In the title compound, 2C3H8NO3+·.C2O42-·2H2O, the serine molecule exists in the cationic form with an uncharged carboxylic acid group and a positively charged amino group. The oxalic acid molecule exists as a double negatively charged oxalate anion. Two independent oxalate anions lie across inversion centres. The aggregation of individual molecules differs distinctly from other similar complexes.
Supporting information
CCDC reference: 180777
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.099
- Data-to-parameter ratio = 11.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C(4) - C(4)a = 1.56 Ang.
PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C(4') - C(4')b = 1.56 Ang.
General Notes
FORMU_01 There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C8 H20 N2 O12
Atom count from _chemical_formula_moiety:C5 H12 N1 O38
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, 1997); 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
C3H8NO3+2·C2O42−·2H2O | F(000) = 712 |
Mr = 336.26 | Dx = 1.554 Mg m−3 Dm = 1.56 Mg m−3 Dm measured by floatation |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
a = 4.8685 (10) Å | Cell parameters from 25 reflections |
b = 17.199 (7) Å | θ = 36–45° |
c = 17.172 (4) Å | µ = 1.32 mm−1 |
β = 91.678 (19)° | T = 293 K |
V = 1437.2 (7) Å3 | Needles, colourless |
Z = 4 | 0.35 × 0.20 × 0.15 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.033 |
Radiation source: fine-focus sealed tube | θmax = 67.9°, θmin = 3.6° |
Graphite monochromator | h = −5→0 |
ω–2θ scans | k = 0→20 |
3513 measured reflections | l = −20→20 |
2616 independent reflections | 2 standard reflections every 200 reflections |
2528 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0525P)2 + 0.5233P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
2616 reflections | Δρmax = 0.25 e Å−3 |
232 parameters | Δρmin = −0.29 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: 0.0521 (17) |
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 | 0.6644 (2) | 0.52873 (7) | 0.35394 (6) | 0.0373 (3) | |
O1' | 0.8473 (2) | 0.35291 (7) | 0.01239 (7) | 0.0391 (3) | |
O2 | 0.5218 (2) | 0.42635 (7) | 0.28348 (7) | 0.0378 (3) | |
O2' | 0.9776 (2) | 0.27666 (7) | −0.08522 (7) | 0.0368 (3) | |
O3 | 0.6423 (2) | 0.60016 (6) | 0.18325 (7) | 0.0356 (3) | |
O3' | 0.8457 (2) | 0.18825 (7) | 0.09531 (7) | 0.0375 (3) | |
O4 | 0.2300 (2) | 0.44081 (6) | −0.03259 (6) | 0.0326 (3) | |
O4' | 1.2655 (2) | 0.53480 (6) | 0.44361 (6) | 0.0313 (3) | |
