2-Amino-anilinium benzoate.

In the crystal of the title molecular salt, C(6)H(9)N(2) (+)·C(7)H(5)O(2) (-), the cations and anions are linked by N-H⋯O hydrogen bonds, buiding an R(2) (2)(9) ring. Futher N-H⋯O hydrogen bonds generate chains, which develop parallel to the a axis through the formation of R(4) (3)(10) rings..

Related literature

For the properties of amino compounds, see: Fu et al. (2009 ▶); Aminabhavi et al. (1986 ▶); Dai & Fu (2008 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H9N2 +·C7H5O2 −

M = 230.26

Orthorhombic,

a = 6.0211 (12) Å

b = 12.237 (2) Å

c = 16.639 (3) Å

V = 1226.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.15 × 0.10 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.970, T max = 1.000

12656 measured reflections

1638 independent reflections

1133 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.118

S = 1.08

1638 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.16 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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048208/dn2626sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048208/dn2626Isup2.hkl

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

C6H9N2+·C7H5O2−	F(000) = 488
Mr = 230.26	Dx = 1.247 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2805 reflections
a = 6.0211 (12) Å	θ = 3.3–27.5°
b = 12.237 (2) Å	µ = 0.09 mm−1
c = 16.639 (3) Å	T = 298 K
V = 1226.0 (4) Å3	Block, colourless
Z = 4	0.30 × 0.15 × 0.10 mm

Rigaku Mercury2 diffractometer	1638 independent reflections
Radiation source: fine-focus sealed tube	1133 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.3°
CCD profile fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.970, Tmax = 1.000	l = −21→21
12656 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.0477P] where P = (Fo2 + 2Fc2)/3
1638 reflections	(Δ/σ)max = 0.002
155 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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
N1	0.7176 (3)	0.63438 (15)	0.49671 (11)	0.0429 (5)
H1A	0.8339	0.6156	0.5267	0.064*
H1B	0.6171	0.6679	0.5272	0.064*
H1C	0.7617	0.6793	0.4578	0.064*
N2	0.3415 (4)	0.65071 (19)	0.39767 (14)	0.0658 (7)
H2A	0.4535	0.7109	0.3927	0.099*
H2B	0.2137	0.6471	0.3597	0.099*
C1	0.4321 (4)	0.5481 (2)	0.41353 (14)	0.0475 (6)
C2	0.6195 (4)	0.53644 (19)	0.46122 (13)	0.0417 (6)
C3	0.7065 (5)	0.4356 (2)	0.47948 (17)	0.0601 (8)
H3	0.8326	0.4301	0.5115	0.072*
C4	0.6058 (8)	0.3428 (2)	0.4501 (2)	0.0846 (11)
H4	0.6638	0.2743	0.4619	0.101*
C5	0.4195 (8)	0.3522 (3)	0.4032 (2)	0.0845 (10)
H5	0.3511	0.2895	0.3836	0.101*
C6	0.3325 (6)	0.4528 (3)	0.38492 (18)	0.0706 (9)
H6	0.2059	0.4576	0.3531	0.085*
O1	0.8819 (3)	0.79093 (13)	0.39910 (9)	0.0512 (5)
O2	0.5619 (3)	0.87900 (18)	0.39486 (13)	0.0749 (7)
C7	0.7644 (4)	0.8731 (2)	0.38177 (14)	0.0450 (6)
C8	0.8786 (4)	0.9670 (2)	0.34141 (13)	0.0416 (6)
C9	0.7821 (6)	1.0692 (2)	0.33900 (17)	0.0630 (8)
H9	0.6427	1.0799	0.3618	0.076*
C10	0.8903 (8)	1.1555 (3)	0.3032 (2)	0.0858 (11)
H10	0.8253	1.2244	0.3029	0.103*
C11	1.0919 (8)	1.1402 (3)	0.2682 (2)	0.0893 (12)
H11	1.1642	1.1986	0.2438	0.107*
C12	1.1892 (5)	1.0385 (3)	0.26864 (17)	0.0764 (10)
H12	1.3254	1.0278	0.2435	0.092*
C13	1.0847 (4)	0.9529 (2)	0.30625 (14)	0.0535 (7)
H13	1.1531	0.8848	0.3081	0.064*

	U11	U22	U33	U12	U13	U23
N1	0.0360 (10)	0.0443 (11)	0.0485 (11)	0.0012 (10)	−0.0044 (9)	0.0033 (9)
N2	0.0584 (14)	0.0684 (15)	0.0706 (15)	0.0104 (13)	−0.0274 (14)	−0.0004 (12)
C1	0.0447 (14)	0.0537 (16)	0.0441 (13)	−0.0013 (14)	−0.0019 (12)	−0.0034 (12)
C2	0.0403 (13)	0.0442 (13)	0.0405 (12)	−0.0028 (13)	0.0009 (12)	−0.0013 (11)
C3	0.070 (2)	0.0463 (15)	0.0638 (17)	0.0067 (16)	−0.0119 (16)	0.0006 (14)
C4	0.117 (3)	0.0464 (17)	0.090 (2)	0.004 (2)	−0.018 (3)	−0.0056 (16)
C5	0.117 (3)	0.057 (2)	0.080 (2)	−0.022 (2)	−0.015 (2)	−0.0091 (17)
C6	0.073 (2)	0.077 (2)	0.0612 (17)	−0.0195 (18)	−0.0146 (17)	−0.0081 (16)
O1	0.0547 (11)	0.0483 (10)	0.0506 (10)	−0.0027 (9)	0.0006 (10)	0.0044 (8)
O2	0.0383 (10)	0.1060 (17)	0.0804 (14)	−0.0014 (11)	0.0130 (11)	0.0259 (13)
C7	0.0371 (13)	0.0587 (16)	0.0393 (13)	−0.0023 (14)	0.0003 (11)	0.0004 (13)
C8	0.0395 (13)	0.0518 (14)	0.0334 (11)	0.0025 (13)	−0.0023 (11)	0.0032 (11)
C9	0.0675 (19)	0.0622 (18)	0.0592 (16)	0.0089 (17)	−0.0015 (16)	0.0070 (15)
C10	0.125 (3)	0.0573 (18)	0.075 (2)	−0.001 (2)	−0.013 (3)	0.0192 (17)
C11	0.109 (3)	0.095 (3)	0.063 (2)	−0.046 (3)	−0.016 (2)	0.032 (2)
C12	0.058 (2)	0.117 (3)	0.0539 (17)	−0.022 (2)	0.0012 (15)	0.022 (2)
C13	0.0426 (14)	0.0721 (18)	0.0458 (14)	−0.0039 (15)	0.0010 (13)	0.0107 (13)

