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In the title compound, C3H8NO2+·C4H5O6-, the sarcosinium cation and semi-tartrate anion are held together by a three-dimensional network of O-H...O, N-H...O and C-H...O hydrogen bonds. The structure may be described as an inclusion compound with the semi-tartrate anion as the host and the sarcosinium cation as the guest.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100012440/vj1116sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100012440/vj1116Isup2.hkl
Contains datablock I

CCDC reference: 159986

Comment top

Single-crystal X-ray investigations on complexes of amino acids with carboxylic acids are interesting in view of their geometrical features and aggregation patterns that might possibly have occurred in prebiotic polymerization (Vijayan, 1988; Prasad & Vijayan, 1993). The present study reports the crystal structure of a complex, (I), of sarcosine with tartaric acid. Sarcosine (N-methylglycine, CH3NH2+CH2COO-) is an α-amino acid present in several biologically important compounds and its crystal structure was elucidated in our laboratory (Mostad & Natarajan, 1989). \sch

The sarcosine moiety exists in the cationic form with a positively charged amino group and a neutral carboxylic acid group. The C1—C2—N1—C3 chain deviates greatly from planarity as the torsion angle about the C2—N1 bond is -67.2 (2)°, indicating that the methyl group exists in the synclinal conformation with respect to C1.

The tartaric acid molecule (Okaya et al., 1966) exists here as a semi-tartrate ion with a neutral carboxylic acid group and a negatively charged carboxylate ion. The C4—O3 and C4O4 bond distances [1.288 (3) and 1.222 (3) Å, respectively] of the neutral carboxylic acid group are significantly different from those expected. The decrease in the C—O and increase in the CO bond lengths may be attributed to a strong O3—H3···O7(x - 1, y + 1, z) hydrogen bond observed in the crystal structure, with an O···O distance of 2.488 (2) Å. This observation is supported by the fact that strong O—H···X hydrogen bonds involving the carboxylic acid group O atom as donor permit some double-bond character to the C—O and some single-bond character to CO (Hahn, 1957). The angle between the planes of the half molecules (O3/O4/C4/C5/O5 and O7/O8/C6/C7/O6) is 65.10 (7)°, which is somewhat larger than the value of 54.6 (4)° found in the structure of tartaric acid. The carbon skeleton of the semi-tartrate anion is essentially planar [torsion angle C4—C5—C6—C7 179.21 (15)°].

The crystal structure (Fig. 2) is stabilized by hydrogen bonds (Table 1). The semi-tartrate ions aggregate into layers parallel to the ab plane. The layers are interconnected by sarcosinium Ccations which do not directly interact among themselves except for the presence of a weak C—H···O hydrogen bond. The crystal structure can be described as an inclusion compound with the semi-tartrate anion as the host and the sarcosinium cation as the guest.

Related literature top

For related literature, see: Hahn (1957); Mostad & Natarajan (1989); Okaya et al. (1966); Prasad & Vijayan (1993); Vijayan (1988).

Experimental top

Colourless single crystals of the title complex were grown as transparent plates from a saturated aqueous solution containing sarcosine and tartaric acid in a 1:1 stoichiometric ratio.

Refinement top

All the H atoms were located from a difference Fourier map and then allowed for as riding atoms (C—H 0.96–0.98, N—H 0.90 and O—H 0.82 Å). The absolute configuration of this light-atom structure was not established by the analysis but is known from the configuration of the starting reagents.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1993); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atom-numbering scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A view showing some of the O—H.·O and N—H···O hydrogen bonds in (I).
sarcosinium tartrate top
Crystal data top
C3H8NO2+·C4H5O6Z = 1
Mr = 239.18F(000) = 126
Triclinic, P1Dx = 1.549 Mg m3
Dm = 1.54 Mg m3
Dm measured by flotation in carbon tetrachloride/xylene
a = 5.0038 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.442 (2) ÅCell parameters from 25 reflections
c = 8.3179 (11) Åθ = 4–17°
α = 78.60 (2)°µ = 0.14 mm1
β = 80.62 (2)°T = 293 K
γ = 79.80 (2)°Plate, colourless
V = 256.40 (11) Å30.45 × 0.30 × 0.20 mm
Data collection top
Enraf-Nonius sealed tube
diffractometer
Rint = 0.032
Radiation source: fine-focus sealed tubeθmax = 24.9°, θmin = 2.5°
Graphite monochromatorh = 05
/w–2/q scansk = 77
1012 measured reflectionsl = 99
897 independent reflections2 standard reflections every 200 reflections
897 reflections with I > 2σ(I) intensity decay: 0.1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.0215P]
where P = (Fo2 + 2Fc2)/3
897 reflections(Δ/σ)max < 0.001
150 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = 0.19 e Å3
Crystal data top
C3H8NO2+·C4H5O6γ = 79.80 (2)°
Mr = 239.18V = 256.40 (11) Å3
Triclinic, P1Z = 1
a = 5.0038 (15) ÅMo Kα radiation
b = 6.442 (2) ŵ = 0.14 mm1
c = 8.3179 (11) ÅT = 293 K
α = 78.60 (2)°0.45 × 0.30 × 0.20 mm
β = 80.62 (2)°
Data collection top
Enraf-Nonius sealed tube
diffractometer
Rint = 0.032
1012 measured reflections2 standard reflections every 200 reflections
897 independent reflections intensity decay: 0.1%
897 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0253 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 1.09Δρmax = 0.18 e Å3
897 reflectionsΔρmin = 0.19 e Å3
150 parameters
Special details top

