2-Amino-anilinium 2-chloro-acetate.

In the crystal structure of the title compound, C(6)H(9)N(2) (+)·ClCH(2)COO(-), prepared by the reaction of OPDA (orthophenelynediamine) with chloro-acetic -acid, N-H⋯O hydrogen bonds generate ladder-like chains and very weak inter-molecular C-H⋯Cl hydrogen-bonding inter-actions between the anions and cations lead to a supra-molecular network. C-H⋯O inter-actions also occur.

Related literature

For hydrogen bonding with chlorine, see: Brammer et al. (2008 ▶); Metrangolo et al. (2006 ▶, 2009 ▶). For ladder-like networks, see: Kinbara, Hashimoto et al. (1996 ▶); Kinbara, Kai et al. (1996 ▶).

Experimental

Crystal data

C6H9N2 +·C2H2ClO2 −

M = 202.64

Monoclinic,

a = 11.371 (3) Å

b = 4.4852 (11) Å

c = 20.115 (4) Å

β = 110.439 (12)°

V = 961.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 298 K

0.36 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.879, T max = 0.944

9366 measured reflections

1922 independent reflections

1651 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.09

1922 reflections

126 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024554/ds2035sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024554/ds2035Isup2.hkl

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

C6H9N2+·C2H2ClO2−	F(000) = 424
Mr = 202.64	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5050 reflections
a = 11.371 (3) Å	θ = 2.3–26.1°
b = 4.4852 (11) Å	µ = 0.37 mm−1
c = 20.115 (4) Å	T = 298 K
β = 110.439 (12)°	Needle, colorless
V = 961.3 (4) Å3	0.36 × 0.20 × 0.16 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1922 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
graphite	Rint = 0.025
phi and ω scans	θmax = 26.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −14→14
Tmin = 0.879, Tmax = 0.944	k = −5→5
9366 measured reflections	l = −24→24

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.3616P] where P = (Fo2 + 2Fc2)/3
1922 reflections	(Δ/σ)max = 0.001
126 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.29 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
N1	0.38338 (15)	0.3513 (3)	0.89834 (8)	0.0425 (4)
H1A	0.4696	0.3585	0.9056	0.051*
H1B	0.3687	0.1914	0.9249	0.051*
H1C	0.3625	0.5114	0.9189	0.051*
N2	0.4570 (2)	−0.0303 (6)	0.80725 (13)	0.0819 (7)
H2A	0.4758	−0.1428	0.7809	0.098*
H2B	0.5201	0.0394	0.8428	0.098*
C1	0.1923 (2)	0.4640 (5)	0.79778 (11)	0.0539 (5)
H1	0.1695	0.5954	0.8269	0.065*
C2	0.1128 (2)	0.4187 (6)	0.72902 (12)	0.0641 (6)
H2	0.0360	0.5167	0.7117	0.077*
C3	0.1485 (3)	0.2267 (6)	0.68631 (12)	0.0655 (7)
H3	0.0950	0.1932	0.6400	0.079*
C4	0.2628 (2)	0.0833 (6)	0.71141 (12)	0.0630 (6)
H4	0.2861	−0.0422	0.6813	0.076*
C5	0.3443 (2)	0.1229 (5)	0.78112 (11)	0.0499 (5)
C6	0.30556 (18)	0.3157 (4)	0.82373 (10)	0.0422 (4)
Cl1	0.88856 (6)	−0.20415 (18)	1.05309 (4)	0.0787 (3)
O1	0.63853 (15)	0.3221 (4)	0.92605 (9)	0.0630 (5)
O2	0.65904 (16)	0.1467 (3)	1.03239 (8)	0.0563 (4)
C7	0.69161 (19)	0.1690 (4)	0.97966 (10)	0.0453 (5)
C8	0.8017 (2)	−0.0074 (7)	0.97533 (13)	0.0612 (6)
H8A	0.855 (3)	0.122 (8)	0.9661 (16)	0.090 (10)*
H8B	0.767 (3)	−0.161 (9)	0.938 (2)	0.118 (13)*

	U11	U22	U33	U12	U13	U23
N1	0.0520 (9)	0.0381 (8)	0.0424 (8)	−0.0007 (7)	0.0229 (7)	−0.0024 (6)
N2	0.0660 (13)	0.0873 (16)	0.0926 (16)	0.0075 (12)	0.0278 (12)	−0.0425 (13)
C1	0.0615 (13)	0.0508 (12)	0.0534 (12)	0.0014 (10)	0.0250 (10)	0.0040 (9)
C2	0.0615 (13)	0.0702 (15)	0.0563 (13)	0.0000 (12)	0.0150 (11)	0.0151 (12)
C3	0.0715 (15)	0.0782 (16)	0.0434 (12)	−0.0223 (13)	0.0160 (11)	0.0026 (11)
C4	0.0819 (17)	0.0650 (14)	0.0515 (12)	−0.0217 (13)	0.0351 (12)	−0.0159 (11)
C5	0.0571 (12)	0.0476 (11)	0.0528 (11)	−0.0117 (9)	0.0290 (10)	−0.0088 (9)
C6	0.0515 (11)	0.0379 (9)	0.0421 (10)	−0.0073 (8)	0.0228 (8)	0.0004 (7)
Cl1	0.0550 (4)	0.0965 (6)	0.0777 (5)	0.0095 (3)	0.0146 (3)	0.0200 (4)
O1	0.0545 (9)	0.0749 (11)	0.0602 (10)	0.0028 (8)	0.0207 (8)	0.0171 (8)
O2	0.0803 (10)	0.0421 (8)	0.0640 (9)	−0.0001 (7)	0.0472 (8)	−0.0018 (6)
C7	0.0480 (11)	0.0445 (10)	0.0471 (11)	−0.0094 (8)	0.0214 (9)	−0.0046 (8)
C8	0.0584 (13)	0.0771 (17)	0.0549 (13)	0.0100 (12)	0.0285 (11)	0.0064 (12)

N1—C6	1.461 (2)	C3—C4	1.378 (4)
N1—H1A	0.9402	C3—H3	0.9300
N1—H1B	0.9425	C4—C5	1.396 (3)
N1—H1C	0.9015	C4—H4	0.9300
N2—C5	1.385 (3)	C5—C6	1.393 (3)
N2—H2A	0.8138	Cl1—C8	1.767 (3)
N2—H2B	0.8747	O1—C7	1.243 (3)
C1—C2	1.378 (3)	O2—C7	1.244 (2)
C1—C6	1.380 (3)	C7—C8	1.509 (3)
C1—H1	0.9300	C8—H8A	0.90 (3)
C2—C3	1.374 (4)	C8—H8B	0.99 (4)
C2—H2	0.9300
C6—N1—H1A	112.9	C3—C4—C5	121.3 (2)
C6—N1—H1B	109.6	C3—C4—H4	119.4
H1A—N1—H1B	108.6	C5—C4—H4	119.4
C6—N1—H1C	113.4	N2—C5—C6	121.6 (2)
H1A—N1—H1C	109.2	N2—C5—C4	121.3 (2)
H1B—N1—H1C	102.6	C6—C5—C4	117.1 (2)
C5—N2—H2A	118.7	C1—C6—C5	121.37 (19)
C5—N2—H2B	121.3	C1—C6—N1	119.11 (17)
H2A—N2—H2B	115.2	C5—C6—N1	119.45 (18)
C2—C1—C6	120.5 (2)	O1—C7—O2	125.8 (2)
C2—C1—H1	119.8	O1—C7—C8	113.63 (18)
C6—C1—H1	119.8	O2—C7—C8	120.5 (2)
C3—C2—C1	119.1 (2)	C7—C8—Cl1	115.41 (16)
C3—C2—H2	120.4	C7—C8—H8A	107 (2)
C1—C2—H2	120.4	Cl1—C8—H8A	107 (2)
C2—C3—C4	120.7 (2)	C7—C8—H8B	107 (2)
C2—C3—H3	119.7	Cl1—C8—H8B	106 (2)
C4—C3—H3	119.7	H8A—C8—H8B	114 (3)
C6—C1—C2—C3	−0.8 (3)	N2—C5—C6—C1	−178.9 (2)
C1—C2—C3—C4	−0.7 (4)	C4—C5—C6—C1	−0.9 (3)
C2—C3—C4—C5	1.5 (4)	N2—C5—C6—N1	−1.8 (3)
C3—C4—C5—N2	177.4 (2)	C4—C5—C6—N1	176.18 (18)
C3—C4—C5—C6	−0.7 (3)	O1—C7—C8—Cl1	174.88 (19)
C2—C1—C6—C5	1.6 (3)	O2—C7—C8—Cl1	−7.3 (3)
C2—C1—C6—N1	−175.42 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2i	0.90	1.88	2.777 (2)	173
N1—H1B···O2ii	0.94	1.82	2.763 (2)	173
N2—H2B···O1	0.87	2.16	3.004 (3)	163
C4—H4···O1iii	0.93	2.66	3.527 (3)	156
C3—H3···Cl1iv	0.93	3.24	3.985 (3)	138
N2—H2A···N2iii	0.81	2.77	3.587 (4)	179
C8—H8A···Cl1v	0.90 (3)	3.10 (3)	3.878 (3)	146 (3)
C8—H8B···O1vi	0.99 (4)	2.71 (4)	3.491 (4)	136 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O2i	0.90	1.88	2.777 (2)	173
N1—H1B⋯O2ii	0.94	1.82	2.763 (2)	173
N2—H2B⋯O1	0.87	2.16	3.004 (3)	163
C4—H4⋯O1iii	0.93	2.66	3.527 (3)	156
C3—H3⋯Cl1iv	0.93	3.24	3.985 (3)	138
N2—H2A⋯N2iii	0.81	2.77	3.587 (4)	179
C8—H8A⋯Cl1v	0.90 (3)	3.10 (3)	3.878 (3)	146 (3)
C8—H8B⋯O1vi	0.99 (4)	2.71 (4)	3.491 (4)	136 (3)

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