(S)-1-Methoxy-carbonyl-2-(4-nitro-phen-yl)ethanaminium chloride.

The title compound, C(10)H(13)N(2)O(4) (+)·Cl(-), comprises a Cl(-) anion and a protonated aminium cation. The crystal packing is stabilized by cation-anion N-H⋯Cl hydrogen bonds and N-H⋯O hydrogen bonds, building an infinite two-dimensional network parallel to the (001) plane. The S absolute configuration at the chiral center was deduced from the synthetic pathway and confirmed by the X-ray analysis.

Related literature

For details of α-amino acid derivatives as precursors for the synthesis of novel biologically active compounds, see: Lucchese et al. (2007 ▶); Arki et al. (2004 ▶); Hauck et al. (2006 ▶); Dai et al. (2008 ▶); Azim et al. (2006 ▶).

Experimental

Crystal data

C10H13N2O4 +·Cl−

M = 260.67

Monoclinic,

a = 4.825 (3) Å

b = 8.426 (3) Å

c = 15.111 (9) Å

β = 95.64 (4)°

V = 611.4 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 298 (2) K

0.25 × 0.18 × 0.17 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.931, T max = 0.942

6215 measured reflections

2751 independent reflections

2077 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.112

S = 1.03

2751 reflections

154 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1259 Friedel pairs

Flack parameter: −0.03 (9)

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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020874/dn2364sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020874/dn2364Isup2.hkl

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

C10H13N2O4+·Cl–	F000 = 272
Mr = 260.67	Dx = 1.416 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1445 reflections
a = 4.825 (3) Å	θ = 2.4–27.5º
b = 8.426 (3) Å	µ = 0.32 mm−1
c = 15.111 (9) Å	T = 298 (2) K
β = 95.64 (4)º	Block, colourless
V = 611.4 (6) Å3	0.25 × 0.18 × 0.17 mm
Z = 2

Rigaku Mercury2 diffractometer	2751 independent reflections
Radiation source: fine-focus sealed tube	2077 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4º
T = 298(2) K	θmin = 2.7º
ω scans	h = −6→6
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.931, Tmax = 0.942	l = −19→19
6215 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.0855P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.30 e Å−3
2751 reflections	Δρmin = −0.17 e Å−3
154 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1259 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (9)
Secondary atom site location: difference Fourier map

