The title compound, C
14H
19NO
10, forms strong hydrogen bonds
via amido groups in the [100] direction; soft C—H
O bonds also act to give chains along both [100] and [001], which combine to form a two-dimensional layer.
Supporting information
CCDC reference: 183810
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.093
- Data-to-parameter ratio = 9.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.764 0.992
Tmin' and Tmax expected: 0.969 0.976
RR' = 0.775
Please check that your absorption correction is appropriate.
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 2217
Count of symmetry unique reflns 2232
Completeness (_total/calc) 99.33%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEPIII for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2000) and SHELXL97.
1,2,3,4-tetra-acetyl-alpha-
D-glucuronamide
top
Crystal data top
C14H19NO10 | Dx = 1.430 Mg m−3 |
Mr = 361.30 | Melting point = 365–366 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5811 (2) Å | Cell parameters from 9393 reflections |
b = 16.9550 (6) Å | θ = 2.9–27.5° |
c = 17.7323 (6) Å | µ = 0.12 mm−1 |
V = 1677.96 (10) Å3 | T = 120 K |
Z = 4 | Block, colourless |
F(000) = 760 | 0.25 × 0.20 × 0.20 mm |
Data collection top
Nonius KappaCCD detector diffractometer | 2217 independent reflections |
Radiation source: fine-focus sealed tube | 1926 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
φ and ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | h = −7→7 |
Tmin = 0.764, Tmax = 0.992 | k = −19→21 |
10467 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0584P)2 + 0.1398P] where P = (Fo2 + 2Fc2)/3 |
2217 reflections | (Δ/σ)max = 0.001 |
238 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | |
O5 | 0.0564 (3) | 1.04864 (8) | 0.14352 (8) | 0.0195 (3) | |
C1 | 0.1298 (4) | 0.98603 (12) | 0.19046 (11) | 0.0198 (4) | |
H1 | −0.0111 | 0.9664 | 0.2198 | 0.024* | |
O1 | 0.3096 (3) | 1.01304 (9) | 0.24170 (8) | 0.0220 (3) | |
C7 | 0.2257 (4) | 1.05514 (13) | 0.30218 (12) | 0.0245 (5) | |
O7 | 0.0160 (3) | 1.06349 (10) | 0.31475 (9) | 0.0323 (4) | |
C8 | 0.4264 (5) | 1.08823 (15) | 0.34718 (13) | 0.0324 (6) | |
H8A | 0.3804 | 1.0902 | 0.4005 | 0.049* | |
H8B | 0.4630 | 1.1416 | 0.3294 | 0.049* | |
H8C | 0.5683 | 1.0547 | 0.3413 | 0.049* | |
C2 | 0.2334 (4) | 0.91835 (12) | 0.14366 (11) | 0.0193 (4) | |
H2 | 0.0988 | 0.8900 | 0.1181 | 0.023* | |
O2 | 0.3600 (3) | 0.86324 (9) | 0.19146 (8) | 0.0238 (3) | |
