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In the title salt, C5H10NO2+·C4H5O6-, proline exists as a cation and the tartaric acid as a semi-tartrate anion. The semi-tartrate ions form hydrogen-bonded strings along the c axis. These strings are interconnected through the proline mol­ecules, forming a layered network parallel to the bc plane. The proline mol­ecules, however, do not directly interact among themselves, except for a weak C-H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100020370/vj1124sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020370/vj1124Isup2.hkl
Contains datablock I

CCDC reference: 163910

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: SHELXS93 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

L-prolinium tartrate top
Crystal data top
C5H10NO2+·C4H5O6F(000) = 284
Mr = 267.24Dx = 1.551 Mg m3
Dm = 1.55 Mg m3
Dm measured by flotation
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
a = 5.007 (1) ÅCell parameters from 25 reflections
b = 17.676 (3) Åθ = 16–26°
c = 6.523 (1) ŵ = 1.21 mm1
β = 100.40 (2)°T = 293 K
V = 567.8 (2) Å3Needles, colourless
Z = 20.42 × 0.35 × 0.21 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
968 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 67.9°, θmin = 5.0°
ω/2θ scansh = 06
Absorption correction: ψ-scan
(North et al., 1968)
k = 017
Tmin = 0.540, Tmax = 0.734l = 76
1077 measured reflections2 standard reflections every 200 reflections
974 independent reflections intensity decay: 0.1%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.028 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.1468P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.16 e Å3
974 reflectionsΔρmin = 0.18 e Å3
178 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.060 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.1 (3)
Special details top

