Anilinium-3-carboxyl-ate 3-carb-oxy-anilinium nitrate.

The title compound, C7H8NO2(+)·NO3(-)·C7H7NO2, exists in the form of a protonated dimer of two anilinium-3-carboxyl-ate mol-ecules related by an inversion center, and a nitrate anion located on a twofold rotation axis. The bridging H atom occupies, with equal probability, the two sites associated with the carboxyl atoms. In addition to the strong O-H⋯O hydrogen bond, in the crystal, the various units are linked via N-H⋯O and C-H⋯O hydrogen bonds forming a three-dimensional structure.

Related literature

For applications of amino­benzoic acids, see: Congiu et al. (2005 ▶); Swislocka et al. (2005 ▶). For related structures and details of their hydrogen-bonding motifs, see: Arora et al. (1973 ▶); Bahadur et al. (2007 ▶); Hansen et al. (2007 ▶); Lai & Marsh (1967 ▶); Lu et al. (2001 ▶); Smith et al. (1995 ▶); Zaidi et al. (2008 ▶).

Experimental

Crystal data

C7H8NO2 +·NO3 −·C7H7NO2

M = 337.29

Monoclinic,

a = 16.0451 (3) Å

b = 4.7575 (1) Å

c = 19.7143 (4) Å

β = 107.660 (1)°

V = 1433.96 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.23 × 0.16 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.525, T max = 0.806

6955 measured reflections

1777 independent reflections

1604 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.07

1777 reflections

127 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049392/kj2215sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049392/kj2215Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049392/kj2215Isup3.cml

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

C7H8NO2+·NO3−·C7H7NO2	F(000) = 704
Mr = 337.29	Dx = 1.562 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1777 reflections
a = 16.0451 (3) Å	θ = 2.9–28.3°
b = 4.7575 (1) Å	µ = 0.13 mm−1
c = 19.7143 (4) Å	T = 296 K
β = 107.660 (1)°	Plate, pale orange
V = 1433.96 (5) Å3	0.23 × 0.16 × 0.07 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	1777 independent reflections
Radiation source: fine-focus sealed tube	1604 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 28.3°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→21
Tmin = 0.525, Tmax = 0.806	k = −6→6
6955 measured reflections	l = −26→24

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0497P)2 + 1.028P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1777 reflections	Δρmax = 0.29 e Å−3
127 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (11)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
O1	0.03166 (6)	0.8054 (2)	0.04202 (5)	0.0316 (3)
O2	0.11051 (6)	0.75160 (18)	−0.03226 (4)	0.0292 (3)
N1	0.38230 (6)	0.2414 (2)	0.11339 (6)	0.0256 (3)
C1	0.09454 (7)	0.6963 (2)	0.02418 (6)	0.0232 (3)
C2	0.15270 (7)	0.4950 (2)	0.07568 (6)	0.0234 (3)
C3	0.23625 (7)	0.4507 (2)	0.07021 (6)	0.0241 (3)
C4	0.29346 (7)	0.2769 (2)	0.11825 (6)	0.0232 (3)
C5	0.26851 (8)	0.1375 (3)	0.17048 (6)	0.0316 (3)
C6	0.18493 (9)	0.1785 (3)	0.17490 (7)	0.0355 (4)
C7	0.12742 (8)	0.3602 (3)	0.12863 (7)	0.0308 (3)
O3	0.44638 (8)	0.7461 (2)	0.20141 (6)	0.0512 (4)
O4	0.50000	0.3567 (3)	0.25000	0.0540 (5)
N2	0.50000	0.6216 (3)	0.25000	0.0283 (4)
H1N	0.3935 (11)	0.384 (4)	0.0864 (9)	0.045 (4)*
H1O	0.014 (2)	0.953 (8)	0.0144 (17)	0.032 (8)*	0.500
H2N	0.3850 (11)	0.075 (4)	0.0881 (9)	0.044 (4)*
H3	0.25330	0.53810	0.03430	0.0290*
H3N	0.4235 (12)	0.243 (3)	0.1589 (10)	0.043 (4)*
H5	0.30730	0.01800	0.20220	0.0380*
H6	0.16720	0.08300	0.20930	0.0430*
H7	0.07210	0.39160	0.13310	0.0370*

	U11	U22	U33	U12	U13	U23
O1	0.0287 (4)	0.0321 (5)	0.0368 (5)	0.0116 (4)	0.0142 (4)	0.0065 (4)
O2	0.0284 (4)	0.0300 (5)	0.0308 (4)	0.0075 (3)	0.0113 (3)	0.0065 (3)
N1	0.0214 (5)	0.0265 (5)	0.0268 (5)	0.0049 (4)	0.0040 (4)	0.0010 (4)
C1	0.0201 (5)	0.0209 (5)	0.0281 (5)	0.0006 (4)	0.0064 (4)	−0.0005 (4)
C2	0.0222 (5)	0.0215 (5)	0.0257 (5)	0.0022 (4)	0.0059 (4)	−0.0005 (4)
C3	0.0232 (5)	0.0232 (5)	0.0254 (5)	0.0021 (4)	0.0068 (4)	0.0023 (4)
C4	0.0214 (5)	0.0223 (5)	0.0247 (5)	0.0023 (4)	0.0050 (4)	−0.0022 (4)
C5	0.0334 (6)	0.0322 (6)	0.0281 (6)	0.0089 (5)	0.0078 (5)	0.0077 (5)
C6	0.0390 (7)	0.0392 (7)	0.0321 (6)	0.0062 (6)	0.0164 (5)	0.0117 (5)
C7	0.0275 (6)	0.0335 (6)	0.0340 (6)	0.0044 (5)	0.0132 (5)	0.0038 (5)
O3	0.0579 (7)	0.0333 (6)	0.0462 (6)	0.0102 (5)	−0.0086 (5)	0.0069 (5)
O4	0.0663 (10)	0.0240 (7)	0.0470 (9)	0.0000	−0.0196 (7)	0.0000
N2	0.0291 (7)	0.0251 (7)	0.0286 (7)	0.0000	0.0056 (6)	0.0000

