2-Carb-oxy-1-(3-nitro-phen-yl)ethanaminium perchlorate.

In the cation of the title compound, C(9)H(11)N(2)O(4) (+)·ClO(4) (-), the conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal packing, centrosymmetrically related cations inter-act through inter-molecular O-H⋯O hydrogen bonds involving the carb-oxy groups, forming dimers. The dimers and the perchlorate anions are further linked into layers parallel to the ab plane by C-H⋯O and N-H⋯O hydrogen-bonding inter-actions.

Related literature

For the synthesis of β-amino acids, see: Cohen et al. (2002 ▶); Qu et al. (2004 ▶); Zhao (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C9H11N2O4 +·ClO4 −

M = 310.65

Triclinic,

a = 7.5932 (8) Å

b = 7.8843 (1) Å

c = 11.8615 (6) Å

α = 94.745 (3)°

β = 99.780 (7)°

γ = 116.323 (4)°

V = 617.11 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.45 × 0.30 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.884, T max = 0.950

6395 measured reflections

2799 independent reflections

1732 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.237

S = 0.99

2799 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.53 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/S1600536809051319/rz2399sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051319/rz2399Isup2.hkl

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

C9H11N2O4+·ClO4−	Z = 2
Mr = 310.65	F(000) = 320
Triclinic, P1	Dx = 1.672 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5932 (8) Å	Cell parameters from 1641 reflections
b = 7.8843 (1) Å	θ = 3.1–27.5°
c = 11.8615 (6) Å	µ = 0.35 mm−1
α = 94.745 (3)°	T = 293 K
β = 99.780 (7)°	Prism, colourless
γ = 116.323 (4)°	0.45 × 0.30 × 0.15 mm
V = 617.11 (7) Å3

Rigaku SCXmini diffractometer	2799 independent reflections
Radiation source: fine-focus sealed tube	1732 reflections with I > 2σ(I)
graphite	Rint = 0.049
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.9°
CCD Profile fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.884, Tmax = 0.950	l = −15→15
6395 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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.237	w = 1/[σ2(Fo2) + (0.1426P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
2799 reflections	Δρmax = 0.58 e Å−3
183 parameters	Δρmin = −0.53 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (1)

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
Cl1	0.34320 (15)	0.01534 (15)	0.65117 (8)	0.0463 (4)
O5	0.3304 (6)	−0.1381 (5)	0.5737 (3)	0.0772 (11)
O6	0.5400 (5)	0.1058 (5)	0.7279 (3)	0.0763 (11)
O7	0.1979 (6)	−0.0555 (6)	0.7205 (3)	0.0867 (13)
O8	0.3233 (9)	0.1574 (7)	0.5920 (3)	0.0996 (16)
O4	0.1696 (4)	0.4174 (4)	0.4775 (2)	0.0423 (7)
O3	0.0141 (5)	0.5359 (5)	0.3563 (2)	0.0523 (8)
H3	−0.0234	0.5592	0.4138	0.079*
C3	0.7013 (5)	0.4845 (5)	0.1024 (3)	0.0343 (8)
C2	0.6238 (5)	0.4860 (5)	0.1994 (3)	0.0346 (8)
H2	0.6888	0.5908	0.2602	0.042*
C1	0.4454 (5)	0.3264 (5)	0.2039 (3)	0.0315 (7)
N1	0.8866 (5)	0.6592 (5)	0.0985 (3)	0.0467 (9)
N2	0.2618 (5)	0.1458 (5)	0.3442 (3)	0.0444 (8)
H2A	0.2265	0.1591	0.4110	0.067*
H2B	0.3490	0.0984	0.3536	0.067*
H2C	0.1525	0.0659	0.2896	0.067*
C9	0.1278 (5)	0.4556 (5)	0.3827 (3)	0.0345 (8)
C7	0.3587 (5)	0.3383 (5)	0.3081 (3)	0.0338 (8)
H7	0.4696	0.4278	0.3728	0.041*
C6	0.3520 (5)	0.1742 (5)	0.1112 (3)	0.0366 (8)
H6	0.2322	0.0683	0.1136	0.044*
O1	0.9505 (5)	0.6627 (5)	0.0093 (3)	0.0696 (10)
C5	0.4334 (6)	0.1763 (6)	0.0143 (3)	0.0386 (8)
H5	0.3682	0.0730	−0.0475	0.046*
O2	0.9618 (5)	0.7907 (5)	0.1799 (3)	0.0722 (10)
C4	0.6139 (6)	0.3347 (6)	0.0106 (3)	0.0394 (9)
H4	0.6728	0.3382	−0.0524	0.047*
C8	0.2089 (6)	0.4171 (6)	0.2816 (3)	0.0370 (8)
H8A	0.2741	0.5361	0.2528	0.044*
H8B	0.0960	0.3263	0.2198	0.044*

