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In the title compound, C3H8NO2+·C2HO4−·0.5H2O, the β-alanine molecule exists in the cationic form and the oxalic acid in the mono-ionized state. The water molecule occurs as a hemihydrate, lying on a twofold axis within the unit cell. The centrosymmetrically related semi-oxalate anions are surrounded by six β-alanine molecules and the complex may be described as an inclusion compound.
Supporting information
CCDC reference: 180778
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.090
- Data-to-parameter ratio = 9.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
PLAT_369 Alert B Long C(sp2)-C(sp2) Bond C4 - C5 = 1.57 Ang.
| Author response: Although the value of C4---C5 (Csp^2^---Csp^2^) bond distance (1.565(2)\%A)
appears a bit larger, it is normal for oxalate anions; c.f. Cambridge
Database.
|
Alert Level C:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 24.95
From the CIF: _reflns_number_total 1424
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 1507
Completeness (_total/calc) 94.49%
Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
β-alaninum oxalate hemihydrate
top
Crystal data top
C3H8NO2+·C2HO4−·0.5H2O | F(000) = 792 |
Mr = 188.14 | Dx = 1.455 Mg m−3 Dm = 1.46 Mg m−3 Dm measured by floatation method |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.373 (3) Å | Cell parameters from 25 reflections |
b = 5.6925 (7) Å | θ = 6–22° |
c = 14.917 (3) Å | µ = 0.14 mm−1 |
β = 115.31 (1)° | T = 293 K |
V = 1717.5 (4) Å3 | Needles, colourless |
Z = 8 | 0.44 × 0.30 × 0.20 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 1189 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω–2θ scans | h = 0→26 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→6 |
Tmin = 0.978, Tmax = 0.996 | l = −16→15 |
1463 measured reflections | 2 standard reflections every 60 min |
1424 independent reflections | intensity decay: <2% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | All H-atom parameters refined |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0401P)2 + 1.2943P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
1424 reflections | Δρmax = 0.21 e Å−3 |
156 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.047 (2) |
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-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 | x | y | z | Uiso*/Ueq | |
O1 | 0.76760 (8) | 0.6585 (3) | 0.89225 (12) | 0.0622 (5) | |
O2 | 0.70405 (7) | 0.5083 (3) | 0.96172 (10) | 0.0551 (4) | |
O3 | 0.57075 (7) | 0.8743 (2) | 0.46900 (9) | 0.0474 (4) | |
O4 | 0.60628 (9) | 0.7253 (2) | 0.63021 (10) | 0.0636 (5) | |
O5 | 0.55133 (7) | 0.4449 (2) | 0.38800 (9) | 0.0472 (4) | |
O6 | 0.58036 (7) | 0.2910 (2) | 0.54699 (9) | 0.0453 (4) | |
O7 | 0.5000 | 0.9153 (3) | 0.7500 | 0.0370 (4) | |
N1 | 0.58851 (8) | 0.2655 (3) | 0.75540 (12) | 0.0383 (4) | |
C1 | 0.72570 (8) | 0.5037 (3) | 0.89562 (13) | 0.0360 (4) | |
C2 | 0.70868 (10) | 0.3203 (4) | 0.81243 (15) | 0.0428 (5) | |
C3 | 0.65435 (9) | 0.1535 (3) | 0.80444 (14) | 0.0393 (4) | |
C4 | 0.58482 (8) | 0.7031 (3) | 0.53656 (12) | 0.0317 (4) | |
C5 | 0.57075 (7) | 0.4576 (3) | 0.48431 (11) | 0.0284 (4) | |
H1O1 | 0.7805 (13) | 0.755 (5) | 0.944 (2) | 0.080 (8)* | |
H1O3 | 0.5760 (12) | 1.022 (5) | 0.5034 (19) | 0.080 (8)* | |
H1N1 | 0.5571 (12) | 0.145 (5) | 0.7417 (17) | 0.065 (7)* | |
H2N1 | 0.5794 (11) | 0.326 (4) | 0.6937 (18) | 0.057 (6)* | |
H3N1 | 0.5843 (10) | 0.373 (4) | 0.7987 (16) | 0.052 (6)* | |