O5' | 1.1091 (2) | 0.41374 (6) | 0.45713 (7) | 0.0325 (3) | |
O5 | 0.3751 (2) | 0.46786 (7) | 0.08859 (6) | 0.0319 (3) | |
O1W | 0.9806 (3) | 0.28785 (7) | 0.21789 (7) | 0.0358 (3) | |
O2W | 0.4974 (2) | 0.25205 (7) | 0.28943 (7) | 0.0350 (3) | |
N1 | 0.9008 (2) | 0.44502 (7) | 0.17545 (7) | 0.0259 (3) | |
H1A | 0.9068 | 0.3960 | 0.1921 | 0.039* | |
H1B | 1.0428 | 0.4540 | 0.1452 | 0.039* | |
H1C | 0.7448 | 0.4530 | 0.1483 | 0.039* | |
N1' | 0.5895 (3) | 0.17169 (7) | −0.06643 (7) | 0.0267 (3) | |
H1'1 | 0.5883 | 0.1873 | −0.1159 | 0.040* | |
H1'2 | 0.4431 | 0.1420 | −0.0586 | 0.040* | |
H1'3 | 0.7416 | 0.1445 | −0.0560 | 0.040* | |
C1 | 0.6765 (3) | 0.48003 (8) | 0.29580 (8) | 0.0248 (3) | |
C1' | 0.8258 (3) | 0.29214 (8) | −0.03325 (8) | 0.0257 (3) | |
C2 | 0.9143 (3) | 0.49845 (9) | 0.24344 (8) | 0.0248 (3) | |
H2 | 1.0874 | 0.4895 | 0.2726 | 0.030* | |
C2' | 0.5822 (3) | 0.24068 (8) | −0.01439 (8) | 0.0252 (3) | |
H2' | 0.4128 | 0.2697 | −0.0262 | 0.030* | |
C3' | 0.5839 (3) | 0.21712 (9) | 0.07053 (9) | 0.0323 (4) | |
H3'1 | 0.5372 | 0.2617 | 0.1021 | 0.039* | |
H3'2 | 0.4460 | 0.1773 | 0.0780 | 0.039* | |
C3 | 0.9044 (3) | 0.58255 (9) | 0.21666 (9) | 0.0320 (4) | |
H3A | 0.9424 | 0.6166 | 0.2607 | 0.038* | |
H3B | 1.0443 | 0.5913 | 0.1785 | 0.038* | |
C4 | 0.3861 (3) | 0.47357 (8) | 0.01697 (8) | 0.0223 (3) | |
C4' | 1.1078 (3) | 0.48458 (8) | 0.47118 (8) | 0.0221 (3) | |
H1' | 0.984 (6) | 0.3804 (17) | −0.0015 (16) | 0.077 (8)* | |
H1 | 0.516 (7) | 0.5199 (18) | 0.3820 (19) | 0.092 (9)* | |
H3 | 0.651 (5) | 0.5871 (15) | 0.1355 (15) | 0.058 (7)* | |
H3' | 0.852 (5) | 0.1413 (15) | 0.0831 (13) | 0.052 (6)* | |
H1W1 | 0.974 (5) | 0.2565 (15) | 0.1772 (15) | 0.058 (7)* | |
H2W1 | 0.844 (7) | 0.2749 (18) | 0.2448 (18) | 0.083 (9)* | |
H1W2 | 0.357 (6) | 0.2701 (17) | 0.2660 (17) | 0.075 (8)* | |
H2W2 | 0.459 (5) | 0.2031 (16) | 0.3000 (14) | 0.054 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0351 (6) | 0.0493 (7) | 0.0280 (6) | −0.0038 (5) | 0.0117 (5) | −0.0091 (5) |
O1' | 0.0393 (7) | 0.0278 (6) | 0.0511 (7) | −0.0133 (5) | 0.0154 (5) | −0.0099 (5) |
O2 | 0.0410 (6) | 0.0306 (6) | 0.0427 (7) | −0.0054 (5) | 0.0176 (5) | −0.0008 (5) |
O2' | 0.0341 (6) | 0.0388 (6) | 0.0380 (6) | −0.0122 (5) | 0.0104 (5) | −0.0055 (5) |
O3 | 0.0494 (7) | 0.0270 (6) | 0.0302 (6) | 0.0073 (5) | 0.0008 (5) | −0.0014 (4) |
O3' | 0.0482 (7) | 0.0292 (6) | 0.0347 (6) | 0.0019 (5) | −0.0065 (5) | −0.0043 (5) |