	U11	U22	U33	U12	U13	U23
Cl1	0.0496 (6)	0.0469 (6)	0.0457 (6)	0.0250 (5)	0.0138 (4)	0.0040 (4)
O5	0.077 (3)	0.055 (2)	0.092 (3)	0.0231 (19)	0.034 (2)	−0.0077 (19)
O6	0.054 (2)	0.071 (2)	0.082 (2)	0.0171 (19)	−0.0018 (18)	0.013 (2)
O7	0.062 (2)	0.103 (3)	0.084 (3)	0.023 (2)	0.040 (2)	0.002 (2)
O8	0.185 (5)	0.119 (3)	0.047 (2)	0.119 (4)	0.017 (2)	0.022 (2)
O4	0.0490 (15)	0.0624 (18)	0.0341 (14)	0.0396 (15)	0.0155 (12)	0.0111 (12)
O3	0.0618 (18)	0.086 (2)	0.0394 (14)	0.0580 (18)	0.0179 (14)	0.0155 (15)
C3	0.0284 (17)	0.041 (2)	0.0417 (19)	0.0200 (16)	0.0139 (15)	0.0149 (16)
C2	0.0292 (18)	0.0376 (19)	0.0381 (19)	0.0168 (16)	0.0071 (15)	0.0057 (15)
C1	0.0296 (17)	0.0360 (18)	0.0319 (17)	0.0174 (15)	0.0082 (14)	0.0056 (14)
N1	0.0353 (18)	0.049 (2)	0.065 (2)	0.0217 (17)	0.0210 (17)	0.0245 (19)
N2	0.056 (2)	0.052 (2)	0.0401 (17)	0.0335 (18)	0.0215 (16)	0.0162 (15)
C9	0.0336 (18)	0.0391 (19)	0.0350 (18)	0.0198 (16)	0.0111 (15)	0.0045 (15)
C7	0.0297 (17)	0.0371 (19)	0.0349 (18)	0.0149 (15)	0.0101 (14)	0.0070 (15)
C6	0.0341 (18)	0.0330 (18)	0.0413 (19)	0.0137 (16)	0.0119 (15)	0.0046 (15)
O1	0.062 (2)	0.080 (2)	0.088 (2)	0.0352 (19)	0.053 (2)	0.041 (2)
C5	0.042 (2)	0.040 (2)	0.0376 (19)	0.0215 (18)	0.0115 (16)	0.0028 (16)
O2	0.055 (2)	0.054 (2)	0.074 (2)	−0.0025 (17)	0.0133 (18)	0.0074 (19)
C4	0.043 (2)	0.056 (2)	0.0359 (18)	0.032 (2)	0.0193 (16)	0.0173 (17)
C8	0.043 (2)	0.045 (2)	0.0356 (18)	0.0273 (18)	0.0198 (16)	0.0116 (16)