C9 | 0.2227 (5) | 0.80986 (13) | 0.22860 (12) | 0.0255 (5) | |
O8 | 0.0088 (3) | 0.80580 (11) | 0.22082 (9) | 0.0351 (4) | |
C10 | 0.3728 (5) | 0.76043 (14) | 0.28026 (13) | 0.0355 (6) | |
H10A | 0.3062 | 0.7070 | 0.2829 | 0.053* | |
H10B | 0.3734 | 0.7839 | 0.3308 | 0.053* | |
H10C | 0.5372 | 0.7580 | 0.2610 | 0.053* | |
C3 | 0.4123 (4) | 0.94516 (12) | 0.08413 (11) | 0.0181 (4) | |
H3 | 0.5723 | 0.9555 | 0.1075 | 0.022* | |
O3 | 0.4277 (3) | 0.88084 (8) | 0.03011 (8) | 0.0200 (3) | |
C11 | 0.6455 (4) | 0.86169 (12) | 0.00183 (11) | 0.0200 (4) | |
O9 | 0.8293 (3) | 0.89291 (10) | 0.02056 (9) | 0.0291 (4) | |
C12 | 0.6241 (5) | 0.79711 (13) | −0.05536 (12) | 0.0268 (5) | |
H12A | 0.5521 | 0.7505 | −0.0318 | 0.040* | |
H12B | 0.7835 | 0.7837 | −0.0746 | 0.040* | |
H12C | 0.5225 | 0.8149 | −0.0971 | 0.040* | |
C4 | 0.3236 (4) | 1.01771 (11) | 0.04228 (11) | 0.0175 (4) | |
H4 | 0.1838 | 1.0037 | 0.0097 | 0.021* | |
O4 | 0.5189 (3) | 1.04521 (8) | −0.00333 (7) | 0.0183 (3) | |
C13 | 0.4614 (4) | 1.07868 (13) | −0.07107 (11) | 0.0192 (4) | |
O10 | 0.2600 (3) | 1.08249 (9) | −0.09427 (8) | 0.0251 (4) | |
C14 | 0.6795 (4) | 1.10887 (14) | −0.11025 (12) | 0.0248 (5) | |
H14A | 0.7023 | 1.1647 | −0.0979 | 0.037* | |
H14B | 0.6597 | 1.1030 | −0.1649 | 0.037* | |
H14C | 0.8198 | 1.0787 | −0.0937 | 0.037* | |
C5 | 0.2503 (4) | 1.08038 (12) | 0.10023 (11) | 0.0185 (4) | |
H5 | 0.3889 | 1.0909 | 0.1346 | 0.022* | |
C6 | 0.1751 (4) | 1.15714 (12) | 0.06316 (12) | 0.0202 (4) | |
N1 | −0.0594 (4) | 1.16937 (12) | 0.05512 (11) | 0.0240 (4) | |
H1A | −0.169 (5) | 1.1319 (17) | 0.0703 (16) | 0.041 (8)* | |
H1B | −0.116 (5) | 1.2086 (19) | 0.0295 (17) | 0.047 (8)* | |
O6 | 0.3343 (3) | 1.20229 (9) | 0.04220 (9) | 0.0271 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0167 (7) | 0.0228 (7) | 0.0189 (6) | −0.0005 (6) | 0.0032 (6) | 0.0034 (6) |
C1 | 0.0177 (10) | 0.0224 (10) | 0.0192 (9) | −0.0009 (9) | −0.0006 (9) | 0.0024 (8) |
O1 | 0.0188 (8) | 0.0282 (7) | 0.0190 (7) | −0.0007 (7) | 0.0000 (6) | −0.0013 (6) |
C7 | 0.0256 (12) | 0.0269 (11) | 0.0210 (10) | 0.0011 (10) | 0.0017 (9) | −0.0006 (9) |
O7 | 0.0232 (9) | 0.0419 (10) | 0.0318 (8) | 0.0031 (8) | 0.0030 (8) | −0.0069 (7) |
C8 | 0.0309 (13) | 0.0391 (13) | 0.0271 (11) | −0.0080 (11) | −0.0010 (10) | −0.0056 (10) |
C2 | 0.0190 (10) | 0.0208 (10) | 0.0181 (9) | −0.0010 (8) | 0.0001 (8) | 0.0033 (8) |
