dl-Asparaginium nitrate.

In the title compound, C(4)H(9)N(2)O(3) (+)·NO(3) (-), alternatively called (1RS)-2-carbamoyl-1-carboxy-ethanaminium nitrate, the asymmetric unit comprises one asparaginium cation and one nitrate anion. The strongest cation-cation O-H⋯O hydrogen bond in the structure, together with other strong cation-cation N-H⋯O hydrogen bonds, generates a succession of infinite chains of R(2) (2)(8) rings along the b axis. Additional cation-cation C-H⋯O hydrogen bonds link these chains into two-dimensional layers formed by alternating R(4) (4)(24) and R(4) (2)(12) rings. Connections between these layers are provided by the strong cation-anion N-H⋯O hydrogen bonds, as well as by one weak C-H⋯O inter-action, thus forming a three-dimensional network. Some of the cation-anion N-H⋯O hydrogen bonds are bifurcated of the type D-H⋯(A(1),A(2)).

Related literature

dl-Asparagine has been used in growth media for bacteria, see: Gerhardt & Wilson (1948 ▶); Palleroni et al. (1973 ▶); Wagtendonk et al. (1963 ▶). For related structures, see Aarthy et al. (2005 ▶); Anitha et al. (2005 ▶); Arnold et al. (2000 ▶); Flaig et al. (2002 ▶); Kartha & de Vries (1961 ▶); Ramanadham et al. (1972 ▶); Smirnova et al. (1990 ▶); Verbist et al. (1972 ▶); Wang et al. (1985 ▶); Weisinger-Lewin et al. (1989 ▶); Yamada et al. (2007 ▶). For hydrogen bonding, see: Desiraju & Steiner (1999 ▶). For hydrogen-bond morifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C4H9N2O3 +·NO3 −

M = 195.14

Monoclinic,

a = 7.923 (2) Å

b = 9.608 (2) Å

c = 10.613 (3) Å

β = 107.105 (2)°

V = 772.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.30 × 0.20 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur–Sapphire2 CCD diffractometer

Absorption correction: gaussian (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.966, T max = 0.991

19446 measured reflections

2236 independent reflections

1804 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.07

2236 reflections

136 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031730/fb2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031730/fb2157Isup2.hkl

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

C4H9N2O3+·NO3−	F(000) = 408
Mr = 195.14	Dx = 1.679 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19446 reflections
a = 7.923 (2) Å	θ = 2.9–30.0°
b = 9.608 (2) Å	µ = 0.16 mm−1
c = 10.613 (3) Å	T = 100 K
β = 107.105 (2)°	Prism, colorless
V = 772.2 (3) Å3	0.3 × 0.2 × 0.09 mm
Z = 4

Oxford Diffraction Xcalibur–Sapphire2 CCD diffractometer	2236 independent reflections
Radiation source: fine-focus sealed tube	1804 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 30.0°, θmin = 2.9°
Absorption correction: gaussian (CrysAlis RED; Oxford Diffraction, 2008)	h = −11→11
Tmin = 0.966, Tmax = 0.991	k = −13→13
19446 measured reflections	l = −11→14

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.1163P] where P = (Fo2 + 2Fc2)/3
2236 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.35366 (11)	1.04131 (8)	0.62255 (8)	0.0171 (2)
H1	0.403 (2)	1.0991 (17)	0.6820 (16)	0.0256*
O2	0.21545 (11)	0.96178 (8)	0.76602 (8)	0.0150 (2)
O3	0.46509 (10)	0.71971 (8)	0.71175 (8)	0.0144 (2)
N2	0.07508 (13)	0.74096 (10)	0.61109 (10)	0.0133 (3)
H1N	0.0164 (19)	0.7751 (15)	0.6650 (14)	0.0158*
H2N	0.1526 (19)	0.6789 (15)	0.6612 (14)	0.0158*
H3N	0.0026 (19)	0.6923 (15)	0.5440 (14)	0.0158*
N3	0.57418 (14)	0.66187 (11)	0.54436 (11)	0.0172 (3)
H4N	0.5623 (19)	0.6635 (16)	0.4621 (16)	0.0207*
H5N	0.659 (2)	0.6100 (16)	0.5979 (15)	0.0207*
C1	0.24959 (14)	0.95636 (10)	0.66154 (11)	0.0118 (3)
C2	0.16701 (14)	0.84965 (10)	0.55565 (10)	0.0111 (3)
H2	0.07526	0.89888	0.48445	0.0134*
C3	0.29888 (14)	0.78621 (11)	0.49291 (10)	0.0129 (3)
H3	0.34226	0.85986	0.44499	0.0154*
H4	0.23798	0.71521	0.42775	0.0154*
C4	0.45449 (14)	0.71962 (10)	0.59194 (11)	0.0117 (3)
O4	0.10171 (10)	0.28059 (8)	0.69646 (8)	0.0164 (2)
O5	0.18243 (12)	0.48467 (9)	0.78126 (9)	0.0228 (3)
O6	0.17667 (12)	0.44085 (9)	0.57939 (9)	0.0204 (3)
N1	0.15474 (12)	0.40279 (9)	0.68709 (9)	0.0132 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0219 (4)	0.0149 (4)	0.0156 (4)	−0.0083 (3)	0.0074 (3)	−0.0035 (3)
O2	0.0182 (4)	0.0129 (3)	0.0149 (4)	−0.0026 (3)	0.0064 (3)	−0.0031 (3)
O3	0.0147 (4)	0.0153 (4)	0.0131 (4)	0.0045 (3)	0.0040 (3)	0.0021 (3)
N2	0.0129 (4)	0.0116 (4)	0.0153 (5)	−0.0020 (3)	0.0042 (4)	−0.0034 (3)
N3	0.0171 (5)	0.0193 (5)	0.0168 (5)	0.0066 (4)	0.0074 (4)	0.0029 (4)
C1	0.0105 (5)	0.0090 (4)	0.0144 (5)	0.0017 (3)	0.0012 (4)	0.0007 (4)
C2	0.0113 (5)	0.0096 (4)	0.0117 (5)	0.0008 (3)	0.0021 (4)	−0.0004 (3)
C3	0.0139 (5)	0.0125 (4)	0.0117 (5)	0.0029 (4)	0.0030 (4)	0.0000 (4)
C4	0.0119 (5)	0.0083 (4)	0.0151 (5)	−0.0003 (3)	0.0043 (4)	0.0010 (4)
O4	0.0158 (4)	0.0115 (4)	0.0222 (4)	−0.0018 (3)	0.0061 (3)	−0.0004 (3)
O5	0.0249 (5)	0.0228 (4)	0.0197 (4)	−0.0048 (3)	0.0049 (4)	−0.0115 (3)
O6	0.0266 (5)	0.0189 (4)	0.0205 (4)	0.0002 (3)	0.0142 (4)	0.0018 (3)
N1	0.0104 (4)	0.0127 (4)	0.0164 (5)	−0.0004 (3)	0.0037 (3)	−0.0027 (3)