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
Cl1	0.98552 (15)	0.75535 (11)	0.54873 (5)	0.0499 (2)
O3	0.8079 (4)	0.7690 (3)	0.30131 (12)	0.0483 (5)
C9	0.6109 (5)	0.7495 (4)	0.35535 (16)	0.0362 (6)
O4	0.4684 (5)	0.8525 (3)	0.38126 (14)	0.0498 (6)
C8	0.5762 (6)	0.5766 (3)	0.37686 (18)	0.0353 (6)
H8A	0.7584	0.5243	0.3803	0.042*
N2	0.4629 (6)	0.5646 (3)	0.46458 (15)	0.0448 (6)
H11A	0.5788	0.6120	0.5058	0.067*
H11B	0.4447	0.4629	0.4787	0.067*
H11C	0.2973	0.6119	0.4617	0.067*
C4	0.4967 (6)	0.4821 (4)	0.21766 (19)	0.0400 (7)
C7	0.3780 (7)	0.4943 (4)	0.3058 (2)	0.0439 (7)
H7A	0.3369	0.3885	0.3262	0.053*
H7B	0.2044	0.5530	0.2980	0.053*
C1	0.7171 (8)	0.4557 (4)	0.0577 (2)	0.0493 (8)
C2	0.8081 (8)	0.3560 (5)	0.1245 (2)	0.0576 (9)
H2C	0.9440	0.2805	0.1165	0.069*
C3	0.6962 (7)	0.3682 (4)	0.2046 (2)	0.0512 (8)
H3A	0.7551	0.2991	0.2506	0.061*
C5	0.4107 (7)	0.5812 (4)	0.1485 (2)	0.0530 (9)
H5A	0.2761	0.6576	0.1561	0.064*
C6	0.5198 (8)	0.5697 (5)	0.0674 (2)	0.0612 (10)
H6A	0.4609	0.6375	0.0207	0.073*
N1	0.8330 (9)	0.4439 (5)	−0.0288 (2)	0.0722 (10)
O1	1.0166 (8)	0.3463 (5)	−0.0366 (2)	0.1027 (12)
O2	0.7365 (9)	0.5296 (5)	−0.0890 (2)	0.1057 (12)
C10	0.8487 (10)	0.9318 (4)	0.2717 (3)	0.0691 (11)
H10A	0.9951	0.9340	0.2331	0.104*
H10B	0.8984	0.9983	0.3224	0.104*
H10C	0.6794	0.9702	0.2402	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.0520 (4)	0.0476 (4)	0.0505 (4)	0.0037 (4)	0.0075 (3)	−0.0092 (4)
O3	0.0588 (12)	0.0420 (12)	0.0475 (11)	−0.0084 (12)	0.0217 (10)	0.0009 (12)
C9	0.0410 (14)	0.0359 (14)	0.0315 (12)	−0.0017 (16)	0.0027 (11)	−0.0029 (15)
O4	0.0582 (14)	0.0403 (12)	0.0521 (13)	0.0093 (11)	0.0123 (11)	0.0021 (11)
C8	0.0429 (16)	0.0342 (15)	0.0303 (14)	0.0008 (13)	0.0109 (12)	0.0018 (12)
N2	0.0599 (17)	0.0372 (14)	0.0390 (14)	−0.0001 (13)	0.0135 (12)	0.0005 (12)
C4	0.0466 (17)	0.0353 (15)	0.0389 (16)	−0.0111 (13)	0.0074 (14)	−0.0071 (13)
C7	0.0428 (17)	0.0444 (18)	0.0460 (17)	−0.0076 (14)	0.0114 (14)	−0.0031 (15)
C1	0.058 (2)	0.056 (2)	0.0364 (17)	−0.0125 (17)	0.0129 (15)	−0.0138 (15)
C2	0.060 (2)	0.062 (2)	0.052 (2)	0.0040 (19)	0.0099 (17)	−0.0160 (19)
C3	0.067 (2)	0.0434 (18)	0.0431 (18)	−0.0007 (17)	0.0073 (16)	−0.0024 (15)
C5	0.060 (2)	0.053 (2)	0.0465 (19)	0.0070 (17)	0.0083 (16)	0.0000 (17)
C6	0.078 (3)	0.064 (2)	0.0403 (19)	−0.006 (2)	0.0023 (18)	0.0038 (18)
N1	0.085 (3)	0.089 (3)	0.0451 (19)	−0.023 (2)	0.0180 (17)	−0.021 (2)
O1	0.094 (2)	0.141 (3)	0.078 (2)	0.008 (2)	0.0345 (19)	−0.035 (2)
O2	0.155 (3)	0.121 (3)	0.0465 (16)	−0.005 (3)	0.0353 (19)	0.0011 (19)
C10	0.090 (3)	0.052 (2)	0.068 (2)	−0.011 (2)	0.022 (2)	0.013 (2)

