(S)-1-Methoxy-carbonyl-3-(4-nitro-phen-yl)propan-2-aminium bromide.

In the crystal structure of the title compound, C(10)H(13)N(2)O(4) (+)·Br(-), inter-molecular N-H⋯Br and N-H⋯(O,Br) hydrogen bonds link the cations and anions into a two-dimensional network parallel to the ab plane.

Related literature

For applications of metal-organic coordination compounds, see: Xiong et al. (1999 ▶); Fu, Zhang et al. (2008 ▶); Fu & Xiong (2008 ▶). For metal-organic frameworks with amino acid deriv­atives, see: Chen et al. (2000 ▶); Xie et al. (2002 ▶); Fu et al. (2007 ▶).

Experimental

Crystal data

C10H13N2O4 +·Br−

M = 305.13

Monoclinic,

a = 4.9323 (10) Å

b = 8.6233 (17) Å

c = 15.226 (3) Å

β = 95.77 (3)°

V = 644.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 3.20 mm−1

T = 298 K

0.40 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.90, T max = 1.00

6658 measured reflections

2917 independent reflections

2532 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.085

S = 1.04

2917 reflections

154 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1202 Friedel pairs

Flack parameter: 0.008 (5)

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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034904/cv2604sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034904/cv2604Isup2.hkl

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

C10H13N2O4+·Br−	F(000) = 308
Mr = 305.13	Dx = 1.573 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2532 reflections
a = 4.9323 (10) Å	θ = 3.6–27.5°
b = 8.6233 (17) Å	µ = 3.20 mm−1
c = 15.226 (3) Å	T = 298 K
β = 95.77 (3)°	Needle, colourless
V = 644.3 (2) Å3	0.40 × 0.05 × 0.05 mm
Z = 2

Rigaku Mercury2 diffractometer	2917 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.6°
CCD profile fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.90, Tmax = 1.00	l = −19→19
6658 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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2)]
S = 1.03	(Δ/σ)max < 0.001
2917 reflections	Δρmax = 0.62 e Å−3
154 parameters	Δρmin = −0.30 e Å−3
1 restraint	Absolute structure: Flack (1983), 1202 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.008 (5)

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
C6	0.4984 (8)	0.4001 (4)	0.7127 (2)	0.0390 (9)
C2	0.8039 (10)	0.2806 (6)	0.6203 (3)	0.0565 (12)
H2	0.9359	0.2063	0.6122	0.068*
C7	0.3794 (8)	0.4113 (5)	0.7995 (2)	0.0438 (10)
H7A	0.3349	0.3081	0.8188	0.053*
H7B	0.2118	0.4708	0.7916	0.053*
C3	0.7186 (9)	0.3798 (6)	0.5544 (3)	0.0527 (12)
C5	0.4128 (9)	0.5000 (5)	0.6421 (3)	0.0554 (11)
H5	0.2796	0.5742	0.6489	0.067*
C4	0.5236 (10)	0.4886 (6)	0.5644 (3)	0.0642 (15)
H4	0.4667	0.5550	0.5180	0.077*
C1	0.6940 (9)	0.2910 (5)	0.6986 (3)	0.0481 (11)
H1	0.7523	0.2226	0.7439	0.058*
O1	0.7970 (5)	0.6832 (4)	0.79876 (16)	0.0488 (7)
C9	0.6074 (6)	0.6629 (6)	0.85319 (19)	0.0360 (7)
O2	0.4710 (6)	0.7600 (3)	0.88109 (18)	0.0495 (7)
C8	0.5764 (8)	0.4886 (4)	0.8712 (2)	0.0325 (8)
H8	0.7551	0.4384	0.8731	0.039*
N2	0.8359 (11)	0.3691 (6)	0.4697 (3)	0.0759 (13)
O3	1.0072 (9)	0.2696 (7)	0.4603 (2)	0.1077 (17)
O4	0.7514 (11)	0.4561 (6)	0.4108 (3)	0.1200 (18)
C10	0.8330 (12)	0.8435 (6)	0.7701 (3)	0.0717 (15)
H10A	0.9736	0.8472	0.7308	0.107*
H10B	0.8837	0.9076	0.8206	0.107*
H10C	0.6653	0.8808	0.7399	0.107*
N1	0.4679 (6)	0.4728 (4)	0.95973 (18)	0.0391 (8)
H1A	0.6015	0.4736	1.0021	0.059*
H1B	0.3245	0.5428	0.9591	0.059*
H1C	0.3835	0.3672	0.9607	0.059*
Br1	0.99538 (6)	0.66497 (4)	0.05395 (2)	0.04632 (13)

