l-Asparagine-l-tartaric acid (1/1).

In the title compound, C(4)H(8)N(2)O(3)·C(4)H(6)O(6), the amino acid mol-ecule exists as a zwitterion and the carb-oxy-lic acid in an un-ionized state. The tartaric acid mol-ecules are linked into layers parallel to the ab plane by O-H⋯O hydrogen bonds. The amino acid mol-ecules are also linked into layers parallel to the ab plane by N-H⋯O and C-H⋯O hydrogen bonds. The alternating tartaric acid and amino acid layers are linked into a three-dimensional framework by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

Our inter­est in the determination of the structure of the title compound is due to recent advances in organic non-linear optical (NLO) materials on account of their widespread potential industrial applications. For studies on organic non-linear optical materials, see: Cole et al. (2000 ▶); Ravi et al. (1998 ▶); Sarma et al. (1997 ▶).

Experimental

Crystal data

C4H8N2O3·C4H6O6

M = 282.21

Monoclinic,

a = 5.0860 (4) Å

b = 9.6720 (6) Å

c = 11.8340 (8) Å

β = 95.311 (8)°

V = 579.64 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.28 × 0.23 × 0.21 mm

Data collection

Nonius MACH-3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.959, T max = 0.969

1339 measured reflections

1073 independent reflections

1015 reflections with I > 2σ(I)

R int = 0.095

2 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.226

S = 1.38

1073 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030771/ci5134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030771/ci5134Isup2.hkl

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

C4H8N2O3·C4H6O6	F(000) = 296
Mr = 282.21	Dx = 1.617 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 5.0860 (4) Å	θ = 2.7–25°
b = 9.6720 (6) Å	µ = 0.15 mm−1
c = 11.8340 (8) Å	T = 293 K
β = 95.311 (8)°	Block, colourless
V = 579.64 (7) Å3	0.28 × 0.23 × 0.21 mm
Z = 2

Nonius MACH-3 diffractometer	1015 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.095
graphite	θmax = 25.0°, θmin = 2.7°
ω–2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −1→11
Tmin = 0.959, Tmax = 0.969	l = −14→13
1339 measured reflections	2 standard reflections every 60 min
1073 independent reflections	intensity decay: none

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.226	H-atom parameters constrained
S = 1.38	w = 1/[σ2(Fo2) + (0.1143P)2 + 0.7291P] where P = (Fo2 + 2Fc2)/3
1073 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.40 e Å−3

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	0.0957 (12)	0.4538 (7)	0.1832 (5)	0.0531 (18)
O2	0.7732 (11)	0.5170 (7)	0.5295 (5)	0.0459 (16)
O3	0.5946 (13)	0.3196 (8)	0.5798 (5)	0.0544 (18)
N1	0.0876 (12)	0.6710 (7)	0.2495 (5)	0.0377 (16)
H1A	−0.0578	0.6889	0.2091	0.045*
H1B	0.1622	0.7336	0.2930	0.045*
N2	0.2460 (11)	0.3066 (7)	0.4019 (5)	0.0322 (14)
H2A	0.0730	0.3170	0.3847	0.039*
H2B	0.2741	0.2509	0.4617	0.039*
H2C	0.3176	0.2698	0.3430	0.039*
C1	0.6013 (12)	0.4214 (8)	0.5193 (5)	0.0280 (15)
C2	0.3687 (13)	0.4442 (8)	0.4293 (5)	0.0263 (15)
H2	0.2378	0.5013	0.4633	0.032*
C3	0.4415 (14)	0.5175 (8)	0.3216 (6)	0.0333 (17)
H3A	0.5336	0.6030	0.3420	0.040*
H3B	0.5585	0.4592	0.2822	0.040*
C4	0.1954 (14)	0.5483 (8)	0.2447 (6)	0.0328 (16)
O4	0.2756 (10)	−0.0470 (6)	−0.0292 (4)	0.0378 (13)
H4	0.1664	−0.0392	−0.0843	0.057*
O5	0.4110 (10)	0.1599 (6)	−0.0849 (5)	0.0396 (14)
O6	0.8377 (9)	0.1558 (6)	0.0676 (4)	0.0355 (13)
H6	0.7635	0.2283	0.0478	0.053*
O7	0.3467 (9)	0.1735 (7)	0.1895 (4)	0.0385 (14)
H7	0.2136	0.1605	0.1462	0.058*
O8	0.7364 (9)	0.1781 (7)	0.3463 (5)	0.0418 (15)
O9	0.9010 (10)	−0.0231 (6)	0.2943 (5)	0.0378 (14)
H9	1.0049	−0.0102	0.3505	0.057*
C5	0.4314 (12)	0.0606 (9)	−0.0232 (5)	0.0283 (15)
C6	0.6460 (13)	0.0500 (8)	0.0750 (6)	0.0269 (15)
H6A	0.7333	−0.0400	0.0712	0.032*
C7	0.5159 (12)	0.0584 (8)	0.1865 (6)	0.0296 (15)
H7A	0.4173	−0.0268	0.1977	0.035*
C8	0.7309 (12)	0.0778 (8)	0.2842 (5)	0.0274 (16)