O3—C9	1.323 (3)	C1—C2	1.353 (5)
O3—C10	1.462 (4)	C1—C6	1.371 (5)
C9—O4	1.196 (4)	C1—N1	1.475 (4)
C9—C8	1.506 (4)	C2—C3	1.377 (4)
C8—N2	1.486 (3)	C2—H2C	0.9300
C8—C7	1.532 (4)	C3—H3A	0.9300
C8—H8A	0.9800	C5—C6	1.384 (5)
N2—H11A	0.8900	C5—H5A	0.9300
N2—H11B	0.8900	C6—H6A	0.9300
N2—H11C	0.8900	N1—O2	1.217 (5)
C4—C5	1.370 (4)	N1—O1	1.223 (5)
C4—C3	1.387 (5)	C10—H10A	0.9600
C4—C7	1.505 (4)	C10—H10B	0.9600
C7—H7A	0.9700	C10—H10C	0.9600
C7—H7B	0.9700
C9—O3—C10	115.6 (3)	C2—C1—C6	122.2 (3)
O4—C9—O3	125.7 (3)	C2—C1—N1	119.8 (4)
O4—C9—C8	123.5 (3)	C6—C1—N1	118.0 (4)
O3—C9—C8	110.8 (3)	C1—C2—C3	118.9 (3)
N2—C8—C9	108.4 (2)	C1—C2—H2C	120.6
N2—C8—C7	109.6 (2)	C3—C2—H2C	120.6
C9—C8—C7	111.2 (2)	C2—C3—C4	121.0 (3)
N2—C8—H8A	109.2	C2—C3—H3A	119.5
C9—C8—H8A	109.2	C4—C3—H3A	119.5
C7—C8—H8A	109.2	C4—C5—C6	121.4 (3)
C8—N2—H11A	109.5	C4—C5—H5A	119.3
C8—N2—H11B	109.5	C6—C5—H5A	119.3
H11A—N2—H11B	109.5	C1—C6—C5	118.2 (3)
C8—N2—H11C	109.5	C1—C6—H6A	120.9
H11A—N2—H11C	109.5	C5—C6—H6A	120.9
H11B—N2—H11C	109.5	O2—N1—O1	123.7 (4)
C5—C4—C3	118.4 (3)	O2—N1—C1	118.1 (4)
C5—C4—C7	121.4 (3)	O1—N1—C1	118.2 (4)
C3—C4—C7	120.2 (3)	O3—C10—H10A	109.5
C4—C7—C8	112.7 (3)	O3—C10—H10B	109.5
C4—C7—H7A	109.1	H10A—C10—H10B	109.5
C8—C7—H7A	109.1	O3—C10—H10C	109.5
C4—C7—H7B	109.1	H10A—C10—H10C	109.5
C8—C7—H7B	109.1	H10B—C10—H10C	109.5
H7A—C7—H7B	107.8
C10—O3—C9—O4	−0.3 (4)	C1—C2—C3—C4	−1.1 (5)
C10—O3—C9—C8	176.6 (3)	C5—C4—C3—C2	0.9 (5)
O4—C9—C8—N2	−29.2 (4)	C7—C4—C3—C2	−179.7 (3)
O3—C9—C8—N2	153.9 (2)	C3—C4—C5—C6	−0.4 (5)
O4—C9—C8—C7	91.4 (3)	C7—C4—C5—C6	−179.9 (3)
O3—C9—C8—C7	−85.5 (3)	C2—C1—C6—C5	−0.4 (6)
C5—C4—C7—C8	−103.2 (4)	N1—C1—C6—C5	−180.0 (3)
C3—C4—C7—C8	77.3 (4)	C4—C5—C6—C1	0.2 (5)
N2—C8—C7—C4	−172.3 (2)	C2—C1—N1—O2	176.2 (4)
C9—C8—C7—C4	67.8 (3)	C6—C1—N1—O2	−4.2 (5)
C6—C1—C2—C3	0.8 (6)	C2—C1—N1—O1	−2.3 (5)
N1—C1—C2—C3	−179.6 (3)	C6—C1—N1—O1	177.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H11B···O4i	0.89	2.31	2.929 (4)	127
N2—H11B···Cl1i	0.89	2.71	3.380 (3)	133
N2—H11C···Cl1ii	0.89	2.42	3.175 (3)	143
N2—H11A···Cl1	0.89	2.34	3.151 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H11B⋯O4i	0.89	2.31	2.929 (4)	127
N2—H11B⋯Cl1i	0.89	2.71	3.380 (3)	133
N2—H11C⋯Cl1ii	0.89	2.42	3.175 (3)	143
N2—H11A⋯Cl1	0.89	2.34	3.151 (3)	151

Symmetry codes: (i) ; (ii) .