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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021213/ob6102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021213/ob6102Isup2.hkl
Contains datablock I

CCDC reference: 180778

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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


Amber Alert 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.

Yellow Alert 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

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: 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+·C2HO4·0.5H2OF(000) = 792
Mr = 188.14Dx = 1.455 Mg m3
Dm = 1.46 Mg m3
Dm measured by floatation method
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 22.373 (3) ÅCell parameters from 25 reflections
b = 5.6925 (7) Åθ = 6–22°
c = 14.917 (3) ŵ = 0.14 mm1
β = 115.31 (1)°T = 293 K
V = 1717.5 (4) Å3Needles, colourless
Z = 80.44 × 0.30 × 0.20 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
1189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω–2θ scansh = 026
Absorption correction: ψ scan
(North et al., 1968)
k = 06
Tmin = 0.978, Tmax = 0.996l = 1615
1463 measured reflections2 standard reflections every 60 min
1424 independent reflections intensity decay: <2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033All 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 reflectionsΔρmax = 0.21 e Å3
156 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.76760 (8)0.6585 (3)0.89225 (12)0.0622 (5)
O20.70405 (7)0.5083 (3)0.96172 (10)0.0551 (4)
O30.57075 (7)0.8743 (2)0.46900 (9)0.0474 (4)
O40.60628 (9)0.7253 (2)0.63021 (10)0.0636 (5)
O50.55133 (7)0.4449 (2)0.38800 (9)0.0472 (4)
O60.58036 (7)0.2910 (2)0.54699 (9)0.0453 (4)
O70.50000.9153 (3)0.75000.0370 (4)
N10.58851 (8)0.2655 (3)0.75540 (12)0.0383 (4)
C10.72570 (8)0.5037 (3)0.89562 (13)0.0360 (4)
C20.70868 (10)0.3203 (4)0.81243 (15)0.0428 (5)
C30.65435 (9)0.1535 (3)0.80444 (14)0.0393 (4)
C40.58482 (8)0.7031 (3)0.53656 (12)0.0317 (4)
C50.57075 (7)0.4576 (3)0.48431 (11)0.0284 (4)
H1O10.7805 (13)0.755 (5)0.944 (2)0.080 (8)*
H1O30.5760 (12)1.022 (5)0.5034 (19)0.080 (8)*
H1N10.5571 (12)0.145 (5)0.7417 (17)0.065 (7)*
H2N10.5794 (11)0.326 (4)0.6937 (18)0.057 (6)*
H3N10.5843 (10)0.373 (4)0.7987 (16)0.052 (6)*
H1C20.6980 (10)0.401 (4)0.7487 (17)0.055 (6)*
H2C20.7490 (12)0.236 (4)0.8282 (17)0.067 (7)*
H1C30.6530 (9)0.025 (4)0.7590 (15)0.048 (5)*
H2C30.6604 (9)0.100 (3)0.8736 (15)0.044 (5)*
H1OW0.5177 (11)0.822 (4)0.8035 (15)0.062 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0755 (10)0.0652 (10)0.0629 (10)0.0379 (8)0.0458 (9)0.0259 (8)
O20.0649 (9)0.0548 (9)0.0605 (9)0.0275 (7)0.0410 (8)0.0253 (7)
O30.0823 (10)0.0192 (6)0.0379 (7)0.0002 (6)0.0231 (7)0.0006 (5)
O40.1150 (13)0.0289 (7)0.0315 (8)0.0069 (8)0.0164 (8)0.0056 (6)
O50.0767 (9)0.0286 (7)0.0325 (7)0.0141 (6)0.0197 (6)0.0069 (5)
O60.0777 (10)0.0197 (6)0.0401 (8)0.0009 (6)0.0268 (7)0.0008 (5)
O70.0482 (10)0.0236 (8)0.0306 (9)0.0000.0086 (8)0.000
N10.0433 (9)0.0371 (9)0.0331 (9)0.0056 (7)0.0150 (7)0.0041 (7)
C10.0340 (8)0.0380 (9)0.0347 (9)0.0036 (7)0.0135 (7)0.0025 (7)
C20.0427 (11)0.0469 (11)0.0402 (11)0.0032 (8)0.0189 (8)0.0108 (9)
C30.0489 (10)0.0291 (9)0.0361 (10)0.0017 (8)0.0144 (8)0.0077 (8)
C40.0404 (9)0.0217 (8)0.0307 (9)0.0026 (7)0.0131 (7)0.0014 (7)
C50.0346 (8)0.0205 (8)0.0308 (9)0.0031 (6)0.0146 (7)0.0020 (7)
Geometric parameters (Å, º) top
O1—C11.303 (2)N1—H1N10.94 (3)
O1—H1O10.89 (3)N1—H2N10.92 (2)
O2—C11.271 (2)N1—H3N10.93 (2)
O3—C41.339 (2)C1—C21.540 (3)
O3—H1O30.96 (3)C2—C31.506 (3)
O4—C41.275 (2)C2—H1C20.99 (2)
O5—C51.313 (2)C2—H2C20.96 (3)
O6—C51.284 (2)C3—H1C30.99 (2)
O7—H1OW0.90 (2)C3—H2C31.03 (2)
N1—C31.480 (2)C4—C51.565 (2)
C1—O1—H1O1111.0 (18)C1—C2—H2C2105.1 (15)
C4—O3—H1O3107.2 (15)H1C2—C2—H2C2106.4 (18)
C3—N1—H1N1106.8 (14)N1—C3—C2111.53 (16)
C3—N1—H2N1113.8 (14)N1—C3—H1C3104.4 (11)
H1N1—N1—H2N1103.3 (19)C2—C3—H1C3107.9 (11)
C3—N1—H3N1108.5 (13)N1—C3—H2C3107.4 (10)
H1N1—N1—H3N1110.2 (19)C2—C3—H2C3110.5 (11)
H2N1—N1—H3N1113.9 (19)H1C3—C3—H2C3114.9 (16)
O2—C1—O1122.35 (16)O4—C4—O3127.60 (14)
O2—C1—C2126.45 (15)O4—C4—C5122.37 (14)
O1—C1—C2111.19 (15)O3—C4—C5110.03 (13)
C3—C2—C1113.84 (15)O6—C5—O5129.06 (14)
C3—C2—H1C2111.2 (12)O6—C5—C4111.20 (13)
C1—C2—H1C2109.6 (13)O5—C5—C4119.74 (13)
C3—C2—H2C2110.3 (15)
O2—C1—C2—C38.3 (3)O3—C4—C5—O6176.40 (14)
O1—C1—C2—C3173.00 (17)O4—C4—C5—O5177.15 (17)
C1—C2—C3—N177.0 (2)O3—C4—C5—O53.1 (2)
O4—C4—C5—O63.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···O2i0.89 (3)1.87 (3)2.750 (2)170 (3)
O3—H1O3···O6ii0.96 (3)1.65 (3)2.6098 (17)172 (2)
N1—H1N1···O7iii0.94 (3)1.87 (3)2.787 (2)165 (2)
N1—H2N1···O60.92 (2)2.21 (2)3.039 (2)150.0 (19)
N1—H3N1···O5iv0.93 (2)2.06 (2)2.955 (2)163.3 (18)
O7—H1OW···O5iv0.90 (2)1.91 (2)2.7818 (17)163 (2)
C3—H1C3···O4iii0.99 (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, y1, z; (iv) x, y+1, z+1/2.
 

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