Experimental. 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.0485 (3)0.4666 (2)0.07007 (19)0.0354 (4)
H30.17350.56120.09330.053*
O40.0500 (3)0.4743 (2)0.32013 (18)0.0320 (4)
O50.4989 (3)0.1832 (2)0.28080 (17)0.0295 (3)
H50.65560.13090.24910.044*
O60.0631 (3)0.0296 (2)0.2265 (2)0.0328 (4)
H60.08480.16010.23360.049*
O70.5211 (3)0.2879 (2)0.1359 (2)0.0366 (4)
O80.6747 (3)0.0335 (3)0.0633 (2)0.0422 (4)
C40.1002 (4)0.4092 (3)0.1885 (2)0.0230 (4)
C50.3492 (4)0.2473 (3)0.1451 (2)0.0230 (4)
H5A0.46600.31580.05050.028*
C60.2535 (4)0.0579 (3)0.0958 (2)0.0240 (4)
H6A0.16000.11150.00240.029*
C70.5052 (4)0.1019 (3)0.0502 (2)0.0249 (4)
O10.1266 (4)0.8718 (3)0.7568 (3)0.0524 (5)
H10.02060.87330.81700.079*
O20.0014 (4)0.5979 (3)0.6783 (2)0.0520 (5)
N10.5001 (4)0.4999 (3)0.5004 (2)0.0308 (4)
H1A0.36090.48290.45030.037*
H1B0.64880.50700.42360.037*
C10.1595 (4)0.7180 (4)0.6725 (3)0.0327 (5)
C20.4290 (4)0.7057 (3)0.5633 (3)0.0318 (5)
H2A0.42080.82350.47050.038*
H2B0.57110.72020.62510.038*
C30.5565 (6)0.3089 (4)0.6298 (3)0.0431 (6)
H3A0.68850.33270.69350.065*
H3B0.62760.18590.57840.065*
H3C0.38990.28450.70140.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0346 (8)0.0313 (8)0.0364 (8)0.0139 (6)0.0082 (6)0.0106 (6)
O40.0238 (8)0.0367 (8)0.0361 (8)0.0012 (6)0.0021 (6)0.0178 (6)
O50.0193 (7)0.0346 (8)0.0346 (7)0.0026 (6)0.0049 (6)0.0111 (6)
O60.0242 (7)0.0231 (7)0.0478 (9)0.0023 (6)0.0054 (6)0.0077 (6)
O70.0279 (8)0.0227 (7)0.0523 (9)0.0051 (6)0.0014 (7)0.0033 (6)
O80.0397 (9)0.0346 (8)0.0410 (9)0.0064 (7)0.0124 (7)0.0049 (7)
C40.0225 (9)0.0171 (8)0.0280 (9)0.0026 (7)0.0017 (7)0.0050 (7)
C50.0206 (9)0.0194 (9)0.0274 (9)0.0002 (7)0.0004 (7)0.0057 (7)
C60.0234 (9)0.0196 (9)0.0286 (9)0.0006 (7)0.0025 (7)0.0073 (7)
C70.0228 (10)0.0216 (9)0.0301 (10)0.0027 (7)0.0039 (7)0.0085 (8)
O10.0378 (10)0.0583 (11)0.0659 (13)0.0108 (8)0.0153 (9)0.0371 (10)
O20.0260 (8)0.0789 (14)0.0622 (12)0.0182 (8)0.0054 (7)0.0388 (11)
N10.0255 (9)0.0354 (9)0.0295 (8)0.0012 (7)0.0010 (7)0.0076 (8)
C10.0220 (10)0.0463 (12)0.0310 (11)0.0009 (9)0.0042 (8)0.0127 (9)
C20.0272 (11)0.0325 (11)0.0346 (10)0.0024 (9)0.0003 (9)0.0091 (9)
C30.0491 (15)0.0362 (12)0.0419 (13)0.0048 (10)0.0103 (11)0.0003 (10)
Geometric parameters (Å, º) top
O3—C41.288 (3)O1—C11.297 (3)
O3—H30.82O1—H10.82
O4—C41.222 (3)O2—C11.201 (3)
O5—C51.410 (2)N1—C31.485 (3)
O5—H50.82N1—C21.485 (3)
O6—C61.421 (2)N1—H1A0.90
O6—H60.82N1—H1B0.90
O7—C71.264 (3)C1—C21.497 (3)
O8—C71.230 (3)C2—H2A0.97
C4—C51.521 (2)C2—H2B0.97
C5—C61.535 (3)C3—H3A0.96
C5—H5A0.98C3—H3B0.96
