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In the title compound, C
3H
8NO
2+·C
4H
5O
6−, the
L-alanine molecule exists in the cationic form, with a positively charged amino group and an uncharged carboxylic acid group. The tartaric acid molecule exists in the mono-ionized state. The structure is stabilized by a three-dimensional network of O—H
O and N—H
O hydrogen bonds. No head-to-tail hydrogen bond is observed among the amino acid molecules. The aggregation pattern observed in the structure has striking similarities to those observed in other related amino acid–tartaric acid complexes.
Supporting information
CCDC reference: 200788
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.114
- Data-to-parameter ratio = 6.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
STRVAL_01
From the CIF: _refine_ls_abs_structure_Flack -0.100
From the CIF: _refine_ls_abs_structure_Flack_su 1.900
Alert C Flack test results are meaningless.
PLAT_031 Alert C Refined Extinction Parameter within Range .... 3.21 Sigma
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 24.96
From the CIF: _reflns_number_total 954
Count of symmetry unique reflns 953
Completeness (_total/calc) 100.10%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.001
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
Crystal data top
C3H8NO2+·C4H5O6− | F(000) = 252 |
Mr = 239.18 | Dx = 1.521 Mg m−3 Dm = 1.53 Mg m−3 Dm measured by flotation in a mixture of xylene and carbon tetrachloride |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 5.1446 (8) Å | θ = 2.8–25.0° |
b = 13.721 (3) Å | µ = 0.14 mm−1 |
c = 7.4751 (9) Å | T = 293 K |
β = 98.09 (1)° | Plates, colourless |
V = 522.42 (14) Å3 | 0.35 × 0.30 × 0.15 mm |
Z = 2 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 944 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 2.8° |
ω–2θ scans | h = 0→6 |
Absorption correction: ψ scan (North et al. 1968) | k = 0→16 |
Tmin = 0.952, Tmax = 0.979 | l = −8→8 |
1061 measured reflections | 2 standard reflections every 200 reflections |
954 independent reflections | intensity decay: <2% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0848P)2 + 0.196P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.40 e Å−3 |
954 reflections | Δρmin = −0.30 e Å−3 |
146 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.045 (14) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.1 (19) |
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 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-factorsbased 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.1688 (6) | 0.5120 (3) | 0.7325 (4) | 0.0490 (9) | |
H1 | 0.1520 | 0.4853 | 0.8283 | 0.074* | |
