Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100020370/vj1124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020370/vj1124Isup2.hkl |
CCDC reference: 163910
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS93 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C5H10NO2+·C4H5O6− | F(000) = 284 |
Mr = 267.24 | Dx = 1.551 Mg m−3 Dm = 1.55 Mg m−3 Dm measured by flotation |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
a = 5.007 (1) Å | Cell parameters from 25 reflections |
b = 17.676 (3) Å | θ = 16–26° |
c = 6.523 (1) Å | µ = 1.21 mm−1 |
β = 100.40 (2)° | T = 293 K |
V = 567.8 (2) Å3 | Needles, colourless |
Z = 2 | 0.42 × 0.35 × 0.21 mm |
Enraf-Nonius CAD-4 diffractometer | 968 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 67.9°, θmin = 5.0° |
ω/2θ scans | h = 0→6 |
Absorption correction: ψ-scan (North et al., 1968) | k = 0→17 |
Tmin = 0.540, Tmax = 0.734 | l = −7→6 |
1077 measured reflections | 2 standard reflections every 200 reflections |
974 independent reflections | intensity decay: 0.1% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0513P)2 + 0.1468P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.16 e Å−3 |
974 reflections | Δρmin = −0.18 e Å−3 |
178 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.060 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.1 (3) |
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 0 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 | Occ. (<1) | |
O1 | 0.8186 (4) | 0.47409 (14) | 0.7398 (4) | 0.0494 (6) | |
H1 | 0.9601 | 0.4948 | 0.7945 | 0.074* | |
O2 | 1.0870 (4) | 0.37594 (16) | 0.7105 (4) | 0.0626 (8) | |
O3 | 0.9331 (3) | 0.60674 (11) | 0.4467 (3) | 0.0341 (4) | |
H11 | 1.0595 | 0.6186 | 0.5395 | 0.051* | |
O4 | 0.7627 (3) | 0.71715 (10) | 0.5289 (3) | 0.0313 (4) | |
O5 | 0.3369 (3) | 0.70372 (10) | 0.2185 (3) | 0.0293 (4) | |
H13 | 0.1876 | 0.6900 | 0.1563 | 0.044* | |
O6 | 0.7794 (3) | 0.67500 (11) | −0.0068 (3) | 0.0323 (5) | |
H15 | 0.7437 | 0.6800 | −0.1338 | 0.048* | |
O7 | 0.3422 (4) | 0.63018 (12) | −0.2814 (3) | 0.0364 (5) | |
O8 | 0.2251 (4) | 0.54422 (12) | −0.0614 (3) | 0.0412 (5) | |
N1 | 0.7154 (4) | 0.30306 (13) | 0.4339 (3) | 0.0333 (5) | |
H9 | 0.8876 | 0.2911 | 0.4906 | 0.040* | |
H10 | 0.6082 | 0.2636 | 0.4513 | 0.040* | |
C1 | 0.8727 (5) | 0.40807 (17) | 0.6720 (4) | 0.0335 (6) | |
C2 | 0.6270 (5) | 0.37223 (16) | 0.5379 (4) | 0.0320 (6) | |
H2 | 0.4946 | 0.3580 | 0.6249 | 0.038* | |
C3 | 0.4903 (7) | 0.4213 (2) | 0.3576 (5) | 0.0559 (9) | |
H3 | 0.2993 | 0.4087 | 0.3182 | 0.067* | |
H4 | 0.5075 | 0.4745 | 0.3933 | 0.067* | |
C4 | 0.6384 (12) | 0.4030 (3) | 0.1897 (8) | 0.0509 (17) | 0.711 (13) |
H5 | 0.8067 | 0.4314 | 0.2060 | 0.061* | 0.711 (13) |
H6 | 0.5295 | 0.4150 | 0.0551 | 0.061* | 0.711 (13) |
C4' | 0.468 (3) | 0.3750 (7) | 0.1615 (17) | 0.049 (4) | 0.289 (13) |
H5' | 0.2944 | 0.3490 | 0.1313 | 0.059* | 0.289 (13) |
H6' | 0.4868 | 0.4067 | 0.0436 | 0.059* | 0.289 (13) |
C5 | 0.6948 (8) | 0.3199 (2) | 0.2070 (5) | 0.0480 (8) | |
H7 | 0.8632 | 0.3078 | 0.1607 | 0.058* | |
H8 | 0.5484 | 0.2913 | 0.1244 | 0.058* | |
C6 | 0.7511 (5) | 0.65955 (14) | 0.4242 (3) | 0.0240 (5) | |
C7 | 0.5137 (4) | 0.64074 (14) | 0.2524 (3) | 0.0231 (5) | |
H12 | 0.4142 | 0.5982 | 0.2990 | 0.028* | |
C8 | 0.6173 (5) | 0.61642 (14) | 0.0548 (3) | 0.0245 (5) | |
H14 | 0.7310 | 0.5714 | 0.0875 | 0.029* | |
C9 | 0.3727 (5) | 0.59527 (14) | −0.1118 (4) | 0.0261 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0382 (10) | 0.0446 (14) | 0.0639 (15) | −0.0046 (10) | 0.0054 (10) | −0.0201 (11) |
O2 | 0.0307 (10) | 0.0664 (17) | 0.0847 (19) | 0.0062 (11) | −0.0059 (11) | −0.0291 (15) |
O3 | 0.0312 (9) | 0.0383 (11) | 0.0273 (9) | 0.0072 (8) | −0.0098 (7) | −0.0052 (8) |
O4 | 0.0313 (8) | 0.0329 (11) | 0.0273 (9) | −0.0030 (7) | −0.0009 (7) | −0.0081 (7) |
O5 | 0.0254 (8) | 0.0306 (10) | 0.0291 (9) | 0.0044 (7) | −0.0024 (7) | −0.0028 (7) |
O6 | 0.0281 (8) | 0.0440 (11) | 0.0233 (8) | −0.0089 (8) | 0.0008 (6) | 0.0010 (8) |
O7 | 0.0311 (9) | 0.0501 (13) | 0.0242 (10) | −0.0035 (8) | −0.0056 (7) | 0.0033 (8) |
O8 | 0.0445 (11) | 0.0392 (12) | 0.0359 (11) | −0.0141 (9) | −0.0034 (8) | −0.0027 (8) |
N1 | 0.0336 (10) | 0.0260 (13) | 0.0394 (12) | −0.0031 (9) | 0.0041 (9) | 0.0015 (9) |
C1 | 0.0279 (12) | 0.0396 (16) | 0.0343 (14) | −0.0026 (11) | 0.0091 (10) | −0.0029 (12) |
C2 | 0.0271 (11) | 0.0308 (15) | 0.0377 (15) | 0.0014 (11) | 0.0048 (10) | −0.0014 (11) |
C3 | 0.0598 (18) | 0.041 (2) | 0.059 (2) | 0.0145 (15) | −0.0113 (15) | −0.0005 (15) |
C4 | 0.057 (4) | 0.046 (3) | 0.044 (3) | −0.006 (3) | −0.006 (2) | 0.017 (2) |
C4' | 0.063 (9) | 0.036 (7) | 0.039 (7) | −0.006 (6) | −0.016 (5) | 0.004 (5) |
C5 | 0.060 (2) | 0.047 (2) | 0.0356 (16) | −0.0045 (15) | 0.0050 (14) | −0.0038 (13) |
C6 | 0.0247 (10) | 0.0272 (14) | 0.0192 (11) | −0.0030 (9) | 0.0017 (8) | 0.0021 (9) |
C7 | 0.0224 (10) | 0.0254 (12) | 0.0198 (12) | −0.0016 (9) | −0.0004 (8) | −0.0006 (9) |
C8 | 0.0241 (10) | 0.0257 (13) | 0.0216 (12) | 0.0008 (9) | −0.0013 (9) | −0.0017 (9) |
C9 | 0.0246 (11) | 0.0269 (14) | 0.0250 (13) | 0.0001 (10) | 0.0002 (9) | −0.0061 (10) |
O1—C1 | 1.294 (4) | C2—H2 | 0.9800 |
O1—H1 | 0.8200 | C3—C4 | 1.465 (6) |
O2—C1 | 1.200 (4) | C3—C4' | 1.505 (12) |
O3—C6 | 1.294 (3) | C3—H3 | 0.9700 |
O3—H11 | 0.8200 | C3—H4 | 0.9700 |
O4—C6 | 1.221 (3) | C4—C5 | 1.495 (6) |
O5—C7 | 1.415 (3) | C4—H5 | 0.9700 |
O5—H13 | 0.8200 | C4—H6 | 0.9700 |
O6—C8 | 1.418 (3) | C4'—C5 | 1.484 (13) |
O6—H15 | 0.8200 | C4'—H5' | 0.9700 |
O7—C9 | 1.252 (3) | C4'—H6' | 0.9700 |
O8—C9 | 1.248 (3) | C5—H7 | 0.9700 |
N1—C5 | 1.495 (4) | C5—H8 | 0.9700 |
N1—C2 | 1.503 (3) | C6—C7 | 1.516 (3) |
N1—H9 | 0.9000 | C7—C8 | 1.535 (3) |
N1—H10 | 0.9000 | C7—H12 | 0.9800 |