O4 | 0.0344 (6) | 0.0373 (6) | 0.0261 (5) | −0.0178 (5) | 0.0019 (4) | −0.0024 (4) |
O4' | 0.0321 (6) | 0.0255 (5) | 0.0373 (6) | −0.0005 (4) | 0.0164 (4) | −0.0017 (4) |
O5' | 0.0314 (6) | 0.0214 (5) | 0.0454 (6) | 0.0021 (4) | 0.0120 (5) | −0.0069 (4) |
O5 | 0.0306 (6) | 0.0434 (6) | 0.0219 (5) | −0.0101 (5) | 0.0055 (4) | 0.0013 (4) |
O1W | 0.0420 (7) | 0.0305 (6) | 0.0347 (6) | −0.0015 (5) | −0.0008 (5) | −0.0014 (5) |
O2W | 0.0385 (7) | 0.0276 (6) | 0.0386 (6) | −0.0040 (5) | −0.0029 (5) | 0.0031 (5) |
N1 | 0.0280 (6) | 0.0252 (6) | 0.0250 (6) | 0.0018 (5) | 0.0081 (5) | 0.0016 (5) |
N1' | 0.0278 (6) | 0.0249 (6) | 0.0276 (6) | −0.0065 (5) | 0.0013 (5) | 0.0006 (5) |
C1 | 0.0246 (7) | 0.0273 (7) | 0.0227 (7) | 0.0059 (6) | 0.0039 (5) | 0.0050 (5) |
C1' | 0.0241 (7) | 0.0225 (7) | 0.0304 (7) | −0.0016 (5) | −0.0012 (6) | 0.0031 (6) |
C2 | 0.0218 (7) | 0.0310 (7) | 0.0217 (7) | 0.0014 (5) | 0.0027 (5) | −0.0002 (6) |
C2' | 0.0211 (7) | 0.0212 (7) | 0.0333 (8) | −0.0022 (5) | 0.0021 (5) | −0.0013 (6) |
C3' | 0.0342 (8) | 0.0308 (8) | 0.0324 (8) | −0.0063 (6) | 0.0087 (6) | −0.0042 (6) |
C3 | 0.0367 (8) | 0.0289 (8) | 0.0308 (8) | −0.0074 (6) | 0.0063 (6) | −0.0034 (6) |
C4 | 0.0223 (7) | 0.0223 (7) | 0.0225 (7) | −0.0034 (5) | 0.0043 (5) | −0.0011 (5) |
C4' | 0.0215 (7) | 0.0219 (7) | 0.0230 (7) | 0.0027 (5) | 0.0035 (5) | −0.0014 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.3057 (19) | N1—H1A | 0.8900 |
O1—H1 | 0.89 (3) | N1—H1B | 0.8900 |
O1'—C1' | 1.3088 (19) | N1—H1C | 0.8900 |
O1'—H1' | 0.86 (3) | N1'—C2' | 1.4865 (19) |
O2—C1 | 1.2064 (19) | N1'—H1'1 | 0.8900 |
O2'—C1' | 1.2051 (18) | N1'—H1'2 | 0.8900 |
O3—C3 | 1.417 (2) | N1'—H1'3 | 0.8900 |
O3—H3 | 0.85 (3) | C1—C2 | 1.5200 (19) |
O3'—C3' | 1.421 (2) | C1'—C2' | 1.5224 (19) |
O3'—H3' | 0.84 (3) | C2—C3 | 1.518 (2) |
O4—C4 | 1.2575 (18) | C2—H2 | 0.9800 |
O4'—C4' | 1.2572 (17) | C2'—C3' | 1.513 (2) |
O5'—C4' | 1.2419 (18) | C2'—H2' | 0.9800 |
O5—C4 | 1.2365 (17) | C3'—H3'1 | 0.9700 |
O1W—H1W1 | 0.88 (3) | C3'—H3'2 | 0.9700 |
O1W—H2W1 | 0.85 (3) | C3—H3A | 0.9700 |
O2W—H1W2 | 0.84 (3) | C3—H3B | 0.9700 |
O2W—H2W2 | 0.88 (3) | C4—C4i | 1.560 (2) |
N1—C2 | 1.4857 (18) | C4'—C4'ii | 1.557 (2) |
| | | |
C1—O1—H1 | 111 (2) | N1—C2—H2 | 108.9 |
C1'—O1'—H1' | 108.9 (19) | C3—C2—H2 | 108.9 |
C3—O3—H3 | 105.2 (16) | C1—C2—H2 | 108.9 |
C3'—O3'—H3' | 107.7 (15) | N1'—C2'—C3' | 111.48 (12) |
H1W1—O1W—H2W1 | 105 (3) | N1'—C2'—C1' | 107.67 (11) |
H1W2—O2W—H2W2 | 106 (2) | C3'—C2'—C1' | 112.22 (12) |
C2—N1—H1A | 109.5 | N1'—C2'—H2' | 108.5 |