C6—C71.526 (3)C3—H3C0.96
C6—H6A0.98
C4—O3—H3109.5C3—N1—C2114.31 (18)
C5—O5—H5109.5C3—N1—H1A108.7
C6—O6—H6109.5C2—N1—H1A108.7
O4—C4—O3125.00 (18)C3—N1—H1B108.7
O4—C4—C5123.51 (18)C2—N1—H1B108.7
O3—C4—C5111.49 (16)H1A—N1—H1B107.6
O5—C5—C4109.31 (15)O2—C1—O1125.7 (2)
O5—C5—C6112.34 (15)O2—C1—C2122.8 (2)
C4—C5—C6109.02 (15)O1—C1—C2111.4 (2)
O5—C5—H5A108.7N1—C2—C1111.55 (18)
C4—C5—H5A108.7N1—C2—H2A109.3
C6—C5—H5A108.7C1—C2—H2A109.3
O6—C6—C7113.96 (15)N1—C2—H2B109.3
O6—C6—C5109.09 (16)C1—C2—H2B109.3
C7—C6—C5108.55 (16)H2A—C2—H2B108.0
O6—C6—H6A108.4N1—C3—H3A109.5
C7—C6—H6A108.4N1—C3—H3B109.5
C5—C6—H6A108.4H3A—C3—H3B109.5
O8—C7—O7126.99 (18)N1—C3—H3C109.5
O8—C7—C6116.21 (17)H3A—C3—H3C109.5
O7—C7—C6116.76 (17)H3B—C3—H3C109.5
C1—O1—H1109.5
O4—C4—C5—O52.0 (3)O6—C6—C7—O8179.50 (17)
O3—C4—C5—O5177.64 (16)C5—C6—C7—O858.7 (2)
O4—C4—C5—C6125.2 (2)O6—C6—C7—O72.5 (3)
O3—C4—C5—C654.5 (2)C5—C6—C7—O7119.23 (19)
O5—C5—C6—O665.2 (2)C3—N1—C2—C167.0 (2)
C4—C5—C6—O656.08 (19)O2—C1—C2—N114.7 (3)
O5—C5—C6—C759.5 (2)O1—C1—C2—N1165.27 (19)
C4—C5—C6—C7179.21 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O8i0.821.762.548 (2)161
O3—H3···O7ii0.821.682.488 (2)166
O5—H5···O6iii0.822.112.918 (2)167
O6—H6···O4iv0.822.353.146 (2)163
N1—H1A···O40.902.052.946 (2)174
N1—H1B···O4iii0.902.042.905 (2)160
C2—H2B···O2iii0.972.233.074 (3)145
Symmetry codes: (i) x1, y+1, z+1; (ii) x1, y+1, z; (iii) x+1, y, z; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC3H8NO2+·C4H5O6
Mr239.18
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.0038 (15), 6.442 (2), 8.3179 (11)
α, β, γ (°)78.60 (2), 80.62 (2), 79.80 (2)
V3)256.40 (11)
Z1
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.45 × 0.30 × 0.20
Data collection
DiffractometerEnraf-Nonius sealed tube
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
1012, 897, 897
Rint0.032
(sin θ/λ)max1)0.593
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.066, 1.09
No. of reflections897
No. of parameters150
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.19

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1993), PLATON (Spek, 1999), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O8i0.821.762.548 (2)161
O3—H3···O7ii0.821.682.488 (2)166
O5—H5···O6iii0.822.112.918 (2)167
O6—H6···O4iv0.822.353.146 (2)163
N1—H1A···O40.902.052.946 (2)174
N1—H1B···O4iii0.902.042.905 (2)160
C2—H2B···O2iii0.972.233.074 (3)145
Symmetry codes: (i) x1, y+1, z+1; (ii) x1, y+1, z; (iii) x+1, y, z; (iv) x, y1, z.
 

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