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

In the title compound, C(9)H(11)N(2)O(4) (+)·ClO(4) (-), the organic cations form centrosymmetric dimers via a pair of O-H⋯O hydrogen bonds between the carboxyl groups. In the crystal, N-H⋯O inter-actions between the protonated amine group and the perchlorate anions and the nitro group connect the components into a two-dimensional network parallel to (001).

Related literature

For methods of preparation of β-amino acids, see: Cohen et al. (2002 ▶); Qu et al. (2004 ▶).

Experimental

Crystal data

C9H11N2O4 +·ClO4 −

M = 310.65

Triclinic,

a = 7.4737 (10) Å

b = 7.7676 (8) Å

c = 11.8234 (11) Å

α = 94.973 (5)°

β = 99.093 (4)°

γ = 115.574 (9)°

V = 602.04 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 93 K

0.45 × 0.30 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.882, T max = 0.950

6395 measured reflections

2737 independent reflections

1732 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.08

2737 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.38 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, New_Global_Publ_Block. DOI: 10.1107/S1600536809052167/gk2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052167/gk2243Isup2.hkl

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

C9H11N2O4+·ClO4−	Z = 2
Mr = 310.65	F(000) = 320
Triclinic, P1	Dx = 1.713 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4737 (10) Å	Cell parameters from 1721 reflections
b = 7.7676 (8) Å	θ = 3.1–27.5°
c = 11.8234 (11) Å	µ = 0.36 mm−1
α = 94.973 (5)°	T = 93 K
β = 99.093 (4)°	Prism, colorless
γ = 115.574 (9)°	0.45 × 0.30 × 0.15 mm
V = 602.04 (12) Å3

Rigaku SCXmini diffractometer	2737 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°
ω and φ scan	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.882, 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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.395P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2737 reflections	Δρmax = 0.41 e Å−3
183 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

