
N2	0.3433 (2)	0.0312 (2)	0.27105 (12)	0.0333 (5)
C8	0.4106 (3)	0.2034 (3)	0.47971 (13)	0.0304 (5)
O9	0.9920 (2)	0.7569 (2)	0.73715 (12)	0.0422 (5)
O8	0.8512 (3)	0.5594 (3)	0.84014 (16)	0.0667 (7)
H9A	0.916 (5)	0.828 (5)	0.729 (2)	0.091 (13)*
H8A	0.904 (4)	0.500 (5)	0.885 (2)	0.089 (13)*
H8B	0.781 (6)	0.612 (5)	0.861 (3)	0.111 (16)*
H9B	0.949 (6)	0.706 (6)	0.771 (3)	0.14 (2)*

	U11	U22	U33	U12	U13	U23
O4	0.0653 (12)	0.0295 (9)	0.0394 (10)	0.0196 (9)	0.0133 (9)	0.0042 (7)
N1	0.0348 (11)	0.0289 (10)	0.0359 (11)	0.0043 (8)	0.0092 (9)	0.0069 (8)
C2	0.0321 (12)	0.0225 (11)	0.0299 (12)	0.0021 (9)	0.0057 (10)	−0.0010 (9)
O1	0.0824 (15)	0.0496 (11)	0.0354 (10)	0.0243 (10)	0.0225 (10)	0.0014 (9)
O3	0.0760 (14)	0.0357 (10)	0.0470 (11)	0.0214 (10)	0.0261 (10)	0.0177 (8)
C4	0.0365 (13)	0.0251 (11)	0.0269 (12)	0.0028 (9)	0.0025 (10)	0.0010 (9)
C1	0.0283 (11)	0.0236 (11)	0.0275 (11)	−0.0002 (9)	0.0038 (9)	0.0026 (9)
C5	0.0323 (12)	0.0258 (11)	0.0313 (12)	0.0017 (9)	0.0029 (10)	−0.0025 (9)
C6	0.0345 (12)	0.0204 (10)	0.0348 (12)	0.0054 (9)	0.0027 (10)	0.0003 (9)
O2	0.0920 (16)	0.0371 (11)	0.0573 (13)	0.0270 (11)	0.0282 (12)	0.0011 (9)
C3	0.0317 (12)	0.0209 (10)	0.0293 (12)	0.0016 (9)	0.0021 (9)	0.0008 (9)
C7	0.0421 (14)	0.0308 (13)	0.0343 (13)	0.0059 (11)	0.0063 (11)	−0.0055 (10)
O5	0.0385 (10)	0.0427 (10)	0.0604 (12)	−0.0026 (8)	0.0199 (9)	0.0066 (9)
O6	0.0436 (10)	0.0346 (9)	0.0562 (12)	0.0130 (8)	0.0149 (9)	0.0030 (8)
O7	0.0483 (11)	0.0269 (9)	0.0643 (12)	−0.0019 (8)	0.0128 (9)	0.0126 (8)
N2	0.0363 (11)	0.0263 (10)	0.0377 (11)	−0.0009 (9)	0.0063 (9)	−0.0016 (8)
C8	0.0379 (13)	0.0246 (11)	0.0290 (12)	0.0042 (10)	0.0049 (10)	−0.0001 (9)
O9	0.0356 (10)	0.0465 (11)	0.0460 (11)	0.0073 (9)	0.0106 (9)	−0.0011 (9)
O8	0.0748 (16)	0.0582 (14)	0.0742 (17)	0.0179 (12)	0.0371 (14)	0.0138 (12)

O4—C8	1.279 (3)	C4—H4A	0.9300
O4—H4	0.8200	C1—C6	1.371 (3)
N1—C1	1.464 (3)	C5—C6	1.395 (3)
N1—H1A	0.8900	C5—C7	1.496 (3)
N1—H1B	0.8900	C6—H6	0.9300
N1—H1C	0.8900	O2—C7	1.205 (3)
C2—C1	1.383 (3)	C3—C8	1.488 (3)
C2—C3	1.384 (3)	O5—N2	1.249 (2)