O2 | 0.5462 (5) | 0.5643 (2) | 0.8841 (4) | 0.0434 (7) | |
O3 | 0.1891 (5) | 0.8233 (2) | 1.3666 (3) | 0.0371 (7) | |
H3 | 0.1219 | 0.8269 | 1.4595 | 0.056* | |
O4 | −0.1330 (6) | 0.7148 (3) | 1.2868 (3) | 0.0459 (8) | |
O5 | −0.0059 (5) | 0.6910 (2) | 0.9597 (3) | 0.0355 (6) | |
H5 | −0.1203 | 0.6687 | 1.0140 | 0.053* | |
O6 | −0.1078 (5) | 0.90422 (19) | 0.9821 (3) | 0.0306 (6) | |
H6 | −0.2144 | 0.8816 | 0.9008 | 0.046* | |
O7 | 0.4473 (4) | 0.8258 (2) | 0.7834 (3) | 0.0330 (6) | |
O8 | 0.0315 (4) | 0.8467 (2) | 0.6604 (3) | 0.0329 (6) | |
N1 | 0.6550 (6) | 0.6760 (2) | 0.6067 (4) | 0.0314 (7) | |
H1A | 0.6216 | 0.7198 | 0.6883 | 0.047* | |
H1B | 0.6782 | 0.7063 | 0.5048 | 0.047* | |
H1C | 0.7998 | 0.6431 | 0.6488 | 0.047* | |
C1 | 0.3949 (7) | 0.5587 (3) | 0.7495 (5) | 0.0305 (8) | |
C2 | 0.4315 (8) | 0.6077 (3) | 0.5704 (5) | 0.0354 (8) | |
H2A | 0.2729 | 0.6452 | 0.5277 | 0.042* | |
C3 | 0.4727 (13) | 0.5341 (4) | 0.4281 (7) | 0.0680 (18) | |
H3A | 0.4944 | 0.5673 | 0.3181 | 0.102* | |
H3B | 0.3230 | 0.4918 | 0.4070 | 0.102* | |
H3C | 0.6270 | 0.4964 | 0.4683 | 0.102* | |
C4 | 0.0555 (6) | 0.7650 (3) | 1.2559 (4) | 0.0262 (7) | |
C5 | 0.1493 (6) | 0.7578 (3) | 1.0720 (4) | 0.0256 (7) | |
H5A | 0.3315 | 0.7349 | 1.0893 | 0.031* | |
C6 | 0.1387 (6) | 0.8580 (2) | 0.9813 (4) | 0.0217 (7) | |
H6A | 0.2735 | 0.8992 | 1.0496 | 0.026* | |
C7 | 0.2117 (6) | 0.8436 (2) | 0.7923 (4) | 0.0215 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0533 (18) | 0.060 (2) | 0.0355 (15) | −0.0295 (16) | 0.0111 (12) | 0.0073 (14) |
O2 | 0.0405 (15) | 0.0521 (17) | 0.0370 (15) | −0.0132 (13) | 0.0031 (12) | 0.0158 (13) |
O3 | 0.0431 (13) | 0.0515 (17) | 0.0194 (11) | −0.0106 (13) | 0.0135 (10) | −0.0046 (12) |
O4 | 0.0540 (16) | 0.058 (2) | 0.0300 (13) | −0.0215 (15) | 0.0212 (12) | −0.0022 (12) |
O5 | 0.0498 (14) | 0.0334 (13) | 0.0255 (13) | −0.0115 (12) | 0.0129 (11) | −0.0048 (11) |
O6 | 0.0291 (12) | 0.0371 (14) | 0.0274 (12) | 0.0068 (10) | 0.0105 (9) | −0.0082 (11) |
O7 | 0.0269 (12) | 0.0476 (16) | 0.0269 (11) | 0.0013 (11) | 0.0127 (9) | −0.0042 (11) |
O8 | 0.0300 (12) | 0.0512 (16) | 0.0191 (11) | 0.0002 (12) | 0.0085 (9) | −0.0020 (11) |
N1 | 0.0354 (14) | 0.0376 (16) | 0.0244 (13) | −0.0106 (13) | 0.0154 (11) | 0.0011 (12) |
C1 | 0.0336 (18) | 0.0248 (16) | 0.0356 (18) | −0.0061 (14) | 0.0137 (14) | 0.0002 (15) |
C2 | 0.039 (2) | 0.0349 (19) | 0.0329 (18) | −0.0091 (16) | 0.0083 (14) | 0.0035 (15) |
C3 | 0.110 (5) | 0.056 (3) | 0.045 (3) | −0.043 (3) | 0.037 (3) | −0.020 (2) |
C4 | 0.0292 (15) | 0.0302 (16) | 0.0204 (15) | 0.0014 (15) | 0.0075 (12) | 0.0054 (14) |
C5 | 0.0282 (15) | 0.0313 (18) | 0.0179 (14) | 0.0009 (14) | 0.0055 (11) | −0.0005 (14) |