O2 | 0.0249 (8) | 0.0235 (7) | 0.0231 (7) | 0.0009 (7) | 0.0003 (7) | 0.0071 (6) |
C9 | 0.0372 (14) | 0.0197 (11) | 0.0197 (10) | 0.0004 (10) | 0.0068 (10) | 0.0001 (8) |
O8 | 0.0335 (10) | 0.0362 (9) | 0.0356 (9) | −0.0068 (8) | 0.0083 (8) | 0.0078 (8) |
C10 | 0.0499 (16) | 0.0284 (12) | 0.0281 (11) | 0.0066 (12) | 0.0041 (13) | 0.0091 (10) |
C3 | 0.0182 (10) | 0.0181 (10) | 0.0178 (9) | −0.0002 (9) | 0.0003 (8) | −0.0025 (7) |
O3 | 0.0198 (7) | 0.0189 (7) | 0.0212 (7) | −0.0016 (6) | 0.0026 (6) | −0.0031 (6) |
C11 | 0.0196 (10) | 0.0223 (10) | 0.0181 (9) | 0.0050 (9) | 0.0012 (9) | 0.0037 (8) |
O9 | 0.0173 (8) | 0.0403 (9) | 0.0295 (8) | 0.0013 (7) | −0.0007 (7) | −0.0031 (7) |
C12 | 0.0308 (12) | 0.0243 (10) | 0.0252 (11) | 0.0036 (11) | 0.0023 (10) | −0.0014 (9) |
C4 | 0.0147 (10) | 0.0197 (9) | 0.0180 (9) | −0.0023 (8) | 0.0025 (8) | 0.0011 (8) |
O4 | 0.0145 (7) | 0.0224 (7) | 0.0179 (6) | −0.0021 (6) | 0.0013 (6) | 0.0032 (6) |
C13 | 0.0203 (11) | 0.0197 (10) | 0.0175 (9) | −0.0012 (9) | 0.0006 (9) | 0.0002 (8) |
O10 | 0.0181 (8) | 0.0342 (9) | 0.0230 (8) | −0.0009 (7) | −0.0035 (6) | 0.0059 (7) |
C14 | 0.0208 (11) | 0.0324 (11) | 0.0213 (10) | −0.0055 (10) | 0.0012 (9) | 0.0047 (9) |
C5 | 0.0163 (10) | 0.0212 (10) | 0.0179 (9) | −0.0022 (9) | 0.0023 (8) | 0.0006 (8) |
C6 | 0.0238 (11) | 0.0173 (10) | 0.0194 (9) | −0.0013 (9) | −0.0005 (9) | −0.0011 (8) |
N1 | 0.0227 (10) | 0.0213 (9) | 0.0279 (10) | 0.0022 (8) | −0.0002 (8) | 0.0056 (8) |
O6 | 0.0271 (9) | 0.0207 (7) | 0.0333 (8) | −0.0030 (7) | 0.0008 (7) | 0.0032 (7) |
Geometric parameters (Å, º) top
O5—C1 | 1.410 (2) | C3—H3 | 1.000 |
O5—C5 | 1.432 (2) | O3—C11 | 1.355 (2) |
C1—O1 | 1.429 (2) | C11—O9 | 1.201 (3) |
C1—C2 | 1.530 (3) | C11—C12 | 1.497 (3) |
C1—H1 | 1.000 | C12—H12A | 0.980 |
O1—C7 | 1.371 (3) | C12—H12B | 0.980 |
C7—O7 | 1.200 (3) | C12—H12C | 0.980 |
C7—C8 | 1.485 (3) | C4—O4 | 1.435 (2) |
C8—H8A | 0.980 | C4—C5 | 1.534 (3) |
C8—H8B | 0.980 | C4—H4 | 1.000 |
C8—H8C | 0.980 | O4—C13 | 1.367 (2) |
C2—O2 | 1.446 (2) | C13—O10 | 1.198 (3) |
C2—C3 | 1.522 (3) | C13—C14 | 1.492 (3) |
C2—H2 | 1.000 | C14—H14A | 0.980 |
O2—C9 | 1.356 (3) | C14—H14B | 0.980 |
C9—O8 | 1.204 (3) | C14—H14C | 0.980 |
C9—C10 | 1.498 (3) | C5—C6 | 1.517 (3) |
C10—H10A | 0.980 | C5—H5 | 1.000 |
C10—H10B | 0.980 | C6—O6 | 1.231 (3) |
C10—H10C | 0.980 | C6—N1 | 1.332 (3) |
C3—O3 | 1.454 (2) | N1—H1A | 0.92 (3) |
C3—C4 | 1.519 (3) | N1—H1B | 0.87 (3) |
| | | |
C1—O5—C5 | 112.31 (16) | C11—O3—C3 | 118.47 (16) |
O5—C1—O1 | 109.78 (15) | O9—C11—O3 | 123.95 (18) |
O5—C1—C2 | 110.76 (15) | O9—C11—C12 | 125.3 (2) |
O1—C1—C2 | 108.65 (17) | O3—C11—C12 | 110.74 (19) |
O5—C1—H1 | 109.2 | C11—C12—H12A | 109.5 |
O1—C1—H1 | 109.2 | C11—C12—H12B | 109.5 |
C2—C1—H1 | 109.2 | H12A—C12—H12B | 109.5 |
C7—O1—C1 | 115.11 (15) | C11—C12—H12C | 109.5 |
O7—C7—O1 | 122.7 (2) | H12A—C12—H12C | 109.5 |
O7—C7—C8 | 126.3 (2) | H12B—C12—H12C | 109.5 |
O1—C7—C8 | 111.06 (19) | O4—C4—C3 | 106.92 (16) |
C7—C8—H8A | 109.5 | O4—C4—C5 | 110.79 (15) |
C7—C8—H8B | 109.5 | C3—C4—C5 | 108.70 (15) |
H8A—C8—H8B | 109.5 | O4—C4—H4 | 110.1 |
C7—C8—H8C | 109.5 | C3—C4—H4 | 110.1 |
H8A—C8—H8C | 109.5 | C5—C4—H4 | 110.1 |
H8B—C8—H8C | 109.5 | C13—O4—C4 | 116.86 (16) |
O2—C2—C3 | 106.22 (17) | O10—C13—O4 | 122.98 (19) |
O2—C2—C1 | 110.57 (15) | O10—C13—C14 | 125.93 (18) |
C3—C2—C1 | 113.58 (17) | O4—C13—C14 | 111.09 (18) |
O2—C2—H2 | 108.8 | C13—C14—H14A | 109.5 |
C3—C2—H2 | 108.8 | C13—C14—H14B | 109.5 |
C1—C2—H2 | 108.8 | H14A—C14—H14B | 109.5 |
C9—O2—C2 | 116.10 (18) | C13—C14—H14C | 109.5 |
O8—C9—O2 | 122.9 (2) | H14A—C14—H14C | 109.5 |
O8—C9—C10 | 126.4 (2) | H14B—C14—H14C | 109.5 |
O2—C9—C10 | 110.7 (2) | O5—C5—C6 | 110.20 (17) |
C9—C10—H10A | 109.5 | O5—C5—C4 | 107.48 (15) |
C9—C10—H10B | 109.5 | C6—C5—C4 | 112.21 (16) |
H10A—C10—H10B | 109.5 | O5—C5—H5 | 109.0 |
C9—C10—H10C | 109.5 | C6—C5—H5 | 109.0 |
H10A—C10—H10C | 109.5 | C4—C5—H5 | 109.0 |
H10B—C10—H10C | 109.5 | O6—C6—N1 | 125.5 (2) |
O3—C3—C4 | 107.74 (15) | O6—C6—C5 | 117.67 (19) |
O3—C3—C2 | 105.76 (16) | N1—C6—C5 | 116.85 (19) |
C4—C3—C2 | 111.53 (17) | C6—N1—H1A | 120.9 (18) |
O3—C3—H3 | 110.6 | C6—N1—H1B | 122 (2) |
C4—C3—H3 | 110.6 | H1A—N1—H1B | 116 (3) |
C2—C3—H3 | 110.6 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O6i | 0.87 (3) | 1.99 (3) | 2.840 (3) | 165 (3) |
C2—H2···O9ii | 1.00 | 2.29 | 3.168 (3) | 146 |
C8—H8C···O7iii | 0.98 | 2.55 | 3.366 (3) | 141 |
C12—H12C···O7iv | 0.98 | 2.60 | 3.392 (3) | 138 |
C14—H14A···O6v | 0.98 | 2.57 | 3.529 (3) | 166 |
C14—H14C···O10iii | 0.98 | 2.46 | 3.283 (3) | 142 |
N1—H1A···O5 | 0.92 (3) | 2.29 (3) | 2.658 (2) | 103 (2) |
C3—H3···O9 | 1.00 | 2.36 | 2.734 (3) | 101 |
C4—H4···O10 | 1.00 | 2.32 | 2.682 (2) | 100 |
C5—H5···O1 | 1.00 | 2.36 | 2.776 (2) | 104 |
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+1/2, −y+2, z−1/2; (v) x+1/2, −y+5/2, −z. |