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
O1	0.03107 (18)	−0.28766 (17)	0.32513 (10)	0.0261 (3)
O2	0.04653 (17)	−0.16514 (17)	0.49951 (10)	0.0222 (2)
O3	0.98215 (17)	−0.04224 (17)	0.14192 (9)	0.0188 (2)
H3	1.0329	−0.0530	0.0868	0.028*
O4	0.82886 (16)	0.08503 (15)	0.02079 (9)	0.0166 (2)
N1	0.11075 (18)	−0.15634 (18)	0.40993 (11)	0.0163 (3)
N2	0.74545 (19)	0.36296 (18)	0.15908 (10)	0.0155 (2)
H2D	0.8712	0.4242	0.2025	0.023*
H2B	0.6791	0.4320	0.1712	0.023*
H2C	0.7504	0.3487	0.0843	0.023*
C1	0.2944 (2)	0.0167 (2)	0.40370 (12)	0.0136 (3)
C2	0.3868 (2)	0.1673 (2)	0.49778 (12)	0.0142 (3)
H2A	0.3309	0.1630	0.5630	0.017*
C3	0.5666 (2)	0.3255 (2)	0.49154 (12)	0.0150 (3)
H3A	0.6328	0.4284	0.5536	0.018*
C4	0.6474 (2)	0.3303 (2)	0.39298 (12)	0.0146 (3)
H4	0.7681	0.4360	0.3899	0.018*
C5	0.5485 (2)	0.1772 (2)	0.29839 (12)	0.0137 (3)
C6	0.3711 (2)	0.0183 (2)	0.30398 (12)	0.0139 (3)
H6	0.3046	−0.0853	0.2423	0.017*
C7	0.6363 (2)	0.1664 (2)	0.19179 (12)	0.0142 (3)
H7	0.5242	0.0828	0.1264	0.017*
C8	0.7776 (2)	0.0740 (2)	0.21606 (12)	0.0146 (3)
H8A	0.8887	0.1565	0.2808	0.018*
H8B	0.7035	−0.0492	0.2399	0.018*
C9	0.8654 (2)	0.0398 (2)	0.11572 (12)	0.0136 (3)
Cl1	0.33694 (5)	0.50865 (5)	0.14980 (3)	0.01593 (11)
O5	0.18796 (17)	0.43639 (18)	0.21983 (10)	0.0261 (3)
O7	0.31799 (18)	0.35386 (17)	0.06549 (11)	0.0270 (3)
O8	0.3095 (2)	0.6550 (2)	0.09212 (10)	0.0302 (3)
O6	0.53816 (16)	0.59598 (16)	0.22457 (10)	0.0209 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0238 (6)	0.0184 (6)	0.0237 (6)	−0.0008 (5)	0.0036 (5)	0.0009 (5)
O2	0.0208 (5)	0.0255 (6)	0.0254 (6)	0.0112 (5)	0.0135 (5)	0.0098 (5)
O3	0.0227 (5)	0.0280 (6)	0.0151 (5)	0.0186 (5)	0.0074 (4)	0.0048 (4)
O4	0.0196 (5)	0.0206 (5)	0.0144 (5)	0.0130 (4)	0.0051 (4)	0.0031 (4)
N1	0.0138 (6)	0.0171 (6)	0.0197 (6)	0.0082 (5)	0.0035 (5)	0.0062 (5)
N2	0.0186 (6)	0.0164 (6)	0.0148 (5)	0.0099 (5)	0.0060 (5)	0.0034 (5)
C1	0.0119 (6)	0.0146 (7)	0.0169 (6)	0.0079 (5)	0.0031 (5)	0.0049 (5)
C2	0.0155 (6)	0.0176 (7)	0.0140 (6)	0.0105 (6)	0.0056 (5)	0.0047 (5)
C3	0.0162 (6)	0.0136 (7)	0.0156 (6)	0.0083 (5)	0.0016 (5)	−0.0001 (5)
C4	0.0121 (6)	0.0124 (6)	0.0193 (7)	0.0050 (5)	0.0045 (5)	0.0032 (5)
C5	0.0153 (6)	0.0153 (7)	0.0145 (6)	0.0098 (5)	0.0054 (5)	0.0032 (5)
C6	0.0148 (6)	0.0140 (6)	0.0145 (6)	0.0086 (5)	0.0017 (5)	0.0012 (5)
C7	0.0144 (6)	0.0135 (6)	0.0146 (6)	0.0061 (5)	0.0047 (5)	0.0007 (5)
C8	0.0167 (6)	0.0153 (6)	0.0148 (6)	0.0084 (5)	0.0073 (5)	0.0039 (5)
C9	0.0122 (6)	0.0119 (6)	0.0157 (6)	0.0045 (5)	0.0041 (5)	0.0010 (5)
Cl1	0.01637 (17)	0.01607 (18)	0.01561 (17)	0.00828 (13)	0.00303 (13)	−0.00028 (13)
O5	0.0183 (5)	0.0306 (6)	0.0253 (6)	0.0070 (5)	0.0087 (5)	−0.0011 (5)
O7	0.0272 (6)	0.0203 (6)	0.0294 (6)	0.0086 (5)	0.0082 (5)	−0.0080 (5)
O8	0.0498 (8)	0.0372 (7)	0.0175 (5)	0.0332 (6)	0.0043 (5)	0.0059 (5)
O6	0.0167 (5)	0.0202 (5)	0.0231 (5)	0.0072 (4)	0.0013 (4)	0.0023 (4)