	U11	U22	U33	U12	U13	U23
O1	0.054 (4)	0.034 (3)	0.061 (4)	0.011 (3)	−0.043 (3)	−0.010 (3)
O2	0.034 (3)	0.052 (4)	0.047 (3)	−0.006 (3)	−0.025 (2)	0.006 (3)
O3	0.052 (4)	0.050 (4)	0.054 (4)	−0.010 (3)	−0.032 (3)	0.018 (3)
N1	0.034 (3)	0.037 (4)	0.039 (3)	0.002 (3)	−0.017 (3)	−0.002 (3)
N2	0.022 (3)	0.039 (4)	0.033 (3)	−0.003 (3)	−0.009 (2)	−0.001 (3)
C1	0.017 (3)	0.042 (4)	0.023 (3)	0.003 (3)	−0.008 (2)	−0.003 (3)
C2	0.023 (3)	0.033 (4)	0.021 (3)	0.003 (3)	−0.008 (3)	−0.004 (3)
C3	0.027 (3)	0.041 (4)	0.030 (3)	−0.003 (3)	−0.010 (3)	0.005 (3)
C4	0.029 (3)	0.036 (4)	0.031 (3)	−0.001 (3)	−0.011 (3)	0.003 (3)
O4	0.035 (3)	0.033 (3)	0.041 (3)	−0.005 (3)	−0.023 (2)	0.001 (3)
O5	0.034 (3)	0.043 (3)	0.038 (3)	−0.001 (3)	−0.012 (2)	0.008 (3)
O6	0.023 (2)	0.041 (3)	0.040 (3)	−0.004 (2)	−0.0068 (19)	0.001 (3)
O7	0.021 (2)	0.054 (4)	0.037 (3)	0.008 (2)	−0.0123 (19)	−0.008 (3)
O8	0.023 (2)	0.056 (4)	0.044 (3)	0.004 (3)	−0.015 (2)	−0.019 (3)
O9	0.029 (3)	0.041 (3)	0.039 (3)	0.006 (2)	−0.019 (2)	0.000 (3)
C5	0.021 (3)	0.037 (4)	0.026 (3)	0.006 (3)	−0.007 (2)	−0.006 (3)
C6	0.019 (3)	0.029 (3)	0.030 (4)	0.001 (3)	−0.008 (3)	−0.002 (3)
C7	0.019 (3)	0.036 (4)	0.031 (3)	0.002 (3)	−0.011 (2)	−0.001 (3)
C8	0.017 (3)	0.039 (4)	0.025 (3)	−0.002 (3)	−0.005 (2)	0.003 (3)