H1C2 | 0.6980 (10) | 0.401 (4) | 0.7487 (17) | 0.055 (6)* | |
H2C2 | 0.7490 (12) | 0.236 (4) | 0.8282 (17) | 0.067 (7)* | |
H1C3 | 0.6530 (9) | 0.025 (4) | 0.7590 (15) | 0.048 (5)* | |
H2C3 | 0.6604 (9) | 0.100 (3) | 0.8736 (15) | 0.044 (5)* | |
H1OW | 0.5177 (11) | 0.822 (4) | 0.8035 (15) | 0.062 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0755 (10) | 0.0652 (10) | 0.0629 (10) | −0.0379 (8) | 0.0458 (9) | −0.0259 (8) |
O2 | 0.0649 (9) | 0.0548 (9) | 0.0605 (9) | −0.0275 (7) | 0.0410 (8) | −0.0253 (7) |
O3 | 0.0823 (10) | 0.0192 (6) | 0.0379 (7) | −0.0002 (6) | 0.0231 (7) | 0.0006 (5) |
O4 | 0.1150 (13) | 0.0289 (7) | 0.0315 (8) | −0.0069 (8) | 0.0164 (8) | −0.0056 (6) |
O5 | 0.0767 (9) | 0.0286 (7) | 0.0325 (7) | −0.0141 (6) | 0.0197 (6) | −0.0069 (5) |
O6 | 0.0777 (10) | 0.0197 (6) | 0.0401 (8) | −0.0009 (6) | 0.0268 (7) | 0.0008 (5) |
O7 | 0.0482 (10) | 0.0236 (8) | 0.0306 (9) | 0.000 | 0.0086 (8) | 0.000 |
N1 | 0.0433 (9) | 0.0371 (9) | 0.0331 (9) | −0.0056 (7) | 0.0150 (7) | −0.0041 (7) |
C1 | 0.0340 (8) | 0.0380 (9) | 0.0347 (9) | −0.0036 (7) | 0.0135 (7) | −0.0025 (7) |
C2 | 0.0427 (11) | 0.0469 (11) | 0.0402 (11) | −0.0032 (8) | 0.0189 (8) | −0.0108 (9) |
C3 | 0.0489 (10) | 0.0291 (9) | 0.0361 (10) | −0.0017 (8) | 0.0144 (8) | −0.0077 (8) |
C4 | 0.0404 (9) | 0.0217 (8) | 0.0307 (9) | −0.0026 (7) | 0.0131 (7) | −0.0014 (7) |
C5 | 0.0346 (8) | 0.0205 (8) | 0.0308 (9) | −0.0031 (6) | 0.0146 (7) | −0.0020 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.303 (2) | N1—H1N1 | 0.94 (3) |
O1—H1O1 | 0.89 (3) | N1—H2N1 | 0.92 (2) |
O2—C1 | 1.271 (2) | N1—H3N1 | 0.93 (2) |
O3—C4 | 1.339 (2) | C1—C2 | 1.540 (3) |
O3—H1O3 | 0.96 (3) | C2—C3 | 1.506 (3) |
O4—C4 | 1.275 (2) | C2—H1C2 | 0.99 (2) |
O5—C5 | 1.313 (2) | C2—H2C2 | 0.96 (3) |
O6—C5 | 1.284 (2) | C3—H1C3 | 0.99 (2) |
O7—H1OW | 0.90 (2) | C3—H2C3 | 1.03 (2) |
N1—C3 | 1.480 (2) | C4—C5 | 1.565 (2) |
| | | |
C1—O1—H1O1 | 111.0 (18) | C1—C2—H2C2 | 105.1 (15) |
C4—O3—H1O3 | 107.2 (15) | H1C2—C2—H2C2 | 106.4 (18) |
C3—N1—H1N1 | 106.8 (14) | N1—C3—C2 | 111.53 (16) |
C3—N1—H2N1 | 113.8 (14) | N1—C3—H1C3 | 104.4 (11) |
H1N1—N1—H2N1 | 103.3 (19) | C2—C3—H1C3 | 107.9 (11) |
C3—N1—H3N1 | 108.5 (13) | N1—C3—H2C3 | 107.4 (10) |
H1N1—N1—H3N1 | 110.2 (19) | C2—C3—H2C3 | 110.5 (11) |
H2N1—N1—H3N1 | 113.9 (19) | H1C3—C3—H2C3 | 114.9 (16) |
O2—C1—O1 | 122.35 (16) | O4—C4—O3 | 127.60 (14) |
O2—C1—C2 | 126.45 (15) | O4—C4—C5 | 122.37 (14) |
O1—C1—C2 | 111.19 (15) | O3—C4—C5 | 110.03 (13) |
C3—C2—C1 | 113.84 (15) | O6—C5—O5 | 129.06 (14) |
C3—C2—H1C2 | 111.2 (12) | O6—C5—C4 | 111.20 (13) |
C1—C2—H1C2 | 109.6 (13) | O5—C5—C4 | 119.74 (13) |
C3—C2—H2C2 | 110.3 (15) | | |
| | | |
O2—C1—C2—C3 | 8.3 (3) | O3—C4—C5—O6 | −176.40 (14) |
O1—C1—C2—C3 | −173.00 (17) | O4—C4—C5—O5 | −177.15 (17) |
C1—C2—C3—N1 | 77.0 (2) | O3—C4—C5—O5 | 3.1 (2) |
O4—C4—C5—O6 | 3.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2i | 0.89 (3) | 1.87 (3) | 2.750 (2) | 170 (3) |
O3—H1O3···O6ii | 0.96 (3) | 1.65 (3) | 2.6098 (17) | 172 (2) |
N1—H1N1···O7iii | 0.94 (3) | 1.87 (3) | 2.787 (2) | 165 (2) |
N1—H2N1···O6 | 0.92 (2) | 2.21 (2) | 3.039 (2) | 150.0 (19) |
N1—H3N1···O5iv | 0.93 (2) | 2.06 (2) | 2.955 (2) | 163.3 (18) |
O7—H1OW···O5iv | 0.90 (2) | 1.91 (2) | 2.7818 (17) | 163 (2) |
C3—H1C3···O4iii | 0.99 (2) | 2.44 (2) | 3.386 (2) | 158.7 (15) |
Symmetry codes: (i) −x+3/2, −y+3/2, −z+2; (ii) x, y+1, z; (iii) x, y−1, z; (iv) x, −y+1, z+1/2. |
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