Cl1—O5	1.414 (3)	N1—O1	1.234 (4)
Cl1—O8	1.419 (4)	N2—C7	1.501 (5)
Cl1—O7	1.429 (4)	N2—H2A	0.8900
Cl1—O6	1.433 (4)	N2—H2B	0.8900
O4—C9	1.214 (4)	N2—H2C	0.8900
O3—C9	1.292 (4)	C9—C8	1.506 (4)
O3—H3	0.8200	C7—C8	1.521 (5)
C3—C4	1.366 (5)	C7—H7	0.9800
C3—C2	1.380 (5)	C6—C5	1.392 (5)
C3—N1	1.481 (5)	C6—H6	0.9300
C2—C1	1.395 (5)	C5—C4	1.397 (5)
C2—H2	0.9300	C5—H5	0.9300
C1—C6	1.384 (5)	C4—H4	0.9300
C1—C7	1.511 (5)	C8—H8A	0.9700
N1—O2	1.207 (5)	C8—H8B	0.9700
O5—Cl1—O8	111.9 (2)	O4—C9—O3	125.3 (3)
O5—Cl1—O7	110.5 (2)	O4—C9—C8	122.8 (3)
O8—Cl1—O7	111.6 (3)	O3—C9—C8	111.9 (3)
O5—Cl1—O6	107.7 (2)	N2—C7—C1	111.0 (3)
O8—Cl1—O6	107.2 (3)	N2—C7—C8	111.1 (3)
O7—Cl1—O6	107.7 (2)	C1—C7—C8	110.1 (3)
C9—O3—H3	109.5	N2—C7—H7	108.2
C4—C3—C2	123.7 (3)	C1—C7—H7	108.2
C4—C3—N1	119.4 (3)	C8—C7—H7	108.2
C2—C3—N1	116.9 (3)	C1—C6—C5	121.4 (3)
C3—C2—C1	118.3 (3)	C1—C6—H6	119.3
C3—C2—H2	120.9	C5—C6—H6	119.3
C1—C2—H2	120.9	C6—C5—C4	119.4 (3)
C6—C1—C2	119.1 (3)	C6—C5—H5	120.3
C6—C1—C7	124.0 (3)	C4—C5—H5	120.3
C2—C1—C7	116.7 (3)	C3—C4—C5	117.9 (3)
O2—N1—O1	124.1 (4)	C3—C4—H4	121.0
O2—N1—C3	118.7 (3)	C5—C4—H4	121.0
O1—N1—C3	117.1 (4)	C9—C8—C7	115.3 (3)
C7—N2—H2A	109.5	C9—C8—H8A	108.4
C7—N2—H2B	109.5	C7—C8—H8A	108.4
H2A—N2—H2B	109.5	C9—C8—H8B	108.4
C7—N2—H2C	109.5	C7—C8—H8B	108.4
H2A—N2—H2C	109.5	H8A—C8—H8B	107.5
H2B—N2—H2C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4	0.89	2.36	2.953 (4)	124
N2—H2A···O8	0.89	2.15	2.884 (5)	139
N2—H2B···O5i	0.89	2.31	3.113 (5)	150
N2—H2B···O6i	0.89	2.34	3.120 (5)	147
N2—H2C···O2ii	0.89	2.15	2.960 (5)	152
O3—H3···O4iii	0.82	1.89	2.690 (4)	167
C2—H2···O8iv	0.93	2.58	3.420 (5)	150
C6—H6···O2ii	0.93	2.54	3.445 (5)	163
C8—H8A···O6iv	0.97	2.50	3.403 (5)	154
C8—H8B···O7v	0.97	2.57	3.134 (6)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4	0.89	2.36	2.953 (4)	124
N2—H2A⋯O8	0.89	2.15	2.884 (5)	139
N2—H2B⋯O5i	0.89	2.31	3.113 (5)	150
N2—H2B⋯O6i	0.89	2.34	3.120 (5)	147
N2—H2C⋯O2ii	0.89	2.15	2.960 (5)	152
O3—H3⋯O4iii	0.82	1.89	2.690 (4)	167
C2—H2⋯O8iv	0.93	2.58	3.420 (5)	150
C6—H6⋯O2ii	0.93	2.54	3.445 (5)	163
C8—H8A⋯O6iv	0.97	2.50	3.403 (5)	154
C8—H8B⋯O7v	0.97	2.57	3.134 (6)	117

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