N1—C2	1.461 (3)	C6—H6	0.9300
N1—H1A	0.8900	O1—C7	1.263 (3)
N1—H1B	0.8900	O2—C7	1.241 (3)
N1—H1C	0.8900	C7—C8	1.499 (3)
N2—C1	1.394 (3)	C8—C9	1.379 (4)
N2—H2A	1.0021	C8—C13	1.383 (4)
N2—H2B	0.9968	C9—C10	1.376 (5)
C1—C2	1.387 (4)	C9—H9	0.9300
C1—C6	1.395 (4)	C10—C11	1.359 (6)
C2—C3	1.375 (3)	C10—H10	0.9300
C3—C4	1.377 (4)	C11—C12	1.375 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.371 (6)	C12—C13	1.373 (4)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.373 (5)	C13—H13	0.9300
C5—H5	0.9300
C2—N1—H1A	109.5	C5—C6—C1	120.7 (3)
C2—N1—H1B	109.5	C5—C6—H6	119.7
H1A—N1—H1B	109.5	C1—C6—H6	119.7
C2—N1—H1C	109.5	O2—C7—O1	123.9 (3)
H1A—N1—H1C	109.5	O2—C7—C8	119.0 (3)
H1B—N1—H1C	109.5	O1—C7—C8	117.1 (2)
C1—N2—H2A	114.5	C9—C8—C13	118.7 (3)
C1—N2—H2B	112.5	C9—C8—C7	121.0 (2)
H2A—N2—H2B	120.0	C13—C8—C7	120.3 (2)
C2—C1—N2	121.3 (2)	C10—C9—C8	120.6 (3)
C2—C1—C6	117.3 (2)	C10—C9—H9	119.7
N2—C1—C6	121.4 (2)	C8—C9—H9	119.7
C3—C2—C1	121.9 (2)	C11—C10—C9	120.2 (3)
C3—C2—N1	119.6 (2)	C11—C10—H10	119.9
C1—C2—N1	118.4 (2)	C9—C10—H10	119.9
C2—C3—C4	119.6 (3)	C10—C11—C12	120.2 (3)
C2—C3—H3	120.2	C10—C11—H11	119.9
C4—C3—H3	120.2	C12—C11—H11	119.9
C5—C4—C3	119.6 (3)	C13—C12—C11	119.9 (3)
C5—C4—H4	120.2	C13—C12—H12	120.1
C3—C4—H4	120.2	C11—C12—H12	120.1
C4—C5—C6	120.9 (3)	C12—C13—C8	120.5 (3)
C4—C5—H5	119.6	C12—C13—H13	119.7
C6—C5—H5	119.6	C8—C13—H13	119.7
N2—C1—C2—C3	177.9 (2)	O1—C7—C8—C9	−163.0 (2)
C6—C1—C2—C3	0.5 (4)	O2—C7—C8—C13	−162.2 (2)
N2—C1—C2—N1	1.7 (4)	O1—C7—C8—C13	16.5 (3)
C6—C1—C2—N1	−175.7 (2)	C13—C8—C9—C10	−0.8 (4)
C1—C2—C3—C4	−0.2 (4)	C7—C8—C9—C10	178.7 (3)
N1—C2—C3—C4	176.0 (3)	C8—C9—C10—C11	1.5 (5)
C2—C3—C4—C5	−0.3 (5)	C9—C10—C11—C12	−0.3 (5)
C3—C4—C5—C6	0.3 (6)	C10—C11—C12—C13	−1.5 (5)
C4—C5—C6—C1	0.1 (5)	C11—C12—C13—C8	2.2 (4)
C2—C1—C6—C5	−0.5 (4)	C9—C8—C13—C12	−1.0 (4)
N2—C1—C6—C5	−177.8 (3)	C7—C8—C13—C12	179.5 (2)
O2—C7—C8—C9	18.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1	0.89	1.83	2.699 (3)	166
N2—H2A···O2	1.00	2.16	3.093 (3)	155
N1—H1B···O1i	0.89	1.94	2.815 (3)	168
N1—H1A···O2ii	0.89	1.90	2.753 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1	0.89	1.83	2.699 (3)	166
N2—H2A⋯O2	1.00	2.16	3.093 (3)	155
N1—H1B⋯O1i	0.89	1.94	2.815 (3)	168
N1—H1A⋯O2ii	0.89	1.90	2.753 (3)	161

Symmetry codes: (i) ; (ii) .