C2—H2	0.9300	O6—N2	1.256 (2)
O1—C7	1.309 (3)	O7—N2	1.240 (2)
O1—H1	0.8200	O9—H9A	0.88 (4)
O3—C8	1.243 (3)	O9—H9B	0.84 (5)
C4—C5	1.392 (3)	O8—H8A	0.97 (4)
C4—C3	1.393 (3)	O8—H8B	0.85 (5)
C8—O4—H4	109.5	C6—C5—C7	118.5 (2)
C1—N1—H1A	109.5	C1—C6—C5	119.2 (2)
C1—N1—H1B	109.5	C1—C6—H6	120.4
H1A—N1—H1B	109.5	C5—C6—H6	120.4
C1—N1—H1C	109.5	C2—C3—C4	120.3 (2)
H1A—N1—H1C	109.5	C2—C3—C8	119.59 (19)
H1B—N1—H1C	109.5	C4—C3—C8	120.1 (2)
C1—C2—C3	119.0 (2)	O2—C7—O1	124.5 (2)
C1—C2—H2	120.5	O2—C7—C5	122.6 (2)
C3—C2—H2	120.5	O1—C7—C5	112.9 (2)
C7—O1—H1	109.5	O7—N2—O5	120.9 (2)
C5—C4—C3	119.7 (2)	O7—N2—O6	119.8 (2)
C5—C4—H4A	120.2	O5—N2—O6	119.32 (19)
C3—C4—H4A	120.2	O3—C8—O4	123.7 (2)
C6—C1—C2	121.8 (2)	O3—C8—C3	120.5 (2)
C6—C1—N1	119.39 (19)	O4—C8—C3	115.8 (2)
C2—C1—N1	118.78 (19)	H9A—O9—H9B	96 (4)
C4—C5—C6	119.9 (2)	H8A—O8—H8B	103 (4)
C4—C5—C7	121.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6i	0.93	2.58	3.324 (3)	138
O9—H9A···O7ii	0.88 (4)	2.39 (4)	3.048 (3)	133 (3)
O9—H9A···O5ii	0.88 (4)	1.94 (4)	2.801 (3)	168 (4)
O8—H8B···O3iii	0.85 (5)	2.29 (5)	3.057 (3)	149 (4)
O8—H8A···O2iv	0.97 (4)	2.00 (4)	2.882 (3)	151 (3)
O4—H4···O3v	0.82	1.84	2.652 (2)	169
N1—H1C···O9vi	0.89	1.98	2.839 (3)	163
N1—H1B···O6vii	0.89	2.00	2.859 (3)	161
N1—H1B···O5vii	0.89	2.55	3.134 (3)	124
O9—H9B···O8	0.84 (5)	1.96 (5)	2.796 (3)	171 (5)
N1—H1A···O7i	0.89	2.46	2.933 (3)	114
N1—H1A···O6i	0.89	2.09	2.963 (3)	165
O1—H1···O9viii	0.82	1.80	2.611 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6i	0.93	2.58	3.324 (3)	138
O9—H9A⋯O7ii	0.88 (4)	2.39 (4)	3.048 (3)	133 (3)
O9—H9A⋯O5ii	0.88 (4)	1.94 (4)	2.801 (3)	168 (4)
O8—H8B⋯O3iii	0.85 (5)	2.29 (5)	3.057 (3)	149 (4)
O8—H8A⋯O2iv	0.97 (4)	2.00 (4)	2.882 (3)	151 (3)
O4—H4⋯O3v	0.82	1.84	2.652 (2)	169
N1—H1C⋯O9vi	0.89	1.98	2.839 (3)	163
N1—H1B⋯O6vii	0.89	2.00	2.859 (3)	161
N1—H1B⋯O5vii	0.89	2.55	3.134 (3)	124
O9—H9B⋯O8	0.84 (5)	1.96 (5)	2.796 (3)	171 (5)
N1—H1A⋯O7i	0.89	2.46	2.933 (3)	114
N1—H1A⋯O6i	0.89	2.09	2.963 (3)	165
O1—H1⋯O9viii	0.82	1.80	2.611 (3)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .