Supporting information
Crystallographic Information File (CIF) | |
Structure factor file (CIF format) |
CCDC reference: 134771
Data collection: KM4; cell refinement: KM4; data reduction: DATARED; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SIEMENS STEREOCHEMICAL WORKSTATION.
C5H9NO5·H2O | Dx = 1.553 Mg m−3 Dm = 1.533 Mg m−3 Dm measured by flotation in KI |
Mr = 181.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 36 reflections |
a = 7.301 (1) Å | θ = 8.4–14.8° |
b = 7.658 (2) Å | µ = 0.14 mm−1 |
c = 13.855 (3) Å | T = 293 K |
V = 774.6 (3) Å3 | Prism, transparent |
Z = 4 | 0.6 × 0.25 × 0.2 mm |
F(000) = 384 |
KM-4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 28.1°, θmin = 2.9° |
Graphite monochromator | h = −9→9 |
θ–2θ scans | k = 0→10 |
2066 measured reflections | l = 0→18 |
1875 independent reflections | 2 standard reflections every 100 reflections |
1485 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.031 | Calculated w = 1/[σ2(Fo2) + (0.0445P)2 + 0.0586P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.18 e Å−3 |
1874 reflections | Δρmin = −0.17 e Å−3 |
129 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
0 restraints | Absolute structure parameter: −0.70 (130) |
Primary atom site location: structure-invariant direct methods |
C5H9NO5·H2O | V = 774.6 (3) Å3 |
Mr = 181.15 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.301 (1) Å | µ = 0.14 mm−1 |
b = 7.658 (2) Å | T = 293 K |
c = 13.855 (3) Å | 0.6 × 0.25 × 0.2 mm |
KM-4 diffractometer | Rint = 0.021 |
2066 measured reflections | 2 standard reflections every 100 reflections |
1875 independent reflections | intensity decay: none |
1485 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.084 | Δρmax = 0.18 e Å−3 |
S = 1.07 | Δρmin = −0.17 e Å−3 |
1874 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
129 parameters | Absolute structure parameter: −0.70 (130) |
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 1 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2930 (2) | 0.4182 (2) | 0.41106 (12) | 0.0259 (3) | |
C2 | 0.5003 (2) | 0.4140 (2) | 0.40321 (11) | 0.0228 (3) | |
H2 | 0.5490 (2) | 0.3583 (2) | 0.45972 (11) | 0.027* | |
C3 | 0.5602 (2) | 0.3101 (2) | 0.31528 (12) | 0.0239 (3) | |
H3 | 0.5291 (2) | 0.1897 (2) | 0.32537 (12) | 0.029* | |
C4 | 0.7664 (2) | 0.3249 (2) | 0.30344 (12) | 0.0244 (3) | |
C40 | 1.0165 (3) | 0.3828 (3) | 0.19197 (15) | 0.0399 (5) | |
H401 | 1.0819 (3) | 0.4648 (3) | 0.23146 (15) | 0.048* | |
H402 | 1.0285 (3) | 0.4179 (3) | 0.12574 (15) | 0.048* | |
H403 | 1.0652 (3) | 0.2675 (3) | 0.20078 (15) | 0.048* | |
N4 | 0.8254 (2) | 0.3773 (2) | 0.21926 (10) | 0.0326 (4) | |
H4 | 0.7420 (2) | 0.4135 (2) | 0.17582 (10) | 0.039* | |
O1 | 0.2101 (2) | 0.5480 (2) | 0.43369 (13) | 0.0463 (4) | |
O2 | 0.5651 (2) | 0.5878 (2) | 0.40023 (9) | 0.0289 (3) | |
H2O | 0.668 (4) | 0.601 (4) | 0.443 (2) | 0.070 (8)* | |
O3 | 0.4658 (2) | 0.3721 (2) | 0.23251 (9) | 0.0321 (3) | |
H3O | 0.444 (4) | 0.284 (4) | 0.193 (2) | 0.075 (9)* | |
O4 | 0.8662 (2) | 0.2838 (2) | 0.37232 (9) | 0.0324 (3) | |
O10 | 0.2160 (2) | 0.2688 (2) | 0.39214 (9) | 0.0303 (3) | |
H10 | 0.088 (5) | 0.279 (4) | 0.377 (3) | 0.088 (10)* | |
O(W) | 0.1486 (2) | 0.1173 (2) | 0.98452 (10) | 0.0358 (3) | |
H1W | 0.047 (4) | 0.086 (4) | 1.005 (2) | 0.056 (8)* | |
H2W | 0.138 (5) | 0.230 (5) | 0.969 (3) | 0.098 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0232 (8) | 0.0306 (9) | 0.0240 (8) | 0.0014 (7) | −0.0001 (6) | 0.0001 (7) |
C2 | 0.0219 (7) | 0.0246 (8) | 0.0218 (7) | 0.0011 (6) | −0.0025 (6) | 0.0000 (6) |