O1—C1	1.2753 (15)	C2—C3	1.3932 (17)
O2—C1	1.2434 (14)	C2—C7	1.3865 (17)
O1—H1O	0.88 (4)	C3—C4	1.3769 (15)
O3—N2	1.2283 (13)	C4—C5	1.3822 (17)
O4—N2	1.260 (2)	C5—C6	1.384 (2)
N1—C4	1.4671 (16)	C6—C7	1.386 (2)
N1—H2N	0.944 (18)	C3—H3	0.9300
N1—H3N	0.939 (19)	C5—H5	0.9300
N1—H1N	0.913 (18)	C6—H6	0.9300
C1—C2	1.4980 (15)	C7—H7	0.9300
C1—O1—H1O	107 (2)	C2—C3—C4	119.60 (10)
C4—N1—H3N	110.7 (12)	C3—C4—C5	121.15 (11)
H1N—N1—H2N	105.5 (16)	N1—C4—C3	118.84 (10)
C4—N1—H2N	109.4 (11)	N1—C4—C5	120.01 (10)
H2N—N1—H3N	112.3 (14)	C4—C5—C6	118.98 (12)
H1N—N1—H3N	110.2 (15)	C5—C6—C7	120.73 (13)
C4—N1—H1N	108.6 (12)	C2—C7—C6	119.71 (12)
O3i—N2—O4	118.83 (8)	C2—C3—H3	120.00
O3—N2—O4	118.83 (8)	C4—C3—H3	120.00
O3—N2—O3i	122.34 (13)	C6—C5—H5	120.00
O2—C1—C2	119.12 (10)	C4—C5—H5	121.00
O1—C1—C2	117.10 (10)	C5—C6—H6	120.00
O1—C1—O2	123.76 (10)	C7—C6—H6	120.00
C3—C2—C7	119.77 (10)	C2—C7—H7	120.00
C1—C2—C3	117.42 (10)	C6—C7—H7	120.00
C1—C2—C7	122.79 (11)
O1—C1—C2—C3	−158.16 (10)	C3—C2—C7—C6	−1.16 (18)
O1—C1—C2—C7	20.10 (16)	C2—C3—C4—N1	−177.64 (9)
O2—C1—C2—C3	20.63 (15)	C2—C3—C4—C5	2.25 (16)
O2—C1—C2—C7	−161.12 (11)	N1—C4—C5—C6	178.75 (11)
C1—C2—C3—C4	177.24 (9)	C3—C4—C5—C6	−1.13 (18)
C7—C2—C3—C4	−1.08 (16)	C4—C5—C6—C7	−1.2 (2)
C1—C2—C7—C6	−179.38 (11)	C5—C6—C7—C2	2.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1ii	0.88 (4)	1.61 (4)	2.4868 (13)	171 (4)
O1—H1O···O2ii	0.88 (4)	2.55 (3)	3.0686 (14)	118 (3)
N1—H1N···O2iii	0.913 (18)	2.027 (19)	2.9157 (13)	164.2 (17)
N1—H2N···O2iv	0.944 (18)	1.918 (18)	2.8609 (13)	177.0 (16)
N1—H3N···O3v	0.939 (19)	2.498 (15)	2.9220 (14)	107.6 (11)
N1—H3N···O3	0.939 (19)	2.526 (15)	2.9582 (14)	108.3 (11)
N1—H3N···O4	0.939 (19)	1.920 (19)	2.8345 (11)	163.9 (13)
C3—H3···O2iii	0.93	2.41	3.1189 (15)	132
C5—H5···O3v	0.93	2.58	3.3058 (18)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1i	0.88 (4)	1.61 (4)	2.4868 (13)	171 (4)
O1—H1O⋯O2i	0.88 (4)	2.55 (3)	3.0686 (14)	118 (3)
N1—H1N⋯O2ii	0.913 (18)	2.027 (19)	2.9157 (13)	164.2 (17)
N1—H2N⋯O2iii	0.944 (18)	1.918 (18)	2.8609 (13)	177.0 (16)
N1—H3N⋯O3iv	0.939 (19)	2.498 (15)	2.9220 (14)	107.6 (11)
N1—H3N⋯O3	0.939 (19)	2.526 (15)	2.9582 (14)	108.3 (11)
N1—H3N⋯O4	0.939 (19)	1.920 (19)	2.8345 (11)	163.9 (13)
C3—H3⋯O2ii	0.93	2.41	3.1189 (15)	132
C5—H5⋯O3iv	0.93	2.58	3.3058 (18)	135

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