1-Meth-oxycarbonyl-2-(4-nitro-phen-yl)ethanaminium nitrate.

In the title compound, C(10)H(13)O(4)N(2) (+)·NO(3) (-), the nitro group and the benzene ring are essentially coplanar. The dihedral angle between the benzene ring and the methyl-carboxyl-ate plane is 49.6 (3)°. The crystal structure is stabilized by cation-anion N-H⋯O and N-H⋯N hydrogen bonds, building sheets parallel to (001).

Related literature

For details of α-amino acid derivatives, see: Lucchese et al. (2007 ▶); Arki et al. (2004 ▶); Hauck et al. (2006 ▶); Dai & Fu (2008 ▶); Wen (2008 ▶); Azim et al. (2006 ▶).

Experimental

Crystal data

C10H13N2O4 +·NO3 −

M = 287.23

Monoclinic,

a = 5.3722 (11) Å

b = 8.4244 (17) Å

c = 15.380 (3) Å

β = 93.67 (3)°

V = 694.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 298 (2) K

0.25 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.94, T max = 0.96

7232 measured reflections

1682 independent reflections

1164 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.160

S = 1.04

1682 reflections

181 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.35 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028390/ci2667sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028390/ci2667Isup2.hkl

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

C10H13N2O4+·NO3−	F(000) = 300
Mr = 287.23	Dx = 1.373 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1657 reflections
a = 5.3722 (11) Å	θ = 3.6–27.5°
b = 8.4244 (17) Å	µ = 0.12 mm−1
c = 15.380 (3) Å	T = 298 K
β = 93.67 (3)°	Block, colourless
V = 694.6 (2) Å3	0.25 × 0.20 × 0.20 mm
Z = 2

Rigaku Mercury2 diffractometer	1682 independent reflections
Radiation source: fine-focus sealed tube	1164 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.6°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.94, Tmax = 0.96	l = −19→19
7232 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0812P)2 + 0.1127P] where P = (Fo2 + 2Fc2)/3
1682 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.24 e Å−3
7 restraints	Δρmin = −0.35 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 > 2sigma(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
O6	0.2827 (6)	0.2359 (4)	0.41323 (19)	0.0739 (9)
N2	0.9977 (5)	0.4443 (4)	0.55140 (18)	0.0502 (8)
H2A	0.8876	0.4035	0.5118	0.075*
H2B	1.1460	0.3995	0.5461	0.075*
H2C	1.0094	0.5485	0.5431	0.075*
O4	0.7381 (10)	0.2064 (5)	0.7129 (2)	0.1100 (13)
N3	0.4793 (6)	0.2783 (4)	0.4504 (2)	0.0551 (8)
C8	0.9152 (6)	0.4134 (5)	0.6393 (2)	0.0450 (8)
H8	0.7528	0.4645	0.6444	0.054*
O7	0.6843 (6)	0.2597 (5)	0.4190 (2)	0.0895 (11)
O3	0.9747 (8)	0.1395 (4)	0.6053 (2)	0.0883 (12)
C4	0.9935 (7)	0.4905 (5)	0.7975 (2)	0.0549 (10)
C7	1.1003 (7)	0.4825 (6)	0.7094 (2)	0.0600 (10)
H7A	1.2495	0.4175	0.7135	0.072*
H7B	1.1478	0.5885	0.6921	0.072*
O5	0.4776 (5)	0.3493 (7)	0.5199 (2)	0.0973 (15)
C9	0.8833 (9)	0.2365 (6)	0.6494 (2)	0.0620 (11)
C2	0.9717 (13)	0.4069 (9)	0.9457 (3)	0.0971 (19)
H2	1.0311	0.3444	0.9924	0.117*
C5	0.7944 (10)	0.5923 (6)	0.8092 (3)	0.0721 (13)
H5	0.7337	0.6558	0.7631	0.086*
C3	1.0808 (10)	0.3984 (8)	0.8659 (3)	0.0818 (14)
H3	1.2137	0.3297	0.8593	0.098*
C1	0.7795 (11)	0.5067 (8)	0.9543 (3)	0.0828 (16)
N1	0.6608 (16)	0.5128 (10)	1.0390 (3)	0.120 (2)
C6	0.6851 (10)	0.6006 (7)	0.8881 (3)	0.0839 (15)
H6	0.5514	0.6682	0.8957	0.101*
O2	0.4950 (14)	0.6095 (13)	1.0471 (4)	0.172 (3)
C10	0.6934 (16)	0.0396 (7)	0.7309 (4)	0.1130 (13)
H10A	0.5863	0.0308	0.7784	0.170*
H10B	0.8492	−0.0121	0.7463	0.170*
H10C	0.6150	−0.0099	0.6801	0.170*
O1	0.7474 (15)	0.4254 (10)	1.0972 (3)	0.179 (3)