C6 | 0.0209 (14) | 0.0261 (15) | 0.0193 (14) | −0.0006 (12) | 0.0072 (11) | −0.0040 (12) |
C7 | 0.0260 (15) | 0.0202 (14) | 0.0201 (14) | −0.0028 (13) | 0.0093 (11) | −0.0013 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.319 (5) | N1—H1B | 0.8900 |
O1—H1 | 0.8200 | N1—H1C | 0.8900 |
O2—C1 | 1.185 (5) | C1—C2 | 1.533 (5) |
O3—C4 | 1.279 (4) | C2—C3 | 1.503 (6) |
O3—H3 | 0.8200 | C2—H2A | 0.9800 |
O4—C4 | 1.238 (4) | C3—H3A | 0.9600 |
O5—C5 | 1.412 (4) | C3—H3B | 0.9600 |
O5—H5 | 0.8200 | C3—H3C | 0.9600 |
O6—C6 | 1.418 (4) | C4—C5 | 1.522 (4) |
O6—H6 | 0.8200 | C5—C6 | 1.530 (5) |
O7—C7 | 1.247 (4) | C5—H5A | 0.9800 |
O8—C7 | 1.256 (4) | C6—C7 | 1.525 (4) |
N1—C2 | 1.479 (5) | C6—H6A | 0.9800 |
N1—H1A | 0.8900 | | |
| | | |
C1—O1—H1 | 109.5 | C2—C3—H3C | 109.5 |
C4—O3—H3 | 109.5 | H3A—C3—H3C | 109.5 |
C5—O5—H5 | 109.5 | H3B—C3—H3C | 109.5 |
C6—O6—H6 | 109.5 | O4—C4—O3 | 126.2 (3) |
C2—N1—H1A | 109.5 | O4—C4—C5 | 119.3 (3) |
C2—N1—H1B | 109.5 | O3—C4—C5 | 114.5 (3) |
H1A—N1—H1B | 109.5 | O5—C5—C4 | 110.8 (3) |
C2—N1—H1C | 109.5 | O5—C5—C6 | 109.7 (2) |
H1A—N1—H1C | 109.5 | C4—C5—C6 | 110.2 (3) |
H1B—N1—H1C | 109.5 | O5—C5—H5A | 108.7 |
O2—C1—O1 | 125.4 (3) | C4—C5—H5A | 108.7 |
O2—C1—C2 | 124.5 (3) | C6—C5—H5A | 108.7 |
O1—C1—C2 | 110.1 (3) | O6—C6—C7 | 113.5 (2) |
N1—C2—C3 | 111.9 (4) | O6—C6—C5 | 112.1 (3) |
N1—C2—C1 | 107.8 (3) | C7—C6—C5 | 107.2 (3) |
C3—C2—C1 | 111.8 (4) | O6—C6—H6A | 107.9 |
N1—C2—H2A | 108.4 | C7—C6—H6A | 107.9 |
C3—C2—H2A | 108.4 | C5—C6—H6A | 107.9 |
C1—C2—H2A | 108.4 | O7—C7—O8 | 125.5 (3) |
C2—C3—H3A | 109.5 | O7—C7—C6 | 116.3 (3) |
C2—C3—H3B | 109.5 | O8—C7—C6 | 118.2 (3) |
H3A—C3—H3B | 109.5 | | |
| | | |
O2—C1—C2—N1 | −10.8 (5) | O5—C5—C6—O6 | 72.3 (3) |
O1—C1—C2—N1 | 167.7 (3) | C4—C5—C6—O6 | −49.9 (3) |
O2—C1—C2—C3 | 112.5 (5) | O5—C5—C6—C7 | −52.9 (3) |
O1—C1—C2—C3 | −69.0 (5) | C4—C5—C6—C7 | −175.1 (2) |
O4—C4—C5—O5 | 0.4 (4) | O6—C6—C7—O7 | 163.2 (3) |
O3—C4—C5—O5 | 179.0 (3) | C5—C6—C7—O7 | −72.5 (3) |
O4—C4—C5—C6 | 122.0 (4) | O6—C6—C7—O8 | −19.5 (4) |
O3—C4—C5—C6 | −59.3 (4) | C5—C6—C7—O8 | 104.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O6i | 0.82 | 1.84 | 2.651 (4) | 169 |
O6—H6···O7ii | 0.82 | 1.99 | 2.765 (4) | 158 |
O5—H5···O4 | 0.82 | 2.15 | 2.639 (3) | 119 |
O5—H5···O2ii | 0.82 | 2.34 | 2.878 (4) | 124 |
O3—H3···O8iii | 0.82 | 1.66 | 2.466 (3) | 170 |
N1—H1A···O7 | 0.89 | 1.90 | 2.740 (4) | 157 |
N1—H1C···O5iv | 0.89 | 2.49 | 2.958 (4) | 114 |
N1—H1B···O4v | 0.89 | 2.01 | 2.815 (4) | 149 |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x−1, y, z; (iii) x, y, z+1; (iv) x+1, y, z; (v) x+1, y, z−1. |
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