	U11	U22	U33	U12	U13	U23
C6	0.045 (2)	0.043 (2)	0.029 (2)	−0.0124 (19)	0.0045 (17)	−0.0031 (18)
C2	0.065 (3)	0.061 (3)	0.045 (3)	0.003 (2)	0.009 (2)	−0.018 (2)
C7	0.042 (2)	0.050 (2)	0.041 (2)	−0.014 (2)	0.0121 (18)	−0.006 (2)
C3	0.064 (3)	0.064 (3)	0.032 (2)	−0.019 (2)	0.015 (2)	−0.014 (2)
C5	0.062 (3)	0.056 (3)	0.049 (3)	0.007 (2)	0.006 (2)	0.002 (2)
C4	0.096 (4)	0.064 (3)	0.033 (3)	−0.005 (3)	0.010 (3)	0.008 (2)
C1	0.063 (3)	0.041 (2)	0.040 (2)	0.003 (2)	0.005 (2)	−0.0061 (19)
O1	0.0659 (16)	0.0393 (17)	0.0455 (14)	−0.0094 (17)	0.0266 (12)	−0.0001 (15)
C9	0.0413 (16)	0.0386 (16)	0.0280 (16)	−0.001 (3)	0.0032 (13)	0.001 (2)
O2	0.0603 (18)	0.0379 (16)	0.0533 (18)	0.0130 (15)	0.0201 (14)	0.0078 (14)
C8	0.039 (2)	0.0319 (19)	0.0278 (19)	0.0033 (17)	0.0099 (15)	−0.0005 (16)
N2	0.098 (4)	0.094 (3)	0.039 (3)	−0.028 (3)	0.024 (3)	−0.021 (2)
O3	0.109 (4)	0.151 (5)	0.070 (3)	−0.003 (3)	0.044 (3)	−0.034 (3)
O4	0.177 (5)	0.142 (4)	0.049 (3)	−0.017 (4)	0.048 (3)	0.001 (3)
C10	0.103 (4)	0.058 (3)	0.059 (3)	−0.015 (3)	0.031 (3)	0.010 (2)
N1	0.054 (2)	0.0350 (17)	0.0299 (17)	0.0033 (15)	0.0137 (15)	0.0039 (14)
Br1	0.0471 (2)	0.0436 (2)	0.0490 (2)	0.0020 (3)	0.00881 (15)	−0.0088 (3)

C6—C1	1.380 (6)	O1—C9	1.322 (4)
C6—C5	1.408 (5)	O1—C10	1.466 (6)
C6—C7	1.503 (5)	C9—O2	1.180 (5)
C2—C3	1.353 (6)	C9—C8	1.538 (6)
C2—C1	1.363 (5)	C8—N1	1.506 (4)
C2—H2	0.9300	C8—H8	0.9800
C7—C8	1.538 (5)	N2—O4	1.210 (6)
C7—H7A	0.9700	N2—O3	1.223 (6)
C7—H7B	0.9700	C10—H10A	0.9600
C3—C4	1.363 (6)	C10—H10B	0.9600
C3—N2	1.468 (6)	C10—H10C	0.9600
C5—C4	1.356 (5)	N1—H1A	0.8742
C5—H5	0.9300	N1—H1B	0.9289
C4—H4	0.9300	N1—H1C	1.0023
C1—H1	0.9300
C1—C6—C5	117.4 (4)	O2—C9—O1	126.6 (5)
C1—C6—C7	121.4 (4)	O2—C9—C8	124.0 (3)
C5—C6—C7	121.2 (4)	O1—C9—C8	109.3 (4)
C3—C2—C1	119.1 (4)	N1—C8—C9	107.4 (3)
C3—C2—H2	120.4	N1—C8—C7	109.9 (3)
C1—C2—H2	120.4	C9—C8—C7	111.4 (3)
C6—C7—C8	112.1 (3)	N1—C8—H8	109.4
C6—C7—H7A	109.2	C9—C8—H8	109.4
C8—C7—H7A	109.2	C7—C8—H8	109.4
C6—C7—H7B	109.2	O4—N2—O3	122.6 (5)
C8—C7—H7B	109.2	O4—N2—C3	118.3 (6)
H7A—C7—H7B	107.9	O3—N2—C3	119.0 (5)
C2—C3—C4	121.5 (4)	O1—C10—H10A	109.5
C2—C3—N2	119.4 (5)	O1—C10—H10B	109.5
C4—C3—N2	119.1 (5)	H10A—C10—H10B	109.5
C4—C5—C6	120.3 (4)	O1—C10—H10C	109.5
C4—C5—H5	119.8	H10A—C10—H10C	109.5
C6—C5—H5	119.8	H10B—C10—H10C	109.5
C5—C4—C3	119.9 (4)	C8—N1—H1A	110.5
C5—C4—H4	120.1	C8—N1—H1B	105.7
C3—C4—H4	120.1	H1A—N1—H1B	121.3
C2—C1—C6	121.8 (4)	C8—N1—H1C	106.3
C2—C1—H1	119.1	H1A—N1—H1C	106.2
C6—C1—H1	119.1	H1B—N1—H1C	105.9
C9—O1—C10	115.2 (4)
C1—C6—C7—C8	75.9 (5)	C10—O1—C9—O2	−1.2 (5)
C5—C6—C7—C8	−104.6 (4)	C10—O1—C9—C8	175.3 (3)
C1—C2—C3—C4	−0.6 (7)	O2—C9—C8—N1	−29.0 (4)
C1—C2—C3—N2	−179.9 (4)	O1—C9—C8—N1	154.3 (3)
C1—C6—C5—C4	−0.8 (6)	O2—C9—C8—C7	91.3 (4)
C7—C6—C5—C4	179.7 (4)	O1—C9—C8—C7	−85.4 (3)
C6—C5—C4—C3	0.1 (7)	C6—C7—C8—N1	−170.5 (3)
C2—C3—C4—C5	0.6 (7)	C6—C7—C8—C9	70.7 (4)
N2—C3—C4—C5	179.9 (4)	C2—C3—N2—O4	178.0 (5)
C3—C2—C1—C6	−0.2 (7)	C4—C3—N2—O4	−1.3 (7)
C5—C6—C1—C2	0.9 (6)	C2—C3—N2—O3	0.6 (7)
C7—C6—C1—C2	−179.7 (4)	C4—C3—N2—O3	−178.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.87	2.61	3.031 (4)	111
N1—H1A···Br1ii	0.87	2.61	3.290 (3)	135
N1—H1B···Br1iii	0.93	2.51	3.303 (3)	143
N1—H1C···Br1iv	1.00	2.55	3.495 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.87	2.61	3.031 (4)	111
N1—H1A⋯Br1ii	0.87	2.61	3.290 (3)	135
N1—H1B⋯Br1iii	0.93	2.51	3.303 (3)	143
N1—H1C⋯Br1iv	1.00	2.55	3.495 (3)	157

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