	U11	U22	U33	U12	U13	U23
O6	0.081 (2)	0.067 (2)	0.0724 (19)	−0.0210 (17)	−0.0044 (16)	−0.0037 (17)
N2	0.0498 (16)	0.0528 (19)	0.0501 (16)	−0.0008 (14)	0.0186 (13)	0.0031 (14)
O4	0.196 (4)	0.0643 (19)	0.0772 (17)	−0.047 (2)	0.069 (2)	−0.0111 (15)
N3	0.0503 (18)	0.057 (2)	0.059 (2)	0.0003 (15)	0.0103 (15)	−0.0039 (17)
C8	0.0437 (17)	0.051 (2)	0.0413 (17)	−0.0039 (16)	0.0150 (14)	−0.0033 (16)
O7	0.074 (2)	0.102 (3)	0.095 (2)	0.019 (2)	0.0339 (18)	−0.010 (2)
O3	0.143 (3)	0.0526 (18)	0.075 (2)	0.0141 (19)	0.044 (2)	0.0034 (17)
C4	0.064 (2)	0.054 (2)	0.0467 (19)	−0.0102 (19)	0.0012 (16)	−0.0040 (18)
C7	0.055 (2)	0.069 (3)	0.056 (2)	−0.006 (2)	0.0083 (17)	0.005 (2)
O5	0.0501 (16)	0.153 (4)	0.089 (2)	0.005 (2)	0.0032 (16)	−0.057 (3)
C9	0.092 (3)	0.053 (2)	0.0432 (18)	−0.004 (2)	0.0229 (19)	−0.0008 (19)
C2	0.138 (5)	0.105 (5)	0.047 (2)	−0.012 (5)	−0.002 (3)	0.009 (3)
C5	0.095 (3)	0.066 (3)	0.054 (2)	0.003 (3)	0.006 (2)	−0.003 (2)
C3	0.095 (3)	0.090 (4)	0.060 (3)	0.007 (3)	−0.001 (2)	0.012 (3)
C1	0.103 (4)	0.094 (4)	0.053 (3)	−0.030 (3)	0.022 (3)	−0.020 (3)
N1	0.166 (6)	0.144 (6)	0.052 (3)	−0.059 (5)	0.028 (3)	−0.027 (4)
C6	0.099 (4)	0.089 (4)	0.066 (3)	0.001 (3)	0.018 (3)	−0.027 (3)
O2	0.183 (6)	0.240 (9)	0.102 (4)	−0.022 (6)	0.070 (4)	−0.058 (5)
C10	0.199 (4)	0.067 (2)	0.0810 (18)	−0.046 (2)	0.067 (2)	−0.0103 (17)
O1	0.265 (8)	0.211 (8)	0.065 (3)	−0.043 (6)	0.046 (4)	0.005 (4)