C1—C2 | 1.513 (4) | C8—C9 | 1.530 (3) |
C2—C3 | 1.521 (4) | C8—H14 | 0.9800 |
C1—O1—H1 | 109.5 | C5—C4'—C3 | 104.4 (7) |
C6—O3—H11 | 109.5 | C5—C4'—H5' | 110.9 |
C7—O5—H13 | 109.5 | C3—C4'—H5' | 110.9 |
C8—O6—H15 | 109.5 | C5—C4'—H6' | 110.9 |
C5—N1—C2 | 108.1 (2) | C3—C4'—H6' | 110.9 |
C5—N1—H9 | 110.1 | H5'—C4'—H6' | 108.9 |
C2—N1—H9 | 110.1 | C4'—C5—C4 | 38.2 (5) |
C5—N1—H10 | 110.1 | C4'—C5—N1 | 104.0 (5) |
C2—N1—H10 | 110.1 | C4—C5—N1 | 104.4 (3) |
H9—N1—H10 | 108.4 | C4'—C5—H7 | 139.4 |
O2—C1—O1 | 126.1 (3) | C4—C5—H7 | 110.9 |
O2—C1—C2 | 121.7 (3) | N1—C5—H7 | 110.9 |
O1—C1—C2 | 112.1 (2) | C4'—C5—H8 | 75.9 |
N1—C2—C1 | 109.1 (2) | C4—C5—H8 | 110.9 |
N1—C2—C3 | 104.0 (2) | N1—C5—H8 | 110.9 |
C1—C2—C3 | 114.4 (3) | H7—C5—H8 | 108.9 |
N1—C2—H2 | 109.7 | O4—C6—O3 | 125.2 (2) |
C1—C2—H2 | 109.7 | O4—C6—C7 | 123.2 (2) |
C3—C2—H2 | 109.7 | O3—C6—C7 | 111.6 (2) |
C4—C3—C4' | 38.3 (5) | O5—C7—C6 | 109.15 (19) |
C4—C3—C2 | 103.6 (3) | O5—C7—C8 | 112.70 (19) |
C4'—C3—C2 | 107.5 (5) | C6—C7—C8 | 110.09 (17) |
C4—C3—H3 | 111.1 | O5—C7—H12 | 108.3 |
C4'—C3—H3 | 74.4 | C6—C7—H12 | 108.3 |
C2—C3—H3 | 111.1 | C8—C7—H12 | 108.3 |
C4—C3—H4 | 111.1 | O6—C8—C9 | 113.78 (18) |
C4'—C3—H4 | 136.2 | O6—C8—C7 | 109.32 (19) |
C2—C3—H4 | 111.1 | C9—C8—C7 | 108.45 (17) |
H3—C3—H4 | 109.0 | O6—C8—H14 | 108.4 |
C3—C4—C5 | 105.9 (4) | C9—C8—H14 | 108.4 |
C3—C4—H5 | 110.5 | C7—C8—H14 | 108.4 |
C5—C4—H5 | 110.5 | O8—C9—O7 | 127.3 (2) |
C3—C4—H6 | 110.5 | O8—C9—C8 | 115.2 (2) |
C5—C4—H6 | 110.5 | O7—C9—C8 | 117.5 (2) |
H5—C4—H6 | 108.7 | ||
C5—N1—C2—C1 | −108.9 (3) | C3—C4—C5—C4' | 65.0 (8) |
C5—N1—C2—C3 | 13.7 (3) | C3—C4—C5—N1 | −29.5 (5) |
O2—C1—C2—N1 | −11.8 (4) | C2—N1—C5—C4' | −30.4 (7) |
O1—C1—C2—N1 | 169.8 (2) | C2—N1—C5—C4 | 9.0 (4) |
O2—C1—C2—C3 | −127.8 (3) | O4—C6—C7—O5 | 7.8 (3) |
O1—C1—C2—C3 | 53.8 (3) | O3—C6—C7—O5 | −173.38 (18) |
N1—C2—C3—C4 | −31.6 (4) | O4—C6—C7—C8 | 132.0 (2) |
C1—C2—C3—C4 | 87.4 (4) | O3—C6—C7—C8 | −49.2 (3) |
N1—C2—C3—C4' | 8.1 (7) | O5—C7—C8—O6 | 64.7 (2) |
C1—C2—C3—C4' | 127.0 (7) | C6—C7—C8—O6 | −57.4 (2) |
C4'—C3—C4—C5 | −63.1 (8) | O5—C7—C8—C9 | −59.9 (2) |
C2—C3—C4—C5 | 38.2 (5) | C6—C7—C8—C9 | 178.0 (2) |
C4—C3—C4'—C5 | 63.0 (8) | O6—C8—C9—O8 | −179.5 (2) |
C2—C3—C4'—C5 | −26.7 (10) | C7—C8—C9—O8 | −57.6 (3) |
C3—C4'—C5—C4 | −61.1 (8) | O6—C8—C9—O7 | 0.6 (3) |
C3—C4'—C5—N1 | 34.5 (9) | C7—C8—C9—O7 | 122.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O8i | 0.82 | 1.72 | 2.531 (3) | 170 |
N1—H9···O4ii | 0.90 | 2.21 | 2.994 (3) | 146 |
N1—H10···O4iii | 0.90 | 2.06 | 2.881 (3) | 152 |
O3—H11···O7i | 0.82 | 1.68 | 2.490 (2) | 171 |
O5—H13···O6iv | 0.82 | 2.14 | 2.954 (2) | 170 |
O6—H15···O4v | 0.82 | 2.31 | 3.105 (3) | 162 |
C2—H2···O2iv | 0.98 | 2.23 | 3.112 (3) | 149 |
Symmetry codes: (i) x+1, y, z+1; (ii) −x+2, y−1/2, −z+1; (iii) −x+1, y−1/2, −z+1; (iv) x−1, y, z; (v) x, y, z−1. |