O1—N1	1.2288 (17)	C3—H3A	0.9300
O2—N1	1.2255 (17)	C4—C5	1.400 (2)
O3—C9	1.3011 (18)	C4—H4	0.9300
O3—H3	0.8200	C5—C6	1.384 (2)
O4—C9	1.2296 (18)	C5—C7	1.5217 (18)
N1—C1	1.4670 (18)	C6—H6	0.9300
N2—C7	1.5075 (18)	C7—C8	1.519 (2)
N2—H2D	0.8900	C7—H7	0.9800
N2—H2B	0.8900	C8—C9	1.5000 (18)
N2—H2C	0.8900	C8—H8A	0.9700
C1—C2	1.384 (2)	C8—H8B	0.9700
C1—C6	1.3889 (19)	Cl1—O7	1.4354 (11)
C2—C3	1.394 (2)	Cl1—O5	1.4396 (12)
C2—H2A	0.9300	Cl1—O8	1.4455 (12)
C3—C4	1.391 (2)	Cl1—O6	1.4486 (11)
C9—O3—H3	109.5	C5—C6—C1	118.60 (13)
O2—N1—O1	123.17 (13)	C5—C6—H6	120.7
O2—N1—C1	118.90 (12)	C1—C6—H6	120.7
O1—N1—C1	117.91 (12)	N2—C7—C8	111.06 (11)
C7—N2—H2D	109.5	N2—C7—C5	111.99 (11)
C7—N2—H2B	109.5	C8—C7—C5	108.58 (11)
H2D—N2—H2B	109.5	N2—C7—H7	108.4
C7—N2—H2C	109.5	C8—C7—H7	108.4
H2D—N2—H2C	109.5	C5—C7—H7	108.4
H2B—N2—H2C	109.5	C9—C8—C7	115.16 (12)
C2—C1—C6	123.03 (13)	C9—C8—H8A	108.5
C2—C1—N1	119.16 (12)	C7—C8—H8A	108.5
C6—C1—N1	117.78 (13)	C9—C8—H8B	108.5
C1—C2—C3	117.80 (13)	C7—C8—H8B	108.5
C1—C2—H2A	121.1	H8A—C8—H8B	107.5
C3—C2—H2A	121.1	O4—C9—O3	125.13 (13)
C4—C3—C2	120.38 (13)	O4—C9—C8	122.98 (13)
C4—C3—H3A	119.8	O3—C9—C8	111.90 (12)
C2—C3—H3A	119.8	O7—Cl1—O5	110.51 (7)
C3—C4—C5	120.49 (13)	O7—Cl1—O8	110.15 (7)
C3—C4—H4	119.8	O5—Cl1—O8	109.25 (8)
C5—C4—H4	119.8	O7—Cl1—O6	109.10 (7)
C6—C5—C4	119.70 (13)	O5—Cl1—O6	109.02 (7)
C6—C5—C7	116.93 (12)	O8—Cl1—O6	108.78 (8)
C4—C5—C7	123.14 (12)
O2—N1—C1—C2	−1.71 (19)	C7—C5—C6—C1	175.40 (12)
O1—N1—C1—C2	179.73 (13)	C2—C1—C6—C5	0.3 (2)
O2—N1—C1—C6	176.20 (12)	N1—C1—C6—C5	−177.56 (12)
O1—N1—C1—C6	−2.37 (19)	C6—C5—C7—N2	148.40 (12)
C6—C1—C2—C3	−0.9 (2)	C4—C5—C7—N2	−37.23 (18)
N1—C1—C2—C3	176.88 (12)	C6—C5—C7—C8	−88.61 (15)
C1—C2—C3—C4	0.5 (2)	C4—C5—C7—C8	85.76 (16)
C2—C3—C4—C5	0.6 (2)	N2—C7—C8—C9	−60.66 (16)
C3—C4—C5—C6	−1.2 (2)	C5—C7—C8—C9	175.79 (12)
C3—C4—C5—C7	−175.45 (13)	C7—C8—C9—O4	0.9 (2)
C4—C5—C6—C1	0.8 (2)	C7—C8—C9—O3	−179.00 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O6i	0.97	2.46	3.3742 (19)	157
C8—H8A···O2ii	0.97	2.56	3.3053 (19)	134
C6—H6···O8i	0.93	2.59	3.4263 (19)	151
C4—H4···O1iii	0.93	2.48	3.3858 (19)	163
O3—H3···O4iv	0.82	1.82	2.6381 (14)	172
N2—H2D···O5v	0.89	2.30	3.0542 (17)	142
N2—H2D···O1iii	0.89	2.26	2.9200 (17)	130
N2—H2C···O8vi	0.89	2.06	2.9159 (17)	162
N2—H2C···O4	0.89	2.45	2.9317 (16)	114
N2—H2B···O7	0.89	2.57	3.1795 (18)	126
N2—H2B···O6	0.89	2.09	2.9720 (17)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4i	0.82	1.82	2.6381 (14)	172
N2—H2D⋯O5ii	0.89	2.30	3.0542 (17)	142
N2—H2D⋯O1iii	0.89	2.26	2.9200 (17)	130
N2—H2C⋯O8iv	0.89	2.06	2.9159 (17)	162
N2—H2C⋯O4	0.89	2.45	2.9317 (16)	114
N2—H2B⋯O7	0.89	2.57	3.1795 (18)	126
N2—H2B⋯O6	0.89	2.09	2.9720 (17)	172

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