O6—N3	1.222 (4)	C7—H7A	0.97
N2—C8	1.473 (4)	C7—H7B	0.97
N2—H2A	0.89	C2—C1	1.344 (8)
N2—H2B	0.89	C2—C3	1.396 (7)
N2—H2C	0.89	C2—H2	0.93
O4—C9	1.312 (5)	C5—C6	1.384 (6)
O4—C10	1.455 (7)	C5—H5	0.93
N3—O5	1.225 (5)	C3—H3	0.93
N3—O7	1.241 (4)	C1—C6	1.361 (8)
C8—C9	1.509 (6)	C1—N1	1.488 (7)
C8—C7	1.534 (6)	N1—O2	1.219 (11)
C8—H8	0.98	N1—O1	1.227 (10)
O3—C9	1.189 (5)	C6—H6	0.93
C4—C3	1.366 (6)	C10—H10A	0.96
C4—C5	1.392 (7)	C10—H10B	0.96
C4—C7	1.506 (5)	C10—H10C	0.96
C8—N2—H2A	109.5	O3—C9—C8	124.5 (4)
C8—N2—H2B	109.5	O4—C9—C8	110.1 (4)
H2A—N2—H2B	109.5	C1—C2—C3	119.1 (5)
C8—N2—H2C	109.5	C1—C2—H2	120.4
H2A—N2—H2C	109.5	C3—C2—H2	120.4
H2B—N2—H2C	109.5	C6—C5—C4	121.2 (5)
C9—O4—C10	116.2 (4)	C6—C5—H5	119.4
O6—N3—O5	119.8 (3)	C4—C5—H5	119.4
O6—N3—O7	122.9 (4)	C4—C3—C2	120.4 (5)
O5—N3—O7	117.2 (4)	C4—C3—H3	119.8
N2—C8—C9	108.2 (3)	C2—C3—H3	119.8
N2—C8—C7	111.0 (3)	C2—C1—C6	122.8 (5)
C9—C8—C7	112.0 (4)	C2—C1—N1	118.8 (7)
N2—C8—H8	108.5	C6—C1—N1	118.4 (7)
C9—C8—H8	108.5	O2—N1—O1	124.9 (7)
C7—C8—H8	108.5	O2—N1—C1	118.0 (8)
C3—C4—C5	118.6 (4)	O1—N1—C1	117.0 (9)
C3—C4—C7	122.4 (4)	C1—C6—C5	117.9 (5)
C5—C4—C7	118.9 (4)	C1—C6—H6	121.0
C4—C7—C8	112.4 (3)	C5—C6—H6	121.0
C4—C7—H7A	109.1	O4—C10—H10A	109.5
C8—C7—H7A	109.1	O4—C10—H10B	109.5
C4—C7—H7B	109.1	H10A—C10—H10B	109.5
C8—C7—H7B	109.1	O4—C10—H10C	109.5
H7A—C7—H7B	107.8	H10A—C10—H10C	109.5
O3—C9—O4	125.4 (4)	H10B—C10—H10C	109.5
C3—C4—C7—C8	112.3 (5)	C5—C4—C3—C2	0.0 (8)
C5—C4—C7—C8	−66.0 (5)	C7—C4—C3—C2	−178.3 (5)
N2—C8—C7—C4	165.5 (3)	C1—C2—C3—C4	0.1 (9)
C9—C8—C7—C4	−73.4 (5)	C3—C2—C1—C6	0.1 (9)
C10—O4—C9—O3	1.7 (9)	C3—C2—C1—N1	178.8 (5)
C10—O4—C9—C8	−179.2 (6)	C2—C1—N1—O2	176.4 (7)
N2—C8—C9—O3	19.3 (6)	C6—C1—N1—O2	−4.9 (9)
C7—C8—C9—O3	−103.4 (5)	C2—C1—N1—O1	0.3 (8)
N2—C8—C9—O4	−159.9 (4)	C6—C1—N1—O1	179.1 (6)
C7—C8—C9—O4	77.5 (5)	C2—C1—C6—C5	−0.3 (8)
C3—C4—C5—C6	−0.2 (7)	N1—C1—C6—C5	−179.0 (5)
C7—C4—C5—C6	178.2 (4)	C4—C5—C6—C1	0.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O5i	0.89	1.90	2.771 (4)	166
N2—H2B···N3i	0.89	2.60	3.402 (4)	151
N2—H2B···O6i	0.89	2.61	3.218 (5)	126
N2—H2C···O6ii	0.89	2.35	2.950 (5)	124
N2—H2C···O3iii	0.89	2.41	2.929 (5)	117
N2—H2C···O7iii	0.89	2.47	3.176 (5)	137
N2—H2A···O7	0.89	2.12	2.993 (5)	166
N2—H2A···O5	0.89	2.26	2.917 (4)	130
N2—H2A···N3	0.89	2.56	3.402 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O5i	0.89	1.90	2.771 (4)	166
N2—H2B⋯N3i	0.89	2.60	3.402 (4)	151
N2—H2B⋯O6i	0.89	2.61	3.218 (5)	126
N2—H2C⋯O6ii	0.89	2.35	2.950 (5)	124
N2—H2C⋯O3iii	0.89	2.41	2.929 (5)	117
N2—H2C⋯O7iii	0.89	2.47	3.176 (5)	137
N2—H2A⋯O7	0.89	2.12	2.993 (5)	166
N2—H2A⋯O5	0.89	2.26	2.917 (4)	130
N2—H2A⋯N3	0.89	2.56	3.402 (4)	158

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