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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*/UeqOcc. (<1)
O10.8186 (4)0.47409 (14)0.7398 (4)0.0494 (6)
H10.96010.49480.79450.074*
O21.0870 (4)0.37594 (16)0.7105 (4)0.0626 (8)
O30.9331 (3)0.60674 (11)0.4467 (3)0.0341 (4)
H111.05950.61860.53950.051*
O40.7627 (3)0.71715 (10)0.5289 (3)0.0313 (4)
O50.3369 (3)0.70372 (10)0.2185 (3)0.0293 (4)
H130.18760.69000.15630.044*
O60.7794 (3)0.67500 (11)0.0068 (3)0.0323 (5)
H150.74370.68000.13380.048*
O70.3422 (4)0.63018 (12)0.2814 (3)0.0364 (5)
O80.2251 (4)0.54422 (12)0.0614 (3)0.0412 (5)
N10.7154 (4)0.30306 (13)0.4339 (3)0.0333 (5)
H90.88760.29110.49060.040*
H100.60820.26360.45130.040*
C10.8727 (5)0.40807 (17)0.6720 (4)0.0335 (6)
C20.6270 (5)0.37223 (16)0.5379 (4)0.0320 (6)
H20.49460.35800.62490.038*
C30.4903 (7)0.4213 (2)0.3576 (5)0.0559 (9)
H30.29930.40870.31820.067*
H40.50750.47450.39330.067*
C40.6384 (12)0.4030 (3)0.1897 (8)0.0509 (17)0.711 (13)
H50.80670.43140.20600.061*0.711 (13)
H60.52950.41500.05510.061*0.711 (13)
C4'0.468 (3)0.3750 (7)0.1615 (17)0.049 (4)0.289 (13)
H5'0.29440.34900.13130.059*0.289 (13)
H6'0.48680.40670.04360.059*0.289 (13)
C50.6948 (8)0.3199 (2)0.2070 (5)0.0480 (8)
H70.86320.30780.16070.058*
H80.54840.29130.12440.058*
C60.7511 (5)0.65955 (14)0.4242 (3)0.0240 (5)
C70.5137 (4)0.64074 (14)0.2524 (3)0.0231 (5)
H120.41420.59820.29900.028*
C80.6173 (5)0.61642 (14)0.0548 (3)0.0245 (5)
H140.73100.57140.08750.029*
C90.3727 (5)0.59527 (14)0.1118 (4)0.0261 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0382 (10)0.0446 (14)0.0639 (15)0.0046 (10)0.0054 (10)0.0201 (11)
O20.0307 (10)0.0664 (17)0.0847 (19)0.0062 (11)0.0059 (11)0.0291 (15)
O30.0312 (9)0.0383 (11)0.0273 (9)0.0072 (8)0.0098 (7)0.0052 (8)
O40.0313 (8)0.0329 (11)0.0273 (9)0.0030 (7)0.0009 (7)0.0081 (7)
O50.0254 (8)0.0306 (10)0.0291 (9)0.0044 (7)0.0024 (7)0.0028 (7)
O60.0281 (8)0.0440 (11)0.0233 (8)0.0089 (8)0.0008 (6)0.0010 (8)
O70.0311 (9)0.0501 (13)0.0242 (10)0.0035 (8)0.0056 (7)0.0033 (8)
O80.0445 (11)0.0392 (12)0.0359 (11)0.0141 (9)0.0034 (8)0.0027 (8)
N10.0336 (10)0.0260 (13)0.0394 (12)0.0031 (9)0.0041 (9)0.0015 (9)
C10.0279 (12)0.0396 (16)0.0343 (14)0.0026 (11)0.0091 (10)0.0029 (12)
C20.0271 (11)0.0308 (15)0.0377 (15)0.0014 (11)0.0048 (10)0.0014 (11)
C30.0598 (18)0.041 (2)0.059 (2)0.0145 (15)0.0113 (15)0.0005 (15)
C40.057 (4)0.046 (3)0.044 (3)0.006 (3)0.006 (2)0.017 (2)
C4'0.063 (9)0.036 (7)0.039 (7)0.006 (6)0.016 (5)0.004 (5)
C50.060 (2)0.047 (2)0.0356 (16)0.0045 (15)0.0050 (14)0.0038 (13)
C60.0247 (10)0.0272 (14)0.0192 (11)0.0030 (9)0.0017 (8)0.0021 (9)
C70.0224 (10)0.0254 (12)0.0198 (12)0.0016 (9)0.0004 (8)0.0006 (9)
C80.0241 (10)0.0257 (13)0.0216 (12)0.0008 (9)0.0013 (9)0.0017 (9)
C90.0246 (11)0.0269 (14)0.0250 (13)0.0001 (10)0.0002 (9)0.0061 (10)
Geometric parameters (Å, º) top
O1—C11.294 (4)C2—H20.9800
O1—H10.8200C3—C41.465 (6)
O2—C11.200 (4)C3—C4'1.505 (12)
O3—C61.294 (3)C3—H30.9700
O3—H110.8200C3—H40.9700
O4—C61.221 (3)C4—C51.495 (6)
O5—C71.415 (3)C4—H50.9700
O5—H130.8200C4—H60.9700
O6—C81.418 (3)C4'—C51.484 (13)
O6—H150.8200C4'—H5'0.9700
O7—C91.252 (3)C4'—H6'0.9700
O8—C91.248 (3)C5—H70.9700
N1—C51.495 (4)C5—H80.9700
N1—C21.503 (3)C6—C71.516 (3)
N1—H90.9000C7—C81.535 (3)
N1—H100.9000C7—H120.9800
C1—C21.513 (4)C8—C91.530 (3)
C2—C31.521 (4)C8—H140.9800
C1—O1—H1109.5C5—C4'—C3104.4 (7)
C6—O3—H11109.5C5—C4'—H5'110.9
C7—O5—H13109.5C3—C4'—H5'110.9
C8—O6—H15109.5C5—C4'—H6'110.9
C5—N1—C2108.1 (2)C3—C4'—H6'110.9
C5—N1—H9110.1H5'—C4'—H6'108.9
C2—N1—H9110.1C4'—C5—C438.2 (5)
C5—N1—H10110.1C4'—C5—N1104.0 (5)
C2—N1—H10110.1C4—C5—N1104.4 (3)
H9—N1—H10108.4C4'—C5—H7139.4
O2—C1—O1126.1 (3)C4—C5—H7110.9
O2—C1—C2121.7 (3)N1—C5—H7110.9
O1—C1—C2112.1 (2)C4'—C5—H875.9
N1—C2—C1109.1 (2)C4—C5—H8110.9
N1—C2—C3104.0 (2)N1—C5—H8110.9
C1—C2—C3114.4 (3)H7—C5—H8108.9
N1—C2—H2109.7O4—C6—O3125.2 (2)
C1—C2—H2109.7O4—C6—C7123.2 (2)
C3—C2—H2109.7O3—C6—C7111.6 (2)
C4—C3—C4'38.3 (5)O5—C7—C6109.15 (19)
C4—C3—C2103.6 (3)O5—C7—C8112.70 (19)
C4'—C3—C2107.5 (5)C6—C7—C8110.09 (17)
C4—C3—H3111.1O5—C7—H12108.3
C4'—C3—H374.4C6—C7—H12108.3
C2—C3—H3111.1C8—C7—H12108.3
C4—C3—H4111.1O6—C8—C9113.78 (18)
C4'—C3—H4136.2O6—C8—C7109.32 (19)
C2—C3—H4111.1C9—C8—C7108.45 (17)
H3—C3—H4109.0O6—C8—H14108.4
C3—C4—C5105.9 (4)C9—C8—H14108.4
C3—C4—H5110.5C7—C8—H14108.4
C5—C4—H5110.5O8—C9—O7127.3 (2)
C3—C4—H6110.5O8—C9—C8115.2 (2)
C5—C4—H6110.5O7—C9—C8117.5 (2)
H5—C4—H6108.7
C5—N1—C2—C1108.9 (3)C3—C4—C5—C4'65.0 (8)
C5—N1—C2—C313.7 (3)C3—C4—C5—N129.5 (5)
O2—C1—C2—N111.8 (4)C2—N1—C5—C4'30.4 (7)
O1—C1—C2—N1169.8 (2)C2—N1—C5—C49.0 (4)
O2—C1—C2—C3127.8 (3)O4—C6—C7—O57.8 (3)
O1—C1—C2—C353.8 (3)O3—C6—C7—O5173.38 (18)
N1—C2—C3—C431.6 (4)O4—C6—C7—C8132.0 (2)
C1—C2—C3—C487.4 (4)O3—C6—C7—C849.2 (3)
N1—C2—C3—C4'8.1 (7)O5—C7—C8—O664.7 (2)
C1—C2—C3—C4'127.0 (7)C6—C7—C8—O657.4 (2)
C4'—C3—C4—C563.1 (8)O5—C7—C8—C959.9 (2)
C2—C3—C4—C538.2 (5)C6—C7—C8—C9178.0 (2)
C4—C3—C4'—C563.0 (8)O6—C8—C9—O8179.5 (2)
C2—C3—C4'—C526.7 (10)C7—C8—C9—O857.6 (3)
C3—C4'—C5—C461.1 (8)O6—C8—C9—O70.6 (3)
C3—C4'—C5—N134.5 (9)C7—C8—C9—O7122.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O8i0.821.722.531 (3)170
N1—H9···O4ii0.902.212.994 (3)146
N1—H10···O4iii0.902.062.881 (3)152
O3—H11···O7i0.821.682.490 (2)171
O5—H13···O6iv0.822.142.954 (2)170
O6—H15···O4v0.822.313.105 (3)162
C2—H2···O2iv0.982.233.112 (3)149
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y1/2, z+1; (iii) x+1, y1/2, z+1; (iv) x1, y, z; (v) x, y, z1.
 

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