O1—C1	1.3107 (16)	N2—H3N	0.903 (14)
O2—C1	1.2173 (16)	N2—H2N	0.907 (15)
O3—C4	1.2494 (16)	N3—H5N	0.893 (16)
O1—H1	0.845 (16)	N3—H4N	0.850 (16)
O4—N1	1.2608 (14)	C1—C2	1.5198 (17)
O5—N1	1.2397 (15)	C2—C3	1.5218 (18)
O6—N1	1.2599 (15)	C3—C4	1.5072 (18)
N2—C2	1.4898 (17)	C2—H2	1.0000
N3—C4	1.3205 (18)	C3—H3	0.9900
N2—H1N	0.899 (15)	C3—H4	0.9900
C1—O1—H1	111.7 (11)	C1—C2—C3	113.09 (9)
H2N—N2—H3N	106.6 (13)	N2—C2—C3	111.74 (8)
C2—N2—H2N	111.5 (10)	N2—C2—C1	109.57 (9)
H1N—N2—H3N	111.3 (14)	C2—C3—C4	113.02 (9)
C2—N2—H1N	113.6 (9)	N3—C4—C3	116.35 (10)
C2—N2—H3N	108.9 (9)	O3—C4—N3	123.27 (11)
H1N—N2—H2N	104.7 (13)	O3—C4—C3	120.38 (10)
C4—N3—H4N	120.7 (11)	N2—C2—H2	107.00
H4N—N3—H5N	119.9 (15)	C1—C2—H2	107.00
C4—N3—H5N	118.8 (10)	C3—C2—H2	107.00
O4—N1—O6	118.68 (9)	C2—C3—H4	109.00
O5—N1—O6	120.55 (9)	H3—C3—H4	108.00
O4—N1—O5	120.76 (9)	C4—C3—H3	109.00
O1—C1—C2	111.14 (9)	C4—C3—H4	109.00
O1—C1—O2	126.15 (10)	C2—C3—H3	109.00
O2—C1—C2	122.67 (10)
O1—C1—C2—N2	170.37 (9)	N2—C2—C3—C4	−67.79 (11)
O1—C1—C2—C3	45.00 (12)	C1—C2—C3—C4	56.40 (11)
O2—C1—C2—N2	−11.93 (15)	C2—C3—C4—O3	0.35 (14)
O2—C1—C2—C3	−137.30 (11)	C2—C3—C4—N3	179.75 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.845 (16)	1.736 (16)	2.571 (2)	169.0 (17)
N2—H1N···O4ii	0.899 (15)	1.962 (15)	2.822 (2)	159.6 (13)
N2—H2N···O3	0.907 (15)	2.406 (16)	2.965 (2)	119.9 (12)
N2—H2N···O5	0.907 (15)	2.233 (14)	3.024 (2)	145.4 (13)
N2—H2N···O6	0.907 (15)	2.474 (15)	3.039 (2)	120.7 (11)
N2—H3N···O4iii	0.903 (14)	2.454 (14)	3.157 (2)	135.0 (12)
N2—H3N···O6iii	0.903 (14)	2.068 (15)	2.957 (2)	168.3 (14)
N3—H5N···O2iv	0.893 (16)	2.064 (15)	2.924 (2)	161.4 (15)
C3—H3···O5v	0.9900	2.3600	3.086 (2)	130.00
C3—H4···O2v	0.9900	2.3900	3.313 (2)	156.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.845 (16)	1.736 (16)	2.571 (2)	169.0 (17)
N2—H1N⋯O4ii	0.899 (15)	1.962 (15)	2.822 (2)	159.6 (13)
N2—H2N⋯O3	0.907 (15)	2.406 (16)	2.965 (2)	119.9 (12)
N2—H2N⋯O5	0.907 (15)	2.233 (14)	3.024 (2)	145.4 (13)
N2—H2N⋯O6	0.907 (15)	2.474 (15)	3.039 (2)	120.7 (11)
N2—H3N⋯O4iii	0.903 (14)	2.454 (14)	3.157 (2)	135.0 (12)
N2—H3N⋯O6iii	0.903 (14)	2.068 (15)	2.957 (2)	168.3 (14)
N3—H5N⋯O2iv	0.893 (16)	2.064 (15)	2.924 (2)	161.4 (15)
C3—H3⋯O5v	0.99	2.36	3.086 (2)	130
C3—H4⋯O2v	0.99	2.39	3.313 (2)	156

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