C2—N1—H1B | 109.5 | C3'—C2'—H2' | 108.5 |
H1A—N1—H1B | 109.5 | C1'—C2'—H2' | 108.5 |
C2—N1—H1C | 109.5 | O3'—C3'—C2' | 111.21 (12) |
H1A—N1—H1C | 109.5 | O3'—C3'—H3'1 | 109.4 |
H1B—N1—H1C | 109.5 | C2'—C3'—H3'1 | 109.4 |
C2'—N1'—H1'1 | 109.5 | O3'—C3'—H3'2 | 109.4 |
C2'—N1'—H1'2 | 109.5 | C2'—C3'—H3'2 | 109.4 |
H1'1—N1'—H1'2 | 109.5 | H3'1—C3'—H3'2 | 108.0 |
C2'—N1'—H1'3 | 109.5 | O3—C3—C2 | 110.28 (12) |
H1'1—N1'—H1'3 | 109.5 | O3—C3—H3A | 109.6 |
H1'2—N1'—H1'3 | 109.5 | C2—C3—H3A | 109.6 |
O2—C1—O1 | 125.67 (13) | O3—C3—H3B | 109.6 |
O2—C1—C2 | 122.57 (13) | C2—C3—H3B | 109.6 |
O1—C1—C2 | 111.76 (12) | H3A—C3—H3B | 108.1 |
O2'—C1'—O1' | 125.46 (13) | O5—C4—O4 | 126.48 (12) |
O2'—C1'—C2' | 121.84 (13) | O5—C4—C4i | 118.04 (15) |
O1'—C1'—C2' | 112.70 (12) | O4—C4—C4i | 115.49 (14) |
N1—C2—C3 | 110.55 (11) | O5'—C4'—O4' | 126.47 (12) |
N1—C2—C1 | 108.60 (12) | O5'—C4'—C4'ii | 117.70 (15) |
C3—C2—C1 | 111.09 (12) | O4'—C4'—C4'ii | 115.83 (14) |
| | | |
O2—C1—C2—N1 | 4.77 (19) | O2'—C1'—C2'—C3' | 126.59 (15) |
O1—C1—C2—N1 | −175.35 (11) | O1'—C1'—C2'—C3' | −53.56 (17) |
O2—C1—C2—C3 | 126.55 (15) | N1'—C2'—C3'—O3' | 71.98 (15) |
O1—C1—C2—C3 | −53.56 (16) | C1'—C2'—C3'—O3' | −48.90 (16) |
O2'—C1'—C2'—N1' | 3.55 (19) | N1—C2—C3—O3 | 68.19 (15) |
O1'—C1'—C2'—N1' | −176.60 (12) | C1—C2—C3—O3 | −52.45 (16) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1W | 0.89 | 1.94 | 2.823 (2) | 170 |
N1—H1B···O5iii | 0.89 | 1.93 | 2.8129 (16) | 174 |
N1—H1C···O5 | 0.89 | 2.06 | 2.9507 (18) | 177 |
N1′—H1′1···O2Wiv | 0.89 | 1.97 | 2.8254 (18) | 160 |
N1′—H1′2···O5′v | 0.89 | 1.91 | 2.8015 (16) | 175 |
N1′—H1′3···O5′iv | 0.89 | 2.06 | 2.9431 (17) | 174 |
O1′—H1′···O4iii | 0.86 (3) | 1.68 (3) | 2.5374 (15) | 174 (3) |
O1—H1···O4′vi | 0.89 (3) | 1.66 (3) | 2.5158 (15) | 160 (3) |
O3—H3···O4i | 0.85 (3) | 1.94 (3) | 2.7696 (17) | 166 (2) |
O3′—H3′···O4′vii | 0.84 (3) | 1.97 (3) | 2.7718 (19) | 161 (2) |
O1W—H1W1···O3′ | 0.88 (3) | 1.92 (3) | 2.7778 (18) | 163 (2) |
O1W—H2W1···O2W | 0.85 (3) | 1.91 (3) | 2.7552 (19) | 170 (3) |
O2W—H1W2···O1Wvi | 0.84 (3) | 2.01 (3) | 2.8352 (18) | 166 (3) |
O2W—H2W2···O3viii | 0.88 (3) | 1.86 (3) | 2.7432 (19) | 176 (2) |
C2—H2···O2iii | 0.98 | 2.38 | 3.2616 (19) | 149 |
C2′—H2′···O2′vi | 0.98 | 2.32 | 3.2120 (19) | 150 |
Symmetry codes: (i) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) x, −y+1/2, z−1/2; (v) x−1, −y+1/2, z−1/2; (vi) x−1, y, z; (vii) −x+2, y−1/2, −z+1/2; (viii) −x+1, y−1/2, −z+1/2. |