C3 | 0.0192 (7) | 0.0253 (8) | 0.0270 (8) | 0.0009 (6) | −0.0024 (7) | −0.0023 (6) |
C4 | 0.0208 (8) | 0.0232 (8) | 0.0294 (8) | 0.0009 (6) | 0.0012 (6) | −0.0044 (7) |
C40 | 0.0295 (9) | 0.0530 (12) | 0.0371 (10) | −0.0018 (9) | 0.0075 (8) | 0.0070 (9) |
N4 | 0.0238 (8) | 0.0443 (9) | 0.0296 (8) | 0.0010 (7) | 0.0000 (6) | 0.0033 (7) |
O1 | 0.0257 (7) | 0.0388 (8) | 0.0744 (11) | 0.0029 (6) | 0.0065 (7) | −0.0184 (7) |
O2 | 0.0253 (6) | 0.0257 (6) | 0.0358 (7) | −0.0029 (5) | −0.0058 (5) | −0.0049 (5) |
O3 | 0.0278 (7) | 0.0423 (8) | 0.0262 (6) | 0.0034 (6) | −0.0062 (5) | −0.0059 (6) |
O4 | 0.0203 (6) | 0.0462 (7) | 0.0309 (6) | 0.0019 (6) | −0.0017 (5) | 0.0048 (5) |
O10 | 0.0219 (6) | 0.0306 (6) | 0.0384 (7) | −0.0012 (5) | −0.0007 (5) | 0.0013 (5) |
O(W) | 0.0307 (7) | 0.0369 (8) | 0.0398 (7) | 0.0012 (7) | −0.0033 (6) | 0.0097 (6) |
C1—O1 | 1.205 (2) | C40—N4 | 1.446 (2) |
C1—O10 | 1.302 (2) | C40—H401 | 0.96 |
C1—C2 | 1.518 (2) | C40—H402 | 0.96 |
C2—O2 | 1.413 (2) | C40—H403 | 0.96 |
C2—C3 | 1.519 (2) | N4—H4 | 0.90 |
C2—H2 | 0.96 | O2—H2O | 0.96 (3) |
C3—O3 | 1.419 (2) | O3—H3O | 0.88 (3) |
C3—C4 | 1.519 (2) | O10—H10 | 0.96 (3) |
C3—H3 | 0.96 | O(W)—H1W | 0.83 (3) |
C4—O4 | 1.241 (2) | O(W)—H2W | 0.89 (4) |
C4—N4 | 1.307 (2) | ||
O1—C1—O10 | 124.1 (2) | O4—C4—C3 | 118.7 (2) |
O1—C1—C2 | 122.5 (2) | N4—C4—C3 | 116.5 (2) |
O10—C1—C2 | 113.44 (14) | N4—C40—H401 | 110.50 (11) |
O2—C2—C1 | 108.42 (13) | N4—C40—H402 | 110.24 (10) |
O2—C2—C3 | 111.93 (14) | H401—C40—H402 | 108.5 |
C1—C2—C3 | 110.82 (13) | N4—C40—H403 | 107.29 (12) |
O2—C2—H2 | 108.58 (8) | H401—C40—H403 | 110.2 |
C1—C2—H2 | 108.67 (9) | H402—C40—H403 | 110.2 |
C3—C2—H2 | 108.35 (9) | C4—N4—C40 | 124.1 (2) |
O3—C3—C4 | 111.66 (14) | C4—N4—H4 | 117.94 (10) |
O3—C3—C2 | 109.47 (13) | C40—N4—H4 | 117.97 (10) |
C4—C3—C2 | 109.44 (14) | C2—O2—H2O | 109.8 (19) |
O3—C3—H3 | 108.89 (9) | C3—O3—H3O | 110 (2) |
C4—C3—H3 | 108.78 (9) | C1—O10—H10 | 113 (2) |
C2—C3—H3 | 108.54 (9) | H1W—O(W)—H2W | 106 (3) |
O4—C4—N4 | 124.8 (2) | ||
O1—C1—C2—O2 | −15.7 (2) | C1—C2—C3—C4 | 173.93 (13) |
O10—C1—C2—O2 | 165.06 (13) | O3—C3—C4—O4 | 176.33 (14) |
O1—C1—C2—C3 | −138.9 (2) | C2—C3—C4—O4 | 55.0 (2) |
O10—C1—C2—C3 | 41.8 (2) | O3—C3—C4—N4 | −5.1 (2) |
O2—C2—C3—O3 | −69.9 (2) | C2—C3—C4—N4 | −126.4 (2) |
C1—C2—C3—O3 | 51.3 (2) | O4—C4—N4—C40 | 4.7 (3) |
O2—C2—C3—C4 | 52.8 (2) | C3—C4—N4—C40 | −173.8 (2) |
Experimental details
Crystal data | |
Chemical formula | C5H9NO5·H2O |
Mr | 181.15 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.301 (1), 7.658 (2), 13.855 (3) |
V (Å3) | 774.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.6 × 0.25 × 0.2 |
Data collection | |
Diffractometer | KM-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2066, 1875, 1485 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.662 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.084, 1.07 |
No. of reflections | 1874 |
No. of parameters | 129 |
Δρmax, Δρmin (e Å−3) | 0.18, −0.17 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.70 (130) |
Computer programs: KM4, DATARED, SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), SIEMENS STEREOCHEMICAL WORKSTATION.
O1—C1—C2—O2 | −15.7 (2) | C1—C2—C3—C4 | 173.93 (13) |
O10—C1—C2—O2 | 165.06 (13) | O3—C3—C4—O4 | 176.33 (14) |
O1—C1—C2—C3 | −138.9 (2) | C2—C3—C4—O4 | 55.0 (2) |
O10—C1—C2—C3 | 41.8 (2) | O3—C3—C4—N4 | −5.1 (2) |
O2—C2—C3—O3 | −69.9 (2) | C2—C3—C4—N4 | −126.4 (2) |
C1—C2—C3—O3 | 51.3 (2) | O4—C4—N4—C40 | 4.7 (3) |
O2—C2—C3—C4 | 52.8 (2) | C3—C4—N4—C40 | −173.8 (2) |