O1—C4	1.247 (10)	O4—C5	1.306 (10)
O2—C1	1.271 (10)	O4—H4	0.82
O3—C1	1.219 (10)	O5—C5	1.205 (10)
N1—C4	1.311 (11)	O6—C6	1.422 (9)
N1—H1A	0.86	O6—H6	0.82
N1—H1B	0.86	O7—C7	1.409 (9)
N2—C2	1.492 (10)	O7—H7	0.82
N2—H2A	0.89	O8—C8	1.215 (9)
N2—H2B	0.89	O9—C8	1.302 (9)
N2—H2C	0.89	O9—H9	0.82
C1—C2	1.533 (9)	C5—C6	1.522 (9)
C2—C3	1.533 (10)	C6—C7	1.532 (10)
C2—H2	0.98	C6—H6A	0.98
C3—C4	1.507 (9)	C7—C8	1.528 (8)
C3—H3A	0.97	C7—H7A	0.98
C3—H3B	0.97
C4—N1—H1A	120.0	O1—C4—C3	118.6 (7)
C4—N1—H1B	120.0	N1—C4—C3	118.7 (7)
H1A—N1—H1B	120.0	C5—O4—H4	109.5
C2—N2—H2A	109.5	C6—O6—H6	109.5
C2—N2—H2B	109.5	C7—O7—H7	109.5
H2A—N2—H2B	109.5	C8—O9—H9	109.5
C2—N2—H2C	109.5	O5—C5—O4	125.7 (6)
H2A—N2—H2C	109.5	O5—C5—C6	122.1 (7)
H2B—N2—H2C	109.5	O4—C5—C6	112.1 (6)
O3—C1—O2	126.0 (6)	O6—C6—C5	110.6 (6)
O3—C1—C2	117.5 (6)	O6—C6—C7	111.6 (6)
O2—C1—C2	116.2 (7)	C5—C6—C7	108.5 (5)
N2—C2—C3	111.1 (5)	O6—C6—H6A	108.7
N2—C2—C1	107.6 (6)	C5—C6—H6A	108.7
C3—C2—C1	114.5 (5)	C7—C6—H6A	108.7
N2—C2—H2	107.8	O7—C7—C8	106.3 (6)
C3—C2—H2	107.8	O7—C7—C6	112.2 (6)
C1—C2—H2	107.8	C8—C7—C6	108.8 (5)
C4—C3—C2	110.0 (6)	O7—C7—H7A	109.8
C4—C3—H3A	109.7	C8—C7—H7A	109.8
C2—C3—H3A	109.7	C6—C7—H7A	109.8
C4—C3—H3B	109.7	O8—C8—O9	124.4 (6)
C2—C3—H3B	109.7	O8—C8—C7	122.0 (6)
H3A—C3—H3B	108.2	O9—C8—C7	113.6 (6)
O1—C4—N1	122.6 (6)
O3—C1—C2—N2	−24.9 (9)	O5—C5—C6—C7	111.3 (8)
O2—C1—C2—N2	160.4 (6)	O4—C5—C6—C7	−67.4 (8)
O3—C1—C2—C3	−149.0 (7)	O6—C6—C7—O7	70.9 (7)
O2—C1—C2—C3	36.4 (9)	C5—C6—C7—O7	−51.2 (8)
N2—C2—C3—C4	63.9 (8)	O6—C6—C7—C8	−46.4 (8)
C1—C2—C3—C4	−173.9 (6)	C5—C6—C7—C8	−168.5 (6)
C2—C3—C4—O1	−80.7 (9)	O7—C7—C8—O8	−0.7 (9)
C2—C3—C4—N1	95.9 (8)	C6—C7—C8—O8	120.3 (7)
O5—C5—C6—O6	−11.4 (9)	O7—C7—C8—O9	178.5 (6)
O4—C5—C6—O6	170.0 (6)	C6—C7—C8—O9	−60.6 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5i	0.86	2.23	3.053 (8)	160
N1—H1B···O3ii	0.86	2.04	2.856 (9)	159
N2—H2A···O8iii	0.89	2.19	2.895 (8)	136
N2—H2B···O2iv	0.89	2.28	2.921 (9)	129
N2—H2C···O7	0.89	2.06	2.912 (8)	160
N2—H2C···O8	0.89	2.30	2.916 (8)	126
O4—H4···O1v	0.82	1.69	2.500 (6)	168
O6—H6···O4vi	0.82	2.19	2.959 (8)	156
O7—H7···O6iii	0.82	2.05	2.850 (7)	166
O9—H9···O2vii	0.82	1.75	2.570 (7)	180
C2—H2···O2iii	0.98	2.56	3.426 (9)	147
C3—H3A···O3ii	0.97	2.40	3.158 (10)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5i	0.86	2.23	3.053 (8)	160
N1—H1B⋯O3ii	0.86	2.04	2.856 (9)	159
N2—H2A⋯O8iii	0.89	2.19	2.895 (8)	136
N2—H2B⋯O2iv	0.89	2.28	2.921 (9)	129
N2—H2C⋯O7	0.89	2.06	2.912 (8)	160
N2—H2C⋯O8	0.89	2.30	2.916 (8)	126
O4—H4⋯O1v	0.82	1.69	2.500 (6)	168
O6—H6⋯O4vi	0.82	2.19	2.959 (8)	156
O7—H7⋯O6iii	0.82	2.05	2.850 (7)	166
O9—H9⋯O2vii	0.82	1.75	2.570 (7)	180
C2—H2⋯O2iii	0.98	2.56	3.426 (9)	147
C3—H3A⋯O3ii	0.97	2